[ CAS No. 470-69-9 ] {[proInfo.proName]}

Name: 470-69-9|(2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-2-((((2R,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol|98+%
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Quality Control of [ 470-69-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 470-69-9 ]

Product Details of [ 470-69-9 ]

CAS No. :	470-69-9	MDL No. :	MFCD16660341
Formula :	C₁₈H₃₂O₁₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VAWYEUIPHLMNNF-OESPXIITSA-N
M.W :	504.44	Pubchem ID :	440080
Synonyms :	1F-beta-D-Fructosylsucrose

Safety of [ 470-69-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 470-69-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 470-69-9 ]
Downstream synthetic route of [ 470-69-9 ]

[ 470-69-9 ] Synthesis Path-Upstream 1~11

1
[ 7512-17-6 ]
[ 57-50-1 ]
[ 84039-32-7 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Yield	Reaction Conditions	Operation in experiment
22.1%	With Aspergillus oryzae NBRC₁₀₀₉₅₉ mycelia In citrate buffer at 30℃; for 8 h; Enzymatic reaction	The hydrolytic activity of β-fructofuranosidase was assayed using sucrose as a substrate, and was monitored by measuring the amount of reducing sugar released from sucrose. The enzyme solution (50 μL) was added to 50 μL of 0.4percent sucrose in 20 mM Na citrate buffer (pH 5.5) and the mixture was incubated at 30 °C. After incubation, the enzymatic reaction was stopped by heating the sample at 95 °C for 5 min. The amount of reducing sugar in the reaction mixture was determined by the Somogyi-Nelson method using glucose as a standard.²² One unit (U) of enzyme activity was defined as the amount of enzyme required to hydrolyze 1 μmol of sucrose per minute under the assay conditions.

Reference： [1] Carbohydrate Research, 2012, vol. 353, p. 27 - 32

2
[ 57-50-1 ]
[ 57-48-7 ]
[ 59432-60-9 ]
[ 50-99-7 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Yield	Reaction Conditions	Operation in experiment
29.89 %Chromat.	With Aspergillus flavus NFCCI 2364 culture filtrate In aq. buffer at 55℃; for 24 h; Microbiological reaction	General procedure: FOS production was carried out by adding 1ml of enzyme samples collected at various time intervals to 3ml of 50percent (w/v) sucrose dissolved in 0.1M citrate buffer (pH 5.5) for period of 24h at 55°C. The amount of FOS formation in the samples was analyzed by high performance liquid chromatography (HPLC, Waters) with sugar-pak column (6.5×300mm) and refractive index (RI) differential detector (RI 2414).
25.31 %Chromat.	With Aspergillus niger SI 19 culture filtrate In aq. buffer at 55℃; for 24 h; Microbiological reaction	General procedure: FOS production was carried out by adding 1ml of enzyme samples collected at various time intervals to 3ml of 50percent (w/v) sucrose dissolved in 0.1M citrate buffer (pH 5.5) for period of 24h at 55°C. The amount of FOS formation in the samples was analyzed by high performance liquid chromatography (HPLC, Waters) with sugar-pak column (6.5×300mm) and refractive index (RI) differential detector (RI 2414).

Reference： [1] Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 97, p. 12 - 17
[2] Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 97, p. 12 - 17

3
[ 57-50-1 ]
[ 57-48-7 ]
[ 50-99-7 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Reference： [1] Journal of Molecular Catalysis B: Enzymatic, 2015, vol. 111, p. 51 - 55

4
[ 57-50-1 ]
[ 2280-44-6 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Reference： [1] Tetrahedron Asymmetry, 2016, vol. 27, # 24, p. 1245 - 1252

5
[ 57-50-1 ]
[ 50-99-7 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Reference： [1] Journal of Biotechnology, 2017, vol. 249, p. 25 - 33

6
[ 470-69-9 ]
[ 13101-54-7 ]
[ 13133-07-8 ]

Reference： [1] Bioscience, Biotechnology and Biochemistry, 2002, vol. 66, # 6, p. 1419 - 1422

7
[ 57-50-1 ]
[ 2280-44-6 ]
[ 59432-60-9 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Reference： [1] Carbohydrate Research, 2008, vol. 343, # 1, p. 56 - 66

8
[ 57-50-1 ]
[ 57-48-7 ]
[ 50-99-7 ]
[ 56-81-5 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2008, vol. 56, # 8, p. 2805 - 2809

9
[ 57-50-1 ]
[ 59432-60-9 ]
[ 50-99-7 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Reference： [1] Journal of Biotechnology, 2017, vol. 249, p. 25 - 33
[2] Journal of Molecular Catalysis B: Enzymatic, 2012, vol. 76, p. 44 - 51

10
[ 57-50-1 ]
[ 492-62-6 ]
[ 470-23-5 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2013, vol. 61, # 50, p. 12265 - 12273

11
[ 57-50-1 ]
[ 59432-60-9 ]
[ 137855-42-6 ]
[ 470-69-9 ]
[ 562-68-5 ]
[ 13133-07-8 ]

Reference： [1] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 109, p. 85 - 93

[ 470-69-9 ] Synthesis Path-Downstream 1~47

1
[ 57-50-1 ]
[ 470-69-9 ]

Yield	Reaction Conditions	Operation in experiment
	mit Hilfe von Enzym-Praeparaten aus Aspergillus oryzae;
	mit Hilfe von Enzym-Praeparaten aus Aspergillus niger;
	mit Hilfe von Enzym-Praeparaten aus Aspergillus flavus;

	mit Hilfe von Enzym-Praeparaten aus Penicillium chrysogenum;
	mit Hilfe von Enzym-Praeparaten aus Aerobacter laevanicum;
	mit Hilfe von Enzym-Praeparaten aus Corynebacterium-Art;
	mit Hilfe von Invertase-Praeparaten aus Hefe;
	mit Hilfe von Invertase-Praeparaten aus Isotricha;
	mit Hilfe eines Enzym-Praeparats aus Beta vulgaris;
	With Scopulariopsis brevicaulis enzyme Enzymatic reaction;

Reference： [1]Bacon; Bell [Journal of the Chemical Society, 1953, p. 2528] Pazur [Journal of Biological Chemistry, 1952, vol. 199, p. 217,219] Kurasawa et al. [Nippon Nogeikagaku Kaishi, 1956, vol. 30, p. 624,625, 629][Chem.Abstr., 1958, p. 20376]
[2]Barker et al. [Journal of the Chemical Society, 1954, p. 2125,2126]
[3]Giri et al. [Journal of the Indian Institute of Science, Section A, 1954, vol. 36, p. 259,262]
[4]Ballio; Russi [Gazzetta Chimica Italiana, 1956, vol. 86, p. 476,477]
[5]Feingold et al. [Biochemical Journal, 1956, vol. 64, p. 351,353, 357]
[6]Avigad; Feingold [Archives of Biochemistry, 1957, vol. 70, p. 178,179]
[7]Gross et al. [Journal of the Chemical Society, 1954, p. 1727,1728, 1729] Bacon [Biochemical Journal, 1954, vol. 57, p. 320,323]
[8]Howard [Biochemical Journal, 1959, vol. 71, p. 675,677]
[9]Allen; Bacon [Biochemical Journal, 1956, vol. 63, p. 200,202]
[10]Location in patent: scheme or table Okada, Hideki; Fukushi, Eri; Yamamori, Akira; Kawazoe, Naoki; Onodera, Shuichi; Kawabata, Jun; Shiomi, Norio [Carbohydrate Research, 2011, vol. 346, # 16, p. 2633 - 2637]

