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[ CAS No. 50-99-7 ] {[proInfo.proName]}

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Chemical Structure| 50-99-7
Chemical Structure| 50-99-7
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Product Details of [ 50-99-7 ]

CAS No. :50-99-7 MDL No. :MFCD00148912
Formula : C6H12O6 Boiling Point : -
Linear Structure Formula :- InChI Key :GZCGUPFRVQAUEE-SLPGGIOYSA-N
M.W : 180.16 Pubchem ID :107526
Synonyms :
Glucose;Dextrose;NSC 287045;D-(+)-Glucose
Chemical Name :(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanal

Calculated chemistry of [ 50-99-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 5
Num. H-bond acceptors : 6.0
Num. H-bond donors : 5.0
Molar Refractivity : 36.97
TPSA : 118.22 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -9.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : -0.47
Log Po/w (XLOGP3) : -2.94
Log Po/w (WLOGP) : -3.38
Log Po/w (MLOGP) : -2.91
Log Po/w (SILICOS-IT) : -1.6
Consensus Log Po/w : -2.26

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 1.23
Solubility : 3030.0 mg/ml ; 16.8 mol/l
Class : Highly soluble
Log S (Ali) : 1.02
Solubility : 1870.0 mg/ml ; 10.4 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 2.45
Solubility : 50500.0 mg/ml ; 281.0 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.31

Safety of [ 50-99-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 50-99-7 ]

* 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.

  • Downstream synthetic route of [ 50-99-7 ]

[ 50-99-7 ] Synthesis Path-Downstream   1~94

  • 1
  • [ 2434-56-2 ]
  • [ 50-99-7 ]
  • D-glucose-(6-amino-pyrimidin-4-ylimine) [ No CAS ]
  • 2
  • [ 94-25-7 ]
  • [ 50-99-7 ]
  • [ 28318-85-6 ]
  • 4
  • [ 50-99-7 ]
  • [ 20691-72-9 ]
  • D-glucose-(4-iodo-2-nitro-phenylimine) [ No CAS ]
  • 7
  • [ 50-99-7 ]
  • [ 14685-90-6 ]
  • D-<i>arabino</i>-[2]hexosulose-bis-(4-ethoxycarbonyl-phenylhydrazone) [ No CAS ]
  • 9
  • [ 50-99-7 ]
  • [ 7211-54-3 ]
  • [ 93284-19-6 ]
  • 10
  • [ 2469-99-0 ]
  • [ 50-99-7 ]
  • [ 81661-23-6 ]
  • 11
  • [ 50-99-7 ]
  • [ 471-53-4 ]
  • 30-O-(β-D-glucopyranosyl)18β-glycyrrhetinic acid [ No CAS ]
  • 30-O-(6-O-malonyl-β-D-glucopyranosyl)18β-glycyrrhetinic acid [ No CAS ]
  • 3-O-<β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl>18β-glycyrrhetinic acid [ No CAS ]
  • 30-O-<β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl>18β-glycyrrhetinic acid [ No CAS ]
  • 12
  • [ 50-99-7 ]
  • [ 471-53-4 ]
  • 30-O-(β-D-glucopyranosyl)18β-glycyrrhetinic acid [ No CAS ]
  • 30-O-(6-O-malonyl-β-D-glucopyranosyl)18β-glycyrrhetinic acid [ No CAS ]
  • 3-O-<β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl>18β-glycyrrhetinic acid [ No CAS ]
  • 3-O-<6-O-malonyl-β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl>18β-glycyrrhetinic acid [ No CAS ]
  • 13
  • [ 50-99-7 ]
  • [ 471-53-4 ]
  • 30-O-(β-D-glucopyranosyl)18β-glycyrrhetinic acid [ No CAS ]
  • 3-O-<β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl>18β-glycyrrhetinic acid [ No CAS ]
  • 30-O-<β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl>18β-glycyrrhetinic acid [ No CAS ]
  • 3-O-<β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl>-30-O-(β-D-glucopyranosyl)18β-glycyrrhetinic acid [ No CAS ]