2
[ 108-24-7 ]
[ 470-69-9 ]
[ 25101-98-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With pyridine at 20℃;	1′′,2,3,3′,3′′,4,4′,4′′,6,6′,6′′-Undeca-O-acetyl-deoxy-1-kestose (3).15,18 Solution of 1-kestose (1, 0.03 g, 0.06 mmol) in pyridine (15 mL) was treated with acetic anhydride (1 mL, 10.7 mmol), and the mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure and subjected to column chromatography on silica gel by elution with chloroform to yield 3 (0.055 g, 96%) as a colorless liquid. [α]D + 30.2 (c = 1.0, CHCl3); Ref. 16 [α]D +31.8 (c = 3.7, CHCl3). 1H-NMR (500 MHz, CDCl3) δ: 5.75 (1H, d, J1,2 3.4 Hz, H-1), 5.69 (1H, d, J3′,4′ 8.0 Hz, H-3′), 5.48 (1H, d, J3′′,4′′ 6.9 Hz, H-3′′), 5.46 (1H, t, J3′,4′ 8.0 Hz, H-4′), 5.42 (1H, t, J3,4 9.7 Hz, H-3), 5.34 (1H, t, J3′′,4′′ 6.9 Hz, H-4′′), 5.08 (1H, t, J3,4 9.7 Hz, H-4), 4.91 (1H, dd, J1,2 3.4 Hz, J2,3 10.3 Hz, H-2), 4.39-4.33 (3H, m, H-5, H-6′′), 4.33-4.24 (3H, m, H-6a, H-6′), 4.24-4.20 (3H, m, H-1′′, H-5′), 4.20-4.14 (2H, m, H-6b, H-5′′), 3.69 (1H, d, J1′a,1′b 9.2 Hz, H-1′a), 3.63 (1H, d, J1′a,1′b 9.2 Hz, H-1′b), 2.19-2.14 (3H, m, CH3), 2.13-2.12 (6H, m, 2 x CH3), 2.11-2.09 (15H, m, 5 x CH3), 2.06 (3H, s, CH3), 2.04 (3H, s, CH3), 2.01 (3H, s, CH3) ppm. 13C-NMR (125 MHz, CDCl3) δ: 170.7, 170.6, 170.5, 170.1, 169.9, 169.7, 169.6 (C=O), 103.4 (C-2′), 102.9 (C-2′′), 89.2 (C-1), 78.4 (C-5′′), 77.8 (C-5′), 76.5 (C-3′′), 75.5 (C-4′′), 74.9 (C-3′), 73.7 (C-4′), 70.0 (C-2), 69.8 (C-3), 68.2 (C-5), 68.2 (C-4), 63.7 (C-6′′), 63.2 (C-6′), 62.7 (C-1′′), 62.2 (C-1′), 61.7(C-6), 20.8, 20.7, 20.7, 20.6, 20.6, 20.5 (CH3) ppm. HRMS (ESI): calcd. for C40H54O27Na 989.2750 [M + Na]+; found 989.2797.
	In pyridine for 168h;

Reference： [1]Tachrim, Zetryana Puteri; Nakamura, Tadashi; Sakihama, Yasuko; Hashidoko, Yasuyuki; Hashimoto, Makoto [Arkivoc, 2018, vol. 2018, # 7, p. 341 - 348]
[2]Rakhmanberdyeva, R. K.; Rashkes, Ya. V.; Rakhimov, D. A. [Chemistry of Natural Compounds, 1986, vol. 22, # 2, p. 135 - 140][Khimiya Prirodnykh Soedinenii, 1986, vol. 22, # 2, p. 146 - 151]

3
[ 470-69-9 ]
[ 6347-01-9 ]

Yield	Reaction Conditions	Operation in experiment
	With water at 37℃; for 0.0833333h; exo-inulinase from Penicillium trzebinskii, substrate specificity and subsite affinity;

Reference： [1]Onodera, Shuichi; Shiomi, Norio [Bioscience, Biotechnology and Biochemistry, 1992, vol. 56, # 9, p. 1443 - 1447]

4
[ 57-50-1 ]
α-D-fructofuranosyl-(2->6)-D-glucopyranose [ No CAS ]
[ 138809-75-3 ]
[ 470-69-9 ]
[ 562-68-5 ]

Yield	Reaction Conditions	Operation in experiment
	at 100℃; Further byproducts given;

Reference： [1]Manley-Harris; Richards [Carbohydrate Research, 1991, vol. 219, # 1, p. 101 - 113]

5
[ 57-50-1 ]
[ 138809-75-3 ]
[ 138809-76-4 ]
[ 470-69-9 ]
[ 562-68-5 ]

Yield	Reaction Conditions	Operation in experiment
	at 100℃; Further byproducts given;

Reference： [1]Manley-Harris; Richards [Carbohydrate Research, 1991, vol. 219, # 1, p. 101 - 113]

6
[ 470-69-9 ]
[ 74-88-4 ]
[ 24807-72-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In N,N-dimethyl-formamide for 18h; Ambient temperature;
	Stage #1: 1-kestose With sodium hydride In dimethyl sulfoxide at 20℃; Inert atmosphere; Stage #2: methyl iodide In dimethyl sulfoxide for 15h; Inert atmosphere;	Methylation and methanolysis Methylation of saccharides was carried out using the method describedby Hakomori.32 Solution of reference saccharides (3-5 mg) or kestose isomers (1-5 mg) in 1 mL of dimethyl sulfoxide (DMSO) were prepared with stirring under a nitrogen atmosphere.To prepare the carbanion solution, a mixture of 500 mg ofsodium hydride and 5 mL of DMSO was stirred in a flask under anitrogen atmosphere for 1 h at 50 °C. A 1-mL aliquot of the latter solution was added to 1 mL of the former and stirred for 3.5-5.0 hat 20 °C. Subsequently, 0.8 mL of methyl iodide was added and the solution stirred for an additional 15 h. The reaction mixture wasdiluted with water and extracted with chloroform. The chloroform extract was washed with water and concentrated in vacuo to give the methylated products in a syrupy residue. The permethylated saccharides were methanolysed by heating with 1.5% methanolichydrochloric acid at 92 °C for 5-20 min. The reaction mixture wastreated with Amberlite IRA-410 (OH-) to remove hydrochloric acidand evaporated in vacuo to dryness. The resulting methanolysate was dissolved in a small quantity of methanol or chloroform prior to GC-FID or GC-MS analyses.

Reference： [1]Timmermans; Bogaert; De Wit; Vliegenthart [Journal of Carbohydrate Chemistry, 1997, vol. 16, # 7, p. 1145 - 1158]
[2]Shiomi, Norio; Abe, Tatsuya; Kikuchi, Hiroto; Aritsuka, Tsutomu; Takata, Yusuke; Fukushi, Eri; Fukushi, Yukiharu; Kawabata, Jun; Ueno, Keiji; Onodera, Shuichi [Carbohydrate Research, 2016, vol. 424, p. 1 - 7]

Yield	Reaction Conditions	Operation in experiment
	Hydrolyse m. β-Fructofuranosidase;
	Hydrolyse m. Oxals.;
	Hydrolyse m. HCl;

	Methyl., anschl. CH3OH / HCl (GC);
	at 37℃; yeast invertase; rate of disappearance; other kestoses;

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid

10
[ 57-50-1 ]
[ 138809-75-3 ]
[ 138809-76-4 ]
[ 138809-77-5 ]
[ 470-69-9 ]
[ 3688-75-3 ]
[ 562-68-5 ]

Yield	Reaction Conditions	Operation in experiment
	at 100℃; relative rates of formation;

Reference： [1]Manley-Harris; Richards [Carbohydrate Research, 1991, vol. 219, # 1, p. 101 - 113]

11
[ 470-69-9 ]
[ 13101-54-7 ]
[ 13133-07-8 ]
O-β-D-fructofuranosyl-(2->1)-O-β-D-fructofuranosyl-(2->1)-O-[β-D-galactopyranosyl-(1->4)]-α-D-glucopyranoside [ No CAS ]
O-β-D-fructofuranosyl-(2->1)-O-β-D-fructofuranosyl-(2->1)-O-β-D-fructofuranosyl-(2->1)-O-[β-D-galactopyranosyl-(1->4)]-α-D-glucopyranoside [ No CAS ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,2002,vol. 66,p. 1419 - 1422

12
Lactose [ No CAS ]
[ 470-69-9 ]
O-β-D-fructofuranosyl-(2->1)-O-β-D-fructofuranosyl-(2->1)-O-[β-D-galactopyranosyl-(1->4)]-α-D-glucopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With β-galactosidase from Bacillus circulans (EC 3.2.1.23) In acetate buffer at 55℃; for 2h;

Reference： [1]Farkas, Erzsébet; Schmidt, Ulja; Thiem, Joachim; Kowalczyk, Jörg; Kunz, Markwart; Vogel, Manfred [Synthesis, 2003, # 5, p. 699 - 706]

13
[ 470-69-9 ]
β-D-glucose 1-phosphate [ No CAS ]
2-α-D-glucosyl isokestose [ No CAS ]
2(2-α-D-glucosyl)₂ isokestose [ No CAS ]
2(2-α-D-glucosyl)₃ isokestose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 2.59 g 2: 306.3 mg 3: 18.8 mg	With kojibiose phosphorylase In acetate buffer at 50℃; for 48h;

Reference： [1]Okada, Hideki; Fukushi, Eri; Onodera, Shuichi; Nishimoto, Tomoyuki; Kawabata, Jun; Kikuchi, Masanori; Shiomi, Norio [Carbohydrate Research, 2003, vol. 338, # 9, p. 879 - 885]

14
[ 470-69-9 ]
D-fructose [ No CAS ]
[ 57-50-1 ]

Yield	Reaction Conditions	Operation in experiment
	With aqueous buffer at 80℃;

Reference： [1]L'Homme; Arbelot; Puigserver; Biagini, Anne [Journal of Agricultural and Food Chemistry, 2003, vol. 51, # 1, p. 224 - 228]

15
[ 13133-07-8 ]
[ 470-23-5 ]
[ 470-69-9 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2003,vol. 51,p. 224 - 228

16
Lactose [ No CAS ]
[ 470-69-9 ]
β-D-galactopyranosyl-(1->3)-α-D-glucopyranosyl-(1<->2)-β-D-fructofuranosyl-(1<->2)-β-D-fructofuranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7%	With β-galactosidase from bovine testes EC 3.2.1.23; Na₂H₂PO₄*12H₂O; citric acid at 37℃; for 48h;

Reference： [1]Schröder, Sven; Schmidt, Ulja; Thiem, Joachim; Kowalczyk, Jörg; Kunz, Markwart; Vogel, Manfred [Tetrahedron, 2004, vol. 60, # 11, p. 2601 - 2608]

17
[ 2146-71-6 ]
[ 470-69-9 ]
2-O-lauroyl(1-kestose) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With metalloprotease thermolysin on Celite In dimethyl sulfoxide at 45℃; for 72h;

Reference： [1]Pérez-Victoria, Ignacio; Morales, Juan Carlos [Tetrahedron, 2006, vol. 62, # 10, p. 2361 - 2369]

18
[ 2146-71-6 ]
[ 470-69-9 ]
6''-O-lauroyl(1-kestose) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With pyridine; Novozym 435; 3 A molecular sieve In <i>tert</i>-butyl alcohol at 60℃; for 72h;

Reference： [1]Pérez-Victoria, Ignacio; Morales, Juan Carlos [Tetrahedron, 2006, vol. 62, # 5, p. 878 - 886]

19
[ 2146-71-6 ]
[ 470-69-9 ]
6''-O-lauroyl(1-kestose) [ No CAS ]
6-O-lauroyl(1-kestose) [ No CAS ]
6'-O-lauroyl(1-kestose) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With pyridine; MβCD-subtilisin Carlsberg at 40℃; for 48h;

Reference： [1]Pérez-Victoria, Ignacio; Morales, Juan Carlos [Tetrahedron, 2006, vol. 62, # 5, p. 878 - 886]

20
[ 2146-71-6 ]
[ 470-69-9 ]
6-O-lauroyl(1-kestose) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With pyridine; 3 A molecular sieve; Thermomyces lanuginosis lipase In <i>tert</i>-butyl alcohol at 60℃; for 72h;

Reference： [1]Pérez-Victoria, Ignacio; Morales, Juan Carlos [Tetrahedron, 2006, vol. 62, # 5, p. 878 - 886]

21
[ 57-50-1 ]
[ 2280-44-6 ]
[ 59432-60-9 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Reference： [1]Carbohydrate Research,2008,vol. 343,p. 56 - 66