  • 14
  • [ 50-99-7 ]
  • [ 453-17-8 ]
  • [ 10323-20-3 ]
  • [ 583-50-6 ]
  • 16
  • [ 50-99-7 ]
  • [ 100-52-7 ]
  • [ 3006-41-5 ]
  • [ 86833-15-0 ]
  • [ 86833-16-1 ]
  • 17
  • [ 27297-45-6 ]
  • [ 50-99-7 ]
  • [ 480-18-2 ]
  • 18
  • [ 50-99-7 ]
  • [ 123-31-9 ]
  • [ 497-76-7 ]
  • [ 497-76-7 ]
  • 19
  • [ 50-99-7 ]
  • [ 56-40-6 ]
  • [ 67-47-0 ]
  • [ 3658-77-3 ]
  • [ 1073-96-7 ]
  • [ 3857-25-8 ]
  • 20
  • (R)-3,5,7-Trihydroxy-2-[4-hydroxy-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-chroman-4-one [ No CAS ]
  • [ 50-99-7 ]
  • [ 480-18-2 ]
  • [ 480-18-2 ]
  • 22
  • [ 50-99-7 ]
  • [ 123-31-9 ]
  • emulsin [ No CAS ]
  • [ 497-76-7 ]
  • 23
  • [ 50-99-7 ]
  • [ 17678-20-5 ]
  • [ 3658-77-3 ]
  • [ 28564-83-2 ]
  • 24
  • [ 50-99-7 ]
  • [ 147-85-3 ]
  • [ 3658-77-3 ]
  • [ 25343-57-1 ]
  • [ 135596-33-7 ]
  • [ 85213-22-5 ]
  • 26
  • [ 67-56-1 ]
  • [ 50-99-7 ]
  • [ 6665-86-7 ]
  • flavone 7-O-β-D-(4'-O-methyl)-glucopyranoside [ No CAS ]
  • 4'-hydroxyflavone 7-O-β-D-4-O-methylglucopyranoside [ No CAS ]
  • 27
  • [ 50-99-7 ]
  • [ 1125-88-8 ]
  • [ 3006-41-5 ]
  • 28
  • [ 50-99-7 ]
  • [ 7512-17-6 ]
  • [ 131-48-6 ]
  • 29
  • [ 50-99-7 ]
  • [ 7512-17-6 ]
  • [ 63-37-6 ]
  • [ 3063-71-6 ]
  • 30
  • [ 486-25-9 ]
  • [ 50-99-7 ]
  • [ 1435-71-8 ]
  • [ 2440-22-4 ]
  • [ 54659-85-7 ]
YieldReaction ConditionsOperation in experiment
92.1% With sodium hydroxide; In methanol; water; EXAMPLE 16 A mixture of methanol 60 ml, water 30 ml, 97% sodium hydroxide 12.4 g and 2-nitro-2'-hydroxy-5'-methylazobenzene 12.9 g was heated and stirred at 45~50 C. 9-fluorenone 1.0 g and then glucose 5.5 g were added to the resultant mixture over 30 minutes while stirring. The mixture was further stirred at 75 C. (boiling point) for 7 hours. As this result, the azobenzene disappeared to produce 2-(2'-hydroxy-5'-methylphenyl)benzotriazole-N-oxide. Water 50 ml was added to the reaction liquor thus obtained, and the liquor was neutralized with 62% sulfuric acid 19 g to precipitate a crystal. The crystal thus obtained was separated by filtration, and the separated crystal was fully washed with water and further with methanol. The crystal thus washed was dried to produce 11.1 g of 2-(2'-hydroxy-5'-methylphenyl)benzotriazole having a melting point of 138 to 140 C. at the yield of 92.1%.
92.1% With sodium hydroxide; In methanol; water; Example 16 A mixture of methanol (60 ml), water (30 ml), 97% sodium hydroxide (12.4 g) and 2-nitro-2'-hydroxy-5'-methyl azobenzene (12.9 g) was heated and stirred at 45~50C. 9-fluorenone (1.0 g) and then glucose (5.5 g) were added to the resultant mixture over 30 minutes while stirring. The mixture was further stirred at 75C (boiling point) for 7 hours. As a result, the azobenzene disappeared to produce 2-(2'-hydroxy-5'-methylphenyl)benzotriazole-N-oxide. Water (50 ml) was added to the reaction liquor thus obtained, and the liquor was neutralized with 62 % sulfuric acid (19 g) to precipitate a crystal. The crystal thus obtained was separated by filtration, and the separated crystal was fully washed with water and further with methanol. The crystal thus washed was dried to produce 11.1 g of 2-(2'-hydroxy-5'-methylphenyl)benzotriazole having a melting point of 138 to 140C at the yield of 92.1 %.