22
inulin [ No CAS ]
[ 67-47-0 ]
[ 57-48-7 ]
[ 59432-60-9 ]
[ 50-99-7 ]
[ 81129-73-9 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Yield	Reaction Conditions	Operation in experiment
	With water;phosphoric acid; at 50 - 95℃; for 0.25 - 0.75h;pH 1.75 - 3.75;	Figure 4, from a second laboratorial work, is a TLC - Thin Layer Chromatography on silicagel 60 (Merck) developed with the mixture isopropanol : ethyl acetate : water 5:1 :2 as mobile phase and with partial runs of 1/3, 2/3, and 3/3 of the front line and developed with orcinol : sulfuric acid : methanol at 1000C for 5 minutes. This figure illustrates the profile of FOS - Fructooligosaccharides when one hydrolyzes purified inulin from dahlia roots (5g%) with phosphoric acid at pH = 2.5 at 850C during 15 minutes (15), 30 minutes (30), and 45 minutes (45), indicating that the modulation of a single kinetic parameter - time of hydrolysis - already allows to govern the quantitative relation of FOS > fructose (cases 15 and 30) or the opposite (FOS < fructose; 45). A similar strategy for FOS > fructose may also be governed by the other parameters (pH itself or temperature of hydrolysis), as shown for hydrolysis of inulin with phosphoric or citric acids at pHs from 1.75 to 3.75 in the range of 5O0C to 95oC (as better explained in Figure 5). In Figure 4, (f) and (g) denotes for free fructose and glucose, respectively. GP refers to the Degree of Polymerization. It is remarkable that phosphoric or citric hydrolyses of inulin may be effectively addressed <n="27"/>to the preferential preparation of FOS - Fructooligosaccharides since when addressed to a higher fructose content (lane 45), some amount of the co-product HMF - hydroxymethylfurfural turns clearly visible in the front zone of the chromatogram. Its companion spot most probably is a DFA (difructose anhydride).; Figure 5 is a bar graphic comparing the effect of the kinetic parameters such as temperature and time of hydrolysis once fixed the hidrogenionic potential at pH = 2.5 and their respective capacities for the modulation on the qualitative nature of the products from the hydrolyses of dahlia inulin with phosphoric or citric acids when the substrate is used at a concentration of 5g%. According to the intended innovation in this patent request - the preferential production of FOS or FrutoOligoSaccharides - is obviously that, for each range of temperature, namely, 750C, 850C ou 950C, either in the phosphoric or in the citric hydrolyses, the formation of FOS is preferential in (8x2 =) 16 assays, except for those two - at 950C and during 25 minutes - where fructose shows predominance with respect to FOS. Incidentally, those two exceptional conditions - which are not the scope of this patent request - also led to the formation of some HMF - hydroxymethylfurfural - undesirable in a inulin hydrolysis, with the attenuating condition that a less expensive practice as activated charcoal is able to remove the contaminant HMF. Concerning the reaction yield reported to the initial inulin input, the diluted phosphoric acid guarantees in the times of 25 min at 850C and of 15 min at 950C percentages of hydrolyses up to 80%, being the most of the products - 76% and 63%, respectively - FOS or frutooligosaccharides and being the remaining fructose since HMF is no longer detected under these conditions of hydrolysis. The same approach is attained with citric acid although with somewhat reduced yields - 64% or 76%, but even so FOS correspond to 78% and 74% of the hydrolysis products.; Figure 6 derives from another practical example of laboratory work, namely a high performance liquid chromatography or HPLC in a column of 10 micra microparticles of silica gel derivatized with amino groups and provided by Spectraphysics. Twenty microliters of a citric hydrolyzate of inulin at 10% obtained at pH 2.5 during 5 or 15 minutes at 850C were applied to the column and elution proceeded with 70% acetonitrile at a 1 mL/min flow rate and the monitoring was carried out with DRI- differential refraction index. It is shown that in both conditions <n="28"/>- 5 and 15 minutes - inulin is converted, by citric acid, into a family of FOS - FructoOligoSaccharides with DP - Degree of Polymerization - 3 to 18 or more (considering the analytical capacity of the referred column), still emphazing that fructose, with respect to FOS concentration, contributes with a maximum of 25% and a minimum of 5%.; Figure 7, resulting from another practical laboratory work, is also - like Figure 6 - a HPLC but carried out with samples arising from phosphoric acid hydrolyses under the same conditions of those described in Figure 6. The qualitative profiles for FOS are quite similar in both figures. In 8 of 9 assays, FOS predominates. In the nineth - 25 minutes of hydrolysis at higher temperature - FOS and fructose contents are more or less equivalent.

Reference： [1]Patent: WO2009/6715,2009,A2 .Location in patent: Page/Page column 25-27

23
inulin [ No CAS ]
[ 67-47-0 ]
[ 57-48-7 ]
[ 59432-60-9 ]
[ 81129-73-9 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Yield	Reaction Conditions	Operation in experiment
	With water;citric acid; at 50 - 95℃; for 0.25 - 0.75h;pH 1.75 - 3.75;	Figure 4, from a second laboratorial work, is a TLC - Thin Layer Chromatography on silicagel 60 (Merck) developed with the mixture isopropanol : ethyl acetate : water 5:1 :2 as mobile phase and with partial runs of 1/3, 2/3, and 3/3 of the front line and developed with orcinol : sulfuric acid : methanol at 1000C for 5 minutes. This figure illustrates the profile of FOS - Fructooligosaccharides when one hydrolyzes purified inulin from dahlia roots (5g%) with phosphoric acid at pH = 2.5 at 850C during 15 minutes (15), 30 minutes (30), and 45 minutes (45), indicating that the modulation of a single kinetic parameter - time of hydrolysis - already allows to govern the quantitative relation of FOS > fructose (cases 15 and 30) or the opposite (FOS < fructose; 45). A similar strategy for FOS > fructose may also be governed by the other parameters (pH itself or temperature of hydrolysis), as shown for hydrolysis of inulin with phosphoric or citric acids at pHs from 1.75 to 3.75 in the range of 5O0C to 95oC (as better explained in Figure 5). In Figure 4, (f) and (g) denotes for free fructose and glucose, respectively. GP refers to the Degree of Polymerization. It is remarkable that phosphoric or citric hydrolyses of inulin may be effectively addressed <n="27"/>to the preferential preparation of FOS - Fructooligosaccharides since when addressed to a higher fructose content (lane 45), some amount of the co-product HMF - hydroxymethylfurfural turns clearly visible in the front zone of the chromatogram. Its companion spot most probably is a DFA (difructose anhydride).; Figure 5 is a bar graphic comparing the effect of the kinetic parameters such as temperature and time of hydrolysis once fixed the hidrogenionic potential at pH = 2.5 and their respective capacities for the modulation on the qualitative nature of the products from the hydrolyses of dahlia inulin with phosphoric or citric acids when the substrate is used at a concentration of 5g%. According to the intended innovation in this patent request - the preferential production of FOS or FrutoOligoSaccharides - is obviously that, for each range of temperature, namely, 750C, 850C ou 950C, either in the phosphoric or in the citric hydrolyses, the formation of FOS is preferential in (8x2 =) 16 assays, except for those two - at 950C and during 25 minutes - where fructose shows predominance with respect to FOS. Incidentally, those two exceptional conditions - which are not the scope of this patent request - also led to the formation of some HMF - hydroxymethylfurfural - undesirable in a inulin hydrolysis, with the attenuating condition that a less expensive practice as activated charcoal is able to remove the contaminant HMF. Concerning the reaction yield reported to the initial inulin input, the diluted phosphoric acid guarantees in the times of 25 min at 850C and of 15 min at 950C percentages of hydrolyses up to 80%, being the most of the products - 76% and 63%, respectively - FOS or frutooligosaccharides and being the remaining fructose since HMF is no longer detected under these conditions of hydrolysis. The same approach is attained with citric acid although with somewhat reduced yields - 64% or 76%, but even so FOS correspond to 78% and 74% of the hydrolysis products.; Figure 6 derives from another practical example of laboratory work, namely a high performance liquid chromatography or HPLC in a column of 10 micra microparticles of silica gel derivatized with amino groups and provided by Spectraphysics. Twenty microliters of a citric hydrolyzate of inulin at 10% obtained at pH 2.5 during 5 or 15 minutes at 850C were applied to the column and elution proceeded with 70% acetonitrile at a 1 mL/min flow rate and the monitoring was carried out with DRI- differential refraction index. It is shown that in both conditions <n="28"/>- 5 and 15 minutes - inulin is converted, by citric acid, into a family of FOS - FructoOligoSaccharides with DP - Degree of Polymerization - 3 to 18 or more (considering the analytical capacity of the referred column), still emphazing that fructose, with respect to FOS concentration, contributes with a maximum of 25% and a minimum of 5%.

Reference： [1]Patent: WO2009/6715,2009,A2 .Location in patent: Page/Page column 25-27

24
[ 57-50-1 ]
[ 57-48-7 ]
[ 50-99-7 ]
[ 56-81-5 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2008,vol. 56,p. 2805 - 2809

25
[ 57-50-1 ]
[ 10489-79-9 ]
[ 470-23-5 ]
[βFruf(2-6)]2 [ No CAS ]
[ 470-69-9 ]
[ 3688-75-3 ]
[ 562-68-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium sulfate; potassium dihydrogenphosphate; ammonium nitrate; sodium chloride; calcium chloride In water at 32℃; for 192h; Enzymatic reaction; optical yield given as %de;

Reference： [1]Location in patent: experimental part Matulová, Mária; Husárová, Slavomíra; Capek, Peter; Sancelme, Martine; Delort, Anne-Marie [Carbohydrate Research, 2011, vol. 346, # 4, p. 501 - 507]

26
[ 57-50-1 ]
[ 59432-60-9 ]
[ 50-99-7 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Reference： [1]Journal of Biotechnology,2017,vol. 249,p. 25 - 33
[2]Journal of Molecular Catalysis B: Enzymatic,2012,vol. 76,p. 44 - 51

27
[ 7512-17-6 ]
[ 57-50-1 ]
[ 84039-32-7 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Yield	Reaction Conditions	Operation in experiment
22.1%	With Aspergillus oryzae NBRC100959 mycelia; In citrate buffer; at 30℃; for 8h;pH 5.5;Enzymatic reaction;	The hydrolytic activity of beta-fructofuranosidase was assayed using sucrose as a substrate, and was monitored by measuring the amount of reducing sugar released from sucrose. The enzyme solution (50 muL) was added to 50 muL of 0.4% sucrose in 20 mM Na citrate buffer (pH 5.5) and the mixture was incubated at 30 C. After incubation, the enzymatic reaction was stopped by heating the sample at 95 C for 5 min. The amount of reducing sugar in the reaction mixture was determined by the Somogyi-Nelson method using glucose as a standard.22 One unit (U) of enzyme activity was defined as the amount of enzyme required to hydrolyze 1 mumol of sucrose per minute under the assay conditions.

Reference： [1]Carbohydrate Research,2012,vol. 353,p. 27 - 32

28
[ 57-50-1 ]
[ 894412-30-7 ]
[ 470-69-9 ]
[ 562-68-5 ]

Yield	Reaction Conditions	Operation in experiment
	With β-fructofuranosidase from Schwanniomyces occidentalis mutant N254T at 50℃; for 24h; aq. acetate buffer; Enzymatic reaction;

Reference： [1]Location in patent: experimental part Alvaro-Benito, Miguel; Sainz-Polo, M. Angela; Gonzalez-Perez, David; Gonzalez, Beatriz; Plou, Francisco J.; Fernandez-Lobato, Maria; Sanz-Aparicio, Julia [Journal of Biological Chemistry, 2012, vol. 287, # 23, p. 19674 - 19686]

29
[ 57-50-1 ]
[ 470-69-9 ]
[ 562-68-5 ]

Yield	Reaction Conditions	Operation in experiment
	With β-fructofuranosidase from Schwanniomyces occidentalis at 50℃; for 24h; aq. acetate buffer; Enzymatic reaction;

30
[ 57-50-1 ]
[ 57-48-7 ]
[ 59432-60-9 ]
[ 50-99-7 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Yield	Reaction Conditions	Operation in experiment
8.25%Chromat.; 29.89%Chromat.; 25.26%Chromat.	With Aspergillus flavus NFCCI 2364 culture filtrate; In aq. buffer; at 55℃; for 24h;pH 5.5;Microbiological reaction;	General procedure: FOS production was carried out by adding 1ml of enzyme samples collected at various time intervals to 3ml of 50% (w/v) sucrose dissolved in 0.1M citrate buffer (pH 5.5) for period of 24h at 55C. The amount of FOS formation in the samples was analyzed by high performance liquid chromatography (HPLC, Waters) with sugar-pak column (6.5×300mm) and refractive index (RI) differential detector (RI 2414).
5.94%Chromat.; 23.74%Chromat.; 25.31%Chromat.	With Aspergillus niger SI 19 culture filtrate; In aq. buffer; at 55℃; for 24h;pH 5.5;Microbiological reaction;	General procedure: FOS production was carried out by adding 1ml of enzyme samples collected at various time intervals to 3ml of 50% (w/v) sucrose dissolved in 0.1M citrate buffer (pH 5.5) for period of 24h at 55C. The amount of FOS formation in the samples was analyzed by high performance liquid chromatography (HPLC, Waters) with sugar-pak column (6.5×300mm) and refractive index (RI) differential detector (RI 2414).

Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2013,vol. 97,p. 12 - 17
[2]Journal of Molecular Catalysis B: Enzymatic,2013,vol. 97,p. 12 - 17

31
[ 57-50-1 ]
[ 50-99-7 ]
[ 470-69-9 ]

Yield	Reaction Conditions	Operation in experiment
40.12 %Chromat.	With Penicillium islandicum MTCC 4926 culture filtrate In aq. buffer at 55℃; for 24h; Microbiological reaction;	2.6. Production and analysis of FOS General procedure: FOS production was carried out by adding 1ml of enzyme samples collected at various time intervals to 3ml of 50% (w/v) sucrose dissolved in 0.1M citrate buffer (pH 5.5) for period of 24h at 55°C. The amount of FOS formation in the samples was analyzed by high performance liquid chromatography (HPLC, Waters) with sugar-pak column (6.5×300mm) and refractive index (RI) differential detector (RI 2414).

Reference： [1]Ganaie, Mohd Anis; Gupta, Uma Shanker; Kango, Naveen [Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 97, p. 12 - 17]

32
[ 57-50-1 ]
[ 492-62-6 ]
[ 470-23-5 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2013,vol. 61,p. 12265 - 12273

33
[ 57-50-1 ]
[ 492-62-6 ]
[ 470-23-5 ]
[ 470-69-9 ]

Yield	Reaction Conditions	Operation in experiment
	With recombinant Erwinia amylovora levansucrase In aq. phosphate buffer at 37℃; for 1h; Enzymatic reaction;

Reference： [1]Caputi, Lorenzo; Nepogodiev, Sergey A.; Malnoy, Mickael; Rejzek, Martin; Field, Robert A.; Benini, Stefano [Journal of Agricultural and Food Chemistry, 2013, vol. 61, # 50, p. 12265 - 12273]

34
[ 57-50-1 ]
[ 59432-60-9 ]
levanohexaose [ No CAS ]
[ 137855-42-6 ]
[ 470-69-9 ]
[ 562-68-5 ]
[ 13133-07-8 ]

Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2014,vol. 109,p. 85 - 93

35
[ 57-50-1 ]
[ 57-48-7 ]
[ 50-99-7 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Yield	Reaction Conditions	Operation in experiment
	With Viscozyme L (-fructosyltransferase) immobilized on chitosan spheres; In aq. acetate buffer; at 50℃;pH 4.5;Flow reactor;	Production of invert sugar was carried using a solution of sucrose150 g/L diluted in 50 mM sodium acetate buffer pH 4.5. The solu-tion was pumped at flow rates of (0.5, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0,4.7) mL/min in both fluidized and packed bed reactors. Four bed vol-umes of solution were passed through the column before taking the sample to achieve stationary state. These experiments were carriedout in duplicate, changing the column bed at each experiment

Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2015,vol. 111,p. 51 - 55

36
[ 470-69-9 ]
[ 470-23-5 ]

Yield	Reaction Conditions	Operation in experiment
	With Penicillium oxalicum GXU20 β-fructofuranosidase at 50℃; for 0.25h; Enzymatic reaction;	2.9. Substrate specificity 2.9. Substrate specificitySubstrate specificity was determined by analyzing the puri-fied enzyme’s ability to hydrolyze various saccharides. Variouspolymeric saccharides (2.0%, w/v), including sucrose, 1-kestose,raffinose, inulin, levan, lactose, and maltose were used. Enzyme(50 μL, 3.0 g of protein) was added to 450 μL of substrate solution(pH 5.5). The reaction was conducted at 50C for 15 min. Reactionmixtures were heated at 100°C for 10 min to inactivate the enzyme.The amount of fructose or glucose released was determined byHPLC as described in Section 2.4. For the substrate specificity of thepurified enzyme, one unit of enzymatic activity was defined as theamount of enzyme required to produce 1 mol of fructose or glu-cose per min under the above reaction conditions. The enzymaticactivity toward sucrose was taken as 100%.