  • 31
  • [ 921-01-7 ]
  • [ 50-99-7 ]
  • [ 10318-18-0 ]
  • [ 565157-43-9 ]
YieldReaction ConditionsOperation in experiment
With pyridine; In methanol; water; Example 2 Synthesis of 2-(1,2,3,4,5-pentahydroxypentyl)thiazolidine-4-carboxylic acid 17.56 Grams (100 mmol) of cysteine hydrochloride and 18.02 g (100 mmol) of glucose were dissolved in 35 ml of pure water, 8.36 ml (100 mmol) of pyridine was then added thereto, and the resulting solution was stirred at room temperature for 96 hours. 200 Milliliters of methanol was added to the stirred solution, whereby a precipitate was formed. The precipitate was collected by filtering and was suspended in 300 ml of water. The suspension was heated to 50ØC to give a solution. The solution was condensed to about 100 ml at 45ØC under reduced pressure. The insoluble matters were removed by filtration, and the remaining solution was, after added with 200 ml of methanol, left to stand in a refrigerator overnight. The resulting crystals were collected by filtration and dried under reduced pressure, whereby 15.0 g of a white powder was obtained (molar yield based on the cysteine: 52.9 %). The white powder was identified as the target compound since the ion mass number of the white powder by ESI-MS spectrum (Electron Spray Ionization-Mass Spectrometry) was, as is shown in Fig. 2 given later, equal to the molecular weight (284) of the compound obtained by hydrogenating the target compound.
  • 32
  • [ 118525-40-9 ]
  • [ 113558-15-9 ]
  • [ 56725-99-6 ]
  • [ 50-99-7 ]
YieldReaction ConditionsOperation in experiment
With methanol; In chloroform;Column chromatography;Purification / work up; 20 g of the extraction prepared by enzyme hydrolysis was purified by silica gel column chromatography, charged with silica gel 10Og. Here, chloroform and methanol were used as the eluting solvents. Fractions were obtained by increasing the ratio of chloroform and methanol from 10:1 to 2:1 and 1.8 g of icariside I was produced therefrom. The resulting product was identified (Varian Gemini 2000 300MHz, Varian) and shows the following features.< Physical and chemical properties of icariside I > Morphology: pale yellow micro-crystalPositive FAB-MS: 531[M+H]1R NMR: (DMSO-d6) delta: 1.70, 1.83(ea. 3H, s, Me-4",5"), 2.90(2H, Hl"), 3.87(3H, s, OMe), 3.83-5.40(m, sugar protons), 6.64(1H, s, H6), 7.16(2H, d, 9, H3',5'), 8.23(2H, d, 9, H2',6'). 13C-NMR: (DMSO-d6) delta: 146.9, 136.2, 176.5, 160.1, 97.5, 160.6,108.1 152.7, 104.5, 123.4, 129.3, 114.1, 158.5, 114.1, 129.3, 21.5, 122.3, 131.1, 25.4, 17.9, 100.5, 73.4, 76.7, 69.7, 77.2, 60.7, 55.4.Acid hydroly sates: <strong>[118525-40-9]icaritin</strong>, glucose
  • 33
  • [ 69-79-4 ]
  • [ 3371-50-4 ]
  • [ 7485-51-0 ]
  • [ 50-99-7 ]
  • [ 35997-20-7 ]
  • [ 499-40-1 ]
  • 34
  • [ 50-99-7 ]
  • [ 13515-95-2 ]
  • C13H26N2O8 [ No CAS ]
  • 36
  • fucoidan [ No CAS ]
  • [ 58-86-6 ]
  • [ 3458-28-4 ]
  • [ 2438-80-4 ]
  • [ 50-99-7 ]
  • [ 59-23-4 ]
  • 37
  • [ 50-99-7 ]
  • [ 67-03-8 ]
  • C18H27N4O6S(1+)*Cl(1-) [ No CAS ]
  • 38
  • [ 1160434-47-8 ]
  • [ 50-99-7 ]
  • [ 480-41-1 ]
  • 39
  • [ 50-99-7 ]
  • [ 64017-81-8 ]
  • N-(D-glucopyranosyl)-3'-aminopropionamide [ No CAS ]
  • 40
  • [ 50-99-7 ]
  • [ 64017-81-8 ]
  • N-(1-deoxy-D-fructos-1-yl)-3'-aminopropionamide [ No CAS ]
  • 42
  • fucoidan [ No CAS ]