Reference： [1]Xu, Qiangsheng; Zheng, Xiaoqun; Huang, Meiping; Wu, Min; Yan, Yusi; Pan, Jiamao; Yang, Qi; Duan, Cheng-Jie; Liu, Jun-Liang; Feng, Jia-Xun [Process Biochemistry, 2015, vol. 50, # 8, p. 1237 - 1246]

37
[ 57-50-1 ]
[ 2280-44-6 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium dihydrogenphosphate; citric acid; In water; at 37℃; for 24h;pH 7.0;Microbiological reaction;Kinetics;	Transfructosylation reactions were carried out using uninduced,inulin-induced and sucrose-induced cells in a reaction volumeof 5 ml. The reaction mixture contained 100 mg lyophilizedcells and 10% (w/v) sucrose in 5 ml phosphate citrate buffer (pH7.0). The mixture was incubated at 37 C for 24 h at 220 rpm in areciprocating shaker (SI-300R Jeo Tech). At the end of the reaction,cells were separated out by centrifugation and the vials heated in aboiling water bath. The clear supernatant was analysed for residualsucrose, glucose and synthesized fructo-oligosaccharides

Reference： [1]Tetrahedron Asymmetry,2016,vol. 27,p. 1245 - 1252

38
[ 57-50-1 ]
[ 50-99-7 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Reference： [1]Journal of Biotechnology,2017,vol. 249,p. 25 - 33

39
[ 25101-98-8 ]
[ 470-69-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	With ammonia In methanol at 20℃;	General procedure for deacetylation of per-O-acetylated halodeoxy-1-kestose derivatives. General procedure: Solutions of per- O-acetylated halodeoxy-1-kestose derivatives (3-5, 0.05 g) in 3 mL dry methanol were treated with 1.5 mL saturated ammonia in methanol and stirred overnight at room temperature. The solvent was removed under reduced pressure and subjected to column chromatography on silica gel (pre-washed by methanol) by elution with methanol/chloroform (3:1). The method produced the corresponding halodeoxy-1-kestose derivatives 1, 6, and 7.1-Kestose3 (1, 0.034 g, 97%). 1H-NMR (500 MHz, D2O) δ: 5.37 (1H, d, J1,2 4.0 Hz, H-1), 4.22 (1H, d, J3′,4′ 8.6 Hz, H-3′), 4.13 (1H, d, J3′′,4′′ 8.6 Hz, H-3′′), 4.02 (1H, t, J3′′,4′′ 8.6 Hz, H-4′′), 3.98 (1H, t, J3′,4′ 8.6 Hz, H-4′), 3.83-3.80 (2H, m, H-5′, H-5′′), 3.79-3.71 (8H, m, H-1′a, H-5, H-6, H-6′, H-6′′), 3.70-3.60 (4H, m, H-3, H-1′b, H-1′′), 3.48 (1H, dd, J1,2 4.0 Hz, J2,3 9.7, H-2), 3.41 (1H, t, J3,4 9.7 Hz, H-4) ppm. 13C-NMR (125 MHz, D2O) δ: 104.2 (C-2′′), 103.7 (C-2′), 92.9 (C-1), 81.6 (C-5′), 81.5 (C-5′′), 77.0 (C-3′ & C-3′′), 74.9 (C-4′′), 74.2 (C-4′), 73.0 (C-3), 72.8 (C-5), 71.6 (C-2), 69.6 (C-4), 62.7 (C-6′′), 62.6 (C-6′), 61.3 (C-1′), 60.8 (C-1′′), 60.5 (C-6) ppm.
	With sodium methylate In methanol at 20℃;	3.4. Reduction Reaction General procedure: The purified acetylated FOSs were reduced by the following method [24]. The target compoundswere added to a round-bottom flask while dissolved in MeOH. NaOMe (2 g, 0.037 mol) was added in asingle portion and stirred at room temperature for 1 hour. After stirring for 20 min, the reactionwas neutralized with Dowex 50WX8 (H+ form) and then filtered. The resulting solution wasconcentrated under reduced pressure till thick oil was obtained. Purification by Sephadex LH-20column chromatography (eluting with methanol) afforded the target compounds as white powder.

Reference： [1]Tachrim, Zetryana Puteri; Nakamura, Tadashi; Sakihama, Yasuko; Hashidoko, Yasuyuki; Hashimoto, Makoto [Arkivoc, 2018, vol. 2018, # 7, p. 341 - 348]
[2]Duan, Wenjuan; Ji, Wenhua; Wei, Yuanan; Zhao, Ruixuan; Chen, Zijian; Geng, Yanling; Jing, Feng; Wang, Xiao [Molecules, 2018, vol. 23, # 2]

40
[ 470-69-9 ]
6,6′,6′′-tribromo-6,6′,6′′-trideoxy-1-kestose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; carbon tetrabromide; triphenylphosphine at 70℃; for 2h; Cooling with ice;	General procedure for Appel reaction: bromination. Solution of 1-kestose (1, 0.10 g, 0.198 mmol) in pyridine(2 mL) was cooled in an ice bath and treated with triphenylphosphine (0.47 g, 1.8 mmol, 9.1 equiv), followedby dropwise addition of a solution of carbon tetrabromide (0.30 g, 0.93 mmol, 4.7 equiv) in pyridine (0.93 mL).The reaction mixture was stirred at 70 °C for 2 h. After cooling the mixture in an ice bath, acetic anhydride (3mL, 32.0 mmol) and pyridine (2 mL) were added, and the mixture was stirred overnight at room temperature.The solvent was evaporated and the residue was partitioned between CH2Cl2 and water. The organic layer waswashed with 1 M HCl and brine, dried over MgSO4, reduced the solvent under high pressure and then purifiedby column chromatography on silica gel by elution with hexane/diethyl ether (1:6 and 1:10) to yield1′′,2,3,3′,3′′,4,4′,4′′-octa-O-acetyl-6,6′,6′′-tribromo-6,6′,6′′-trideoxy 1-kestose (4; 0.0516 g, 25%) as colorless amorphous mass.

Reference： [1]Tachrim, Zetryana Puteri; Nakamura, Tadashi; Sakihama, Yasuko; Hashidoko, Yasuyuki; Hashimoto, Makoto [Arkivoc, 2018, vol. 2018, # 7, p. 341 - 348]

41
[ 470-69-9 ]
6,6′,6′′-trichloro-6,6′,6′′-trideoxy-1-kestose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; tetrachloromethane; triphenylphosphine at 70℃; for 2h; Cooling with ice;	General procedure for Appel reaction: bromination. General procedure: Solution of 1-kestose (1, 0.10 g, 0.198 mmol) in pyridine(2 mL) was cooled in an ice bath and treated with triphenylphosphine (0.47 g, 1.8 mmol, 9.1 equiv), followedby dropwise addition of a solution of carbon tetrabromide (0.30 g, 0.93 mmol, 4.7 equiv) in pyridine (0.93 mL).The reaction mixture was stirred at 70 °C for 2 h. After cooling the mixture in an ice bath, acetic anhydride (3mL, 32.0 mmol) and pyridine (2 mL) were added, and the mixture was stirred overnight at room temperature.The solvent was evaporated and the residue was partitioned between CH2Cl2 and water. The organic layer waswashed with 1 M HCl and brine, dried over MgSO4, reduced the solvent under high pressure and then purifiedby column chromatography on silica gel by elution with hexane/diethyl ether (1:6 and 1:10) to yield1′′,2,3,3′,3′′,4,4′,4′′-octa-O-acetyl-6,6′,6′′-tribromo-6,6′,6′′-trideoxy 1-kestose (4; 0.0516 g, 25%) as colorless amorphous mass.