  • [ 58-86-6 ]
  • [ 3458-28-4 ]
  • [ 2438-80-4 ]
  • [ 50-99-7 ]
  • [ 59-23-4 ]
  • [ 70332-45-5 ]
  • 43
  • [ 69-79-4 ]
  • [ 1109-28-0 ]
  • [ 3371-50-4 ]
  • [ 7485-51-0 ]
  • [ 99-20-7 ]
  • [ 50-99-7 ]
  • [ 499-40-1 ]
YieldReaction ConditionsOperation in experiment
In water; at 40℃;pH 6.0;Acetate buffer; Enzymatic reaction;Reactivity; Experiment 12-1Product from Maltose by the Enzyme ReactionAqueous maltose solution and acetate buffer (pH 6.0) were mixed to give final concentrations of 1percent (w/v) and 10 mM, respectively, to make into a substrate solution. The substrate solution was admixed with 10 units/g-solid substrate of alpha-glucosyltransferase, obtained by the method in Experiment 6, and followed by the enzyme reaction at 40° C. and pH 6.0. Aliquots were sampled from the reaction mixture with time and the reaction was stopped by keeping at 100° C. for 10 min. The saccharide compositions of the samples were measured by HPLC and GC. HPLC and GC were carried out under the conditions described in Experiment 4-2. The results are in Table 10. TABLE 10 Reaction Saccharide Composition (percent, w/w) Time DP1 DP2 DP3 (hr) Glucose Maltose Isomaltose Neotrehalose Maltotriose Panose Isopanose Isomaltotriose DP4 DP5 DP6 0 0.0 99.2 0.0 0.0 0.8 0.0 0.0 0.0 0.0 0.0 0.0 1 12.1 55.0 0.7 0.0 13.2 16.1 0.0 0.0 2.9 0.0 0.0 2 18.4 33.5 1.0 0.0 14.4 24.1 0.0 0.0 7.6 1.0 0.0 4 23.7 17.3 2.5 0.0 10.0 29.3 0.0 0.0 13.0 4.2 0.0 8 27.0 10.4 4.7 0.0 4.9 27.8 0.0 0.0 15.9 5.3 4.0 24 30.4 6.0 10.0 2.6 1.4 11.0 1.0 3.6 15.3 10.2 8.5 48 31.5 6.2 13.8 3.9 0.7 4.1 1.5 4.2 12.4 10.3 11.4 DP: Glucose polymerization degreeAs is evident from the results in Table 10, at initial stage (after one hour) of the reaction, glucose, maltotriose, and panose were formed as major reaction products from the substrate, maltose, by the action of the alpha-glucosyltransferase of the present invention. Also, oligosaccharides with a glucose polymerization degree of 4 and 5 were formed when the reaction time was elapsed 2 to 4 hours. Accompanying with the progress of the reaction, the content of maltotriose reached a maximum, 14.4percent, at 2 hours and then decreased; and the content of panose reached a maximum, 29.3percent at 4 hours and then decreased; and the content of isomaltose was increased with the decrease of the contents of maltotriose and panose. Further, the contents of isomaltose and oligosaccharides with a glucose polymerization degree of 4 or higher were increased until 48 hours.From these results, it was revealed that the alpha-glucosyltransferase of the present invention acts on maltose and forms glucose, maltotriose, and panose by catalyzing both alpha-1,4 and alpha-1,6 glucosyl transfer at initial stage of the reaction; and forms isomaltose, which is formed by alpha-1,6 glucosyl transfer to glucose, and isopanose and isomaltotriose, which are formed by alpha-1,4 and alpha-1,6 glucosyl transfer to isomaltose accompanied with the progress of the reaction. Since the identification of many kinds of oligosaccharide with glucose polymerization degree of 4 or higher is difficult in this experiment, the reaction mechanism of the enzyme was investigated in the following Experiment 12-2 using maltopentaose, whose glucose polymerization degree is higher than maltose, as substrate.
  • 44
  • [ 56-87-1 ]
  • [ 50-99-7 ]
  • [ 290-37-9 ]
  • [ 109-08-0 ]
  • [ 123-32-0 ]
  • [ 5910-89-4 ]
  • [ 22047-25-2 ]
  • [ 13360-65-1 ]
  • [ 108-50-9 ]
  • [ 14667-55-1 ]
  • [ 13925-07-0 ]
  • [ 13360-64-0 ]
  • 45
  • [ 50-99-7 ]
  • [ 1197040-29-1 ]
  • [ 14401-51-5 ]
  • 2-(4-chlorophenyl)-5-(1,2-dihydroxyethyl)-4-phenyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-b]pyridine-6,7-diol [ No CAS ]
  • 46
  • [ 50-99-7 ]
  • [ 1197040-29-1 ]
  • [ 14401-51-5 ]
  • C20H22ClN3O5 [ No CAS ]
  • 47
  • [ 50-99-7 ]
  • [ 88333-03-3 ]
  • [ 14401-51-5 ]
  • 4-benzyl-2-(4-chlorophenyl)-5-(1,2-dihydroxyethyl)-4,5,6,7-tetrahydro-3H-imidazo[4,5-b]pyridine-6,7-diol [ No CAS ]
  • 48
  • [ 50-99-7 ]
  • [ 88333-03-3 ]
  • [ 14401-51-5 ]
  • C21H24ClN3O5 [ No CAS ]
  • 50
  • 3-O-[β-D-xylopyranosyl-(1->2)-β-D-fucopyranosyl-(1->6)-2-(acetamido)-2-deoxy-β-D-glucopyranosyl]-21-O-{(2E,6S)-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-β-D-quinovopyranosyl}-2,6-dimethylocta-2,7-dienoyl}acacic acid 28-O-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranosyl ester [ No CAS ]
  • [ 58-86-6 ]
  • [ 7658-08-4 ]
  • [ 3615-37-0 ]
  • [ 3615-41-6 ]
  • [ 50-99-7 ]
  • [ 7512-17-6 ]
  • 51
  • Dictyopteris polypodioides fucoidan [ No CAS ]
  • [ 58-86-6 ]
  • [ 3458-28-4 ]
  • [ 2438-80-4 ]
  • [ 3615-41-6 ]
  • [ 50-99-7 ]
  • [ 59-23-4 ]
  • 52
  • Sargassum sp. fucoidan [ No CAS ]
  • [ 58-86-6 ]
  • [ 3458-28-4 ]
  • [ 2438-80-4 ]
  • [ 3615-41-6 ]
  • [ 50-99-7 ]
  • [ 59-23-4 ]
  • 54
  • Salmonella enterica O51 O-polysaccharide [ No CAS ]
  • [ 50-99-7 ]
  • [ 59-23-4 ]
  • [ 7512-17-6 ]
  • [ 134-61-2 ]
  • 55
  • [ 64-17-5 ]
  • [ 50-99-7 ]
  • [ 3198-49-0 ]
  • 56
  • [ 64-17-5 ]
  • [ 50-99-7 ]
  • [ 3198-49-0 ]
  • [ 539-88-8 ]
YieldReaction ConditionsOperation in experiment
at 20℃;pH 7.4;aq. phosphate buffer;Kinetics; General procedure: All reagents were purchased from Aldrich and Frontier Scientific. For thermodynamic binding experiments, an RF-1501 Shimadzu fluorometer was used. For stopped-flow experiments, an Applied Photophysics RX2000 Rapid Mixing stopped-flow unit with FluoromaxIIII fluorometer (Horiba) was used. The dead time for this instrument is 0.05 s. All kinetic experiments were conducted in phosphate buffer (0.1 M) at pH 7.4 and at room temperature. Kinetic measurements were performed under pseudo first-order conditions. In a fixed concentration of IQBAs, different concentrations of sugars were mixed within a short time period. All the reaction curves were fitted using formula (1) in Origin 8. Using formula (2), Kobs can be calculated. Values for kon and koff were calculated using formula (3) by varying [S], the substrate concentration.
YieldReaction ConditionsOperation in experiment
at 20℃;pH 7.4;aq. phosphate buffer;Kinetics; General procedure: All reagents were purchased from Aldrich and Frontier Scientific. For thermodynamic binding experiments, an RF-1501 Shimadzu fluorometer was used. For stopped-flow experiments, an Applied Photophysics RX2000 Rapid Mixing stopped-flow unit with FluoromaxIIII fluorometer (Horiba) was used. The dead time for this instrument is 0.05 s. All kinetic experiments were conducted in phosphate buffer (0.1 M) at pH 7.4 and at room temperature. Kinetic measurements were performed under pseudo first-order conditions. In a fixed concentration of IQBAs, different concentrations of sugars were mixed within a short time period. All the reaction curves were fitted using formula (1) in Origin 8. Using formula (2), Kobs can be calculated. Values for kon and koff were calculated using formula (3) by varying [S], the substrate concentration.