Reference： [1]Tachrim, Zetryana Puteri; Nakamura, Tadashi; Sakihama, Yasuko; Hashidoko, Yasuyuki; Hashimoto, Makoto [Arkivoc, 2018, vol. 2018, # 7, p. 341 - 348]

42
inulin [ No CAS ]
[ 57-48-7 ]
[ 59432-60-9 ]
[ 62512-19-0 ]
[ 470-69-9 ]
[ 13133-07-8 ]
[ 57-50-1 ]

Yield	Reaction Conditions	Operation in experiment
	With water; Bacillus sp. 11/3 inulinase polyacrylamide/polyethylene glycol composite immobilised In aq. acetate buffer at 40℃; for 24h; Enzymatic reaction;

Reference： [1]Temkov, Mishela; Dimitrovski, Darko; Velickova, Elena; Krastanov, Albert [Biocatalysis and Biotransformation, 2022, vol. 40, # 1, p. 50 - 63]

43
[ 57-50-1 ]
[ 57-48-7 ]
[ 50-99-7 ]
[ 138809-77-5 ]
[ 470-69-9 ]

Yield	Reaction Conditions	Operation in experiment
	With recombinant GH₆₈ levansucrase, N₈₄H/S₃₄₅A mutant In aq. buffer at 35℃; for 1h; Enzymatic reaction;	Late transfructosylation at 1 h and 24 h General procedure: For the qualitative analysis of the products of the transfructosylationof FFZm, LSZm, and their variants using 1.0 Msucrose, the reaction was performed at 35 C and pH 5.0 for upto 24 h in 30 mM sodium acetate buffer (pH 5.0). The[enzyme] was 0.03 μM (FFZm), 0.34 μM (LSZm), 0.13 μM(H79N-FFZm), 1.3 μM (A343S-FFZm), 0.64 μM (H79N/A343S-FFZm), 0.44 μM (H79N/L187F/A343S-FFZm),0.38 μM (N84H-LSZm), 0.24 μM (S345A-LSZm), or 0.26 μM(N84H/S345A-LSZm). At 1 and 24 h, a part of the reactionmixture was recovered, heated at 100 C for 3 min to terminatethe reaction, and diluted to 100-1 with 10 mM sorbitol ofinternal standard. The reaction products were analyzed byHPAEC-PAD. Resultant reaction samples at 1 h and 24 h wereanalyzed by methods A and B, respectively.For investigating the changes in the long LVO productionof LSZm, H79N/A343S-FFZm and H79N/L187F/A343SFFZm,we incubated each enzyme with different [sucrose]bearing 0.05, 0.1, 0.2, 0.4, 0.6, 0.8, or 1 M at 35 C and pH 5.0for 24 h in 40 mM sodium acetate buffer (pH 5.0), followedby heating at 100 C for 3 min. The reaction mixture wasdiluted with sorbitol solution and analyzed by HPAEC-PADusing method B. For the Fru-Man synthesis, the reaction of FFZm (2.2 μM),LSZm (16 μM), H79N-FFZm (2.4 μM), A343S-FFZm (5.8 μM),H79N/A343S-FFZm (9.3 μM), N84H-LSZm (2.7 μM), S345ALSZm(6.8 μM), or N84H/S345A-LSZm (2.6 μM) was performedwith 0.5 M sucrose and 1.0 M mannose at 35 C andpH 5.0 for 24 h, and was subsequently terminated by heating at100 C for 3 min. A sample for HPAEC-PAD analysis usingmethod A was prepared by 100-1-dilution of reaction mixturewith 10 mM sorbitol.

Reference： [1]Kikuchi, Asako; Kimura, Atsuo; Lang, Weeranuch; Okuyama, Masayuki; Sadahiro, Juri; Serizawa, Ryo; Tagami, Takayoshi; Tanuma, Masanari [Journal of Biological Chemistry, 2021, vol. 296]

44
[ 57-50-1 ]
[ 57-48-7 ]
[ 50-99-7 ]
[ 138809-77-5 ]
[ 470-69-9 ]
[ 562-68-5 ]

Yield	Reaction Conditions	Operation in experiment
	With recombinant GH₆₈ levansucrase In aq. buffer at 35℃; for 1h; Enzymatic reaction;	Late transfructosylation at 1 h and 24 h General procedure: For the qualitative analysis of the products of the transfructosylationof FFZm, LSZm, and their variants using 1.0 Msucrose, the reaction was performed at 35 C and pH 5.0 for upto 24 h in 30 mM sodium acetate buffer (pH 5.0). The[enzyme] was 0.03 μM (FFZm), 0.34 μM (LSZm), 0.13 μM(H79N-FFZm), 1.3 μM (A343S-FFZm), 0.64 μM (H79N/A343S-FFZm), 0.44 μM (H79N/L187F/A343S-FFZm),0.38 μM (N84H-LSZm), 0.24 μM (S345A-LSZm), or 0.26 μM(N84H/S345A-LSZm). At 1 and 24 h, a part of the reactionmixture was recovered, heated at 100 C for 3 min to terminatethe reaction, and diluted to 100-1 with 10 mM sorbitol ofinternal standard. The reaction products were analyzed byHPAEC-PAD. Resultant reaction samples at 1 h and 24 h wereanalyzed by methods A and B, respectively.For investigating the changes in the long LVO productionof LSZm, H79N/A343S-FFZm and H79N/L187F/A343SFFZm,we incubated each enzyme with different [sucrose]bearing 0.05, 0.1, 0.2, 0.4, 0.6, 0.8, or 1 M at 35 C and pH 5.0for 24 h in 40 mM sodium acetate buffer (pH 5.0), followedby heating at 100 C for 3 min. The reaction mixture wasdiluted with sorbitol solution and analyzed by HPAEC-PADusing method B. For the Fru-Man synthesis, the reaction of FFZm (2.2 μM),LSZm (16 μM), H79N-FFZm (2.4 μM), A343S-FFZm (5.8 μM),H79N/A343S-FFZm (9.3 μM), N84H-LSZm (2.7 μM), S345ALSZm(6.8 μM), or N84H/S345A-LSZm (2.6 μM) was performedwith 0.5 M sucrose and 1.0 M mannose at 35 C andpH 5.0 for 24 h, and was subsequently terminated by heating at100 C for 3 min. A sample for HPAEC-PAD analysis usingmethod A was prepared by 100-1-dilution of reaction mixturewith 10 mM sorbitol.

45
[ 57-50-1 ]
[ 57-48-7 ]
[ 50-99-7 ]
[ 138809-77-5 ]
[ 470-69-9 ]
[ 562-68-5 ]
[ 13133-07-8 ]

Yield	Reaction Conditions	Operation in experiment
	With recombinant GH₆₈ levansucrase, N₈₄H/S₃₄₅A mutant In aq. buffer at 35℃; for 24h; Enzymatic reaction;	Late transfructosylation at 1 h and 24 h General procedure: For the qualitative analysis of the products of the transfructosylationof FFZm, LSZm, and their variants using 1.0 Msucrose, the reaction was performed at 35 C and pH 5.0 for upto 24 h in 30 mM sodium acetate buffer (pH 5.0). The[enzyme] was 0.03 μM (FFZm), 0.34 μM (LSZm), 0.13 μM(H79N-FFZm), 1.3 μM (A343S-FFZm), 0.64 μM (H79N/A343S-FFZm), 0.44 μM (H79N/L187F/A343S-FFZm),0.38 μM (N84H-LSZm), 0.24 μM (S345A-LSZm), or 0.26 μM(N84H/S345A-LSZm). At 1 and 24 h, a part of the reactionmixture was recovered, heated at 100 C for 3 min to terminatethe reaction, and diluted to 100-1 with 10 mM sorbitol ofinternal standard. The reaction products were analyzed byHPAEC-PAD. Resultant reaction samples at 1 h and 24 h wereanalyzed by methods A and B, respectively.For investigating the changes in the long LVO productionof LSZm, H79N/A343S-FFZm and H79N/L187F/A343SFFZm,we incubated each enzyme with different [sucrose]bearing 0.05, 0.1, 0.2, 0.4, 0.6, 0.8, or 1 M at 35 C and pH 5.0for 24 h in 40 mM sodium acetate buffer (pH 5.0), followedby heating at 100 C for 3 min. The reaction mixture wasdiluted with sorbitol solution and analyzed by HPAEC-PADusing method B. For the Fru-Man synthesis, the reaction of FFZm (2.2 μM),LSZm (16 μM), H79N-FFZm (2.4 μM), A343S-FFZm (5.8 μM),H79N/A343S-FFZm (9.3 μM), N84H-LSZm (2.7 μM), S345ALSZm(6.8 μM), or N84H/S345A-LSZm (2.6 μM) was performedwith 0.5 M sucrose and 1.0 M mannose at 35 C andpH 5.0 for 24 h, and was subsequently terminated by heating at100 C for 3 min. A sample for HPAEC-PAD analysis usingmethod A was prepared by 100-1-dilution of reaction mixturewith 10 mM sorbitol.

46
[ 57-50-1 ]
[ 57-48-7 ]
[ 50-99-7 ]
[ 470-69-9 ]

Yield	Reaction Conditions	Operation in experiment
	With recombinant GH68 β-fructofuranosidase In aq. buffer at 35℃; for 24h; Enzymatic reaction;	Late transfructosylation at 1 h and 24 h General procedure: For the qualitative analysis of the products of the transfructosylationof FFZm, LSZm, and their variants using 1.0 Msucrose, the reaction was performed at 35 C and pH 5.0 for upto 24 h in 30 mM sodium acetate buffer (pH 5.0). The[enzyme] was 0.03 μM (FFZm), 0.34 μM (LSZm), 0.13 μM(H79N-FFZm), 1.3 μM (A343S-FFZm), 0.64 μM (H79N/A343S-FFZm), 0.44 μM (H79N/L187F/A343S-FFZm),0.38 μM (N84H-LSZm), 0.24 μM (S345A-LSZm), or 0.26 μM(N84H/S345A-LSZm). At 1 and 24 h, a part of the reactionmixture was recovered, heated at 100 C for 3 min to terminatethe reaction, and diluted to 100-1 with 10 mM sorbitol ofinternal standard. The reaction products were analyzed byHPAEC-PAD. Resultant reaction samples at 1 h and 24 h wereanalyzed by methods A and B, respectively.For investigating the changes in the long LVO productionof LSZm, H79N/A343S-FFZm and H79N/L187F/A343SFFZm,we incubated each enzyme with different [sucrose]bearing 0.05, 0.1, 0.2, 0.4, 0.6, 0.8, or 1 M at 35 C and pH 5.0for 24 h in 40 mM sodium acetate buffer (pH 5.0), followedby heating at 100 C for 3 min. The reaction mixture wasdiluted with sorbitol solution and analyzed by HPAEC-PADusing method B. For the Fru-Man synthesis, the reaction of FFZm (2.2 μM),LSZm (16 μM), H79N-FFZm (2.4 μM), A343S-FFZm (5.8 μM),H79N/A343S-FFZm (9.3 μM), N84H-LSZm (2.7 μM), S345ALSZm(6.8 μM), or N84H/S345A-LSZm (2.6 μM) was performedwith 0.5 M sucrose and 1.0 M mannose at 35 C andpH 5.0 for 24 h, and was subsequently terminated by heating at100 C for 3 min. A sample for HPAEC-PAD analysis usingmethod A was prepared by 100-1-dilution of reaction mixturewith 10 mM sorbitol.

47
[ 57-50-1 ]
[ 57-48-7 ]
[ 50-99-7 ]
[ 470-69-9 ]
[ 562-68-5 ]

Yield	Reaction Conditions	Operation in experiment
	With recombinant GH68 β-fructofuranosidase, H79N/A343S mutant In aq. buffer at 35℃; for 24h; Enzymatic reaction;	Late transfructosylation at 1 h and 24 h General procedure: For the qualitative analysis of the products of the transfructosylationof FFZm, LSZm, and their variants using 1.0 Msucrose, the reaction was performed at 35 C and pH 5.0 for upto 24 h in 30 mM sodium acetate buffer (pH 5.0). The[enzyme] was 0.03 μM (FFZm), 0.34 μM (LSZm), 0.13 μM(H79N-FFZm), 1.3 μM (A343S-FFZm), 0.64 μM (H79N/A343S-FFZm), 0.44 μM (H79N/L187F/A343S-FFZm),0.38 μM (N84H-LSZm), 0.24 μM (S345A-LSZm), or 0.26 μM(N84H/S345A-LSZm). At 1 and 24 h, a part of the reactionmixture was recovered, heated at 100 C for 3 min to terminatethe reaction, and diluted to 100-1 with 10 mM sorbitol ofinternal standard. The reaction products were analyzed byHPAEC-PAD. Resultant reaction samples at 1 h and 24 h wereanalyzed by methods A and B, respectively.For investigating the changes in the long LVO productionof LSZm, H79N/A343S-FFZm and H79N/L187F/A343SFFZm,we incubated each enzyme with different [sucrose]bearing 0.05, 0.1, 0.2, 0.4, 0.6, 0.8, or 1 M at 35 C and pH 5.0for 24 h in 40 mM sodium acetate buffer (pH 5.0), followedby heating at 100 C for 3 min. The reaction mixture wasdiluted with sorbitol solution and analyzed by HPAEC-PADusing method B. For the Fru-Man synthesis, the reaction of FFZm (2.2 μM),LSZm (16 μM), H79N-FFZm (2.4 μM), A343S-FFZm (5.8 μM),H79N/A343S-FFZm (9.3 μM), N84H-LSZm (2.7 μM), S345ALSZm(6.8 μM), or N84H/S345A-LSZm (2.6 μM) was performedwith 0.5 M sucrose and 1.0 M mannose at 35 C andpH 5.0 for 24 h, and was subsequently terminated by heating at100 C for 3 min. A sample for HPAEC-PAD analysis usingmethod A was prepared by 100-1-dilution of reaction mixturewith 10 mM sorbitol.

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 470-69-9 ] {[proInfo.proName]}

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[ 470-69-9 ] Synthesis Path-Upstream 1~11

[ 470-69-9 ] Synthesis Path-Downstream 1~47

Precautionary Statements-General

Prevention

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Physical hazards

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