YieldReaction ConditionsOperation in experiment
at 20℃;pH 7.4;aq. phosphate buffer;Kinetics; General procedure: All reagents were purchased from Aldrich and Frontier Scientific. For thermodynamic binding experiments, an RF-1501 Shimadzu fluorometer was used. For stopped-flow experiments, an Applied Photophysics RX2000 Rapid Mixing stopped-flow unit with FluoromaxIIII fluorometer (Horiba) was used. The dead time for this instrument is 0.05 s. All kinetic experiments were conducted in phosphate buffer (0.1 M) at pH 7.4 and at room temperature. Kinetic measurements were performed under pseudo first-order conditions. In a fixed concentration of IQBAs, different concentrations of sugars were mixed within a short time period. All the reaction curves were fitted using formula (1) in Origin 8. Using formula (2), Kobs can be calculated. Values for kon and koff were calculated using formula (3) by varying [S], the substrate concentration.
  • 60
  • [ 497-76-7 ]
  • [ 50-99-7 ]
  • [ 123-31-9 ]
  • 61
  • [ 63-42-3 ]
  • [ 584-30-5 ]
  • [ 584-30-5 ]
  • [ 536-11-8 ]
  • [ 536-11-8 ]
  • [ 157240-67-0 ]
  • [ 490-40-4 ]
  • [ 50-99-7 ]
  • [ 59-23-4 ]
  • 62
  • [ 1391144-84-5 ]
  • [ 50-99-7 ]
  • [ 59-23-4 ]
  • [ 569-92-6 ]
  • 63
  • heteropolysaccharide HPS4-2A from Radix Hedysari [ No CAS ]
  • [ 5328-37-0 ]
  • [ 3615-41-6 ]
  • [ 50-99-7 ]
  • [ 59-23-4 ]
  • [ 134-61-2 ]
YieldReaction ConditionsOperation in experiment
With water; trifluoroacetic acid; at 121℃; for 3.5h; The compositional analysis of HPS4-2A was performed by the alditol acetate method [16], with minor modifications. Briefly, HPS4-2A was hydrolyzed by 2M trifluoroacetic acid at 121°C for 3.5 h followed by reduction in distilled water with NaBD4 1.5 h at room temperature, and subsequent acetylation by acetic anhydride with pyridine as the catalyst at 100°C for 1h. The standards, including rhamnose, arabinose, xylose, mannose, glucose, galactose, 2-acetamido-2-deoxy-d-galactose, treated in parallel with sample.
  • 64
  • polysaccharide from Artemisia argyi, MW 5169 Da [ No CAS ]
  • [ 58-86-6 ]
  • [ 3458-28-4 ]
  • [ 10323-20-3 ]
  • [ 50-69-1 ]
  • [ 634-74-2 ]
  • [ 50-99-7 ]
  • [ 59-23-4 ]
  • [ 7512-17-6 ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid; In water; at 100℃; for 8h;Sealed tube; A simple and sensitive high performance liquid chromatographic method was applied to the simultaneous determination of nine kinds of monosaccharides (glucose, rhamnose, mannose, arabinose, galactose, xylose, ribose, galacturonic acid and N-acetyl-d-glucosamine) in FAAP-02 by pre-column derivatization with 1-phenyl-3-5-pyrazolone (PMP) as described previously with proper modification (Lv et al., 2009). In brief, FAAP-02 was hydrolyzed with TFA (3M) for 8h at 100C in a sealed ampoule. After cooling to room temperature, the reaction mixture was centrifuged and the supernatant was collected and lyophilized. The hydrolyzed sample or monosaccharide standard aqueous solution was mixed with aqueous NaOH (0.25M) and PMP methanol solution (0.25M) thoroughly. Then each mixture was incubated at 70C for 90min. After cooled and neutralized with HCl (0.25M), the resulting solution was extracted with chloroform to remove the excess reagents. The aqueous layer was filtered through a 0.45mum membrane before detection. The analysis of PMP-labeled monosaccharides was performed on an Agilent 1260 HPLC system equipped with a ZORBAX Eclipse XDB-C18 (250mm×4.6mm, id: 5mum, column temperature: 30C). The wavelength of detection was 250nm. Elution was carried out with a mixture of acetonitrile and phosphate buffer (0.06M, pH 6.8) in a ratio of 17: 83 (v/v, %) at a flow rate of 1mL/min.
  • 65
  • [ 1500092-25-0 ]
  • [ 50-69-1 ]
  • [ 24259-59-4 ]
  • [ 50-99-7 ]
  • [ 921-60-8 ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid; In water; at 120℃; for 4h; Compound 1 (about 4 mg) was added into a solution of water (1 mL) and 2N aqueous CF3COOH(2 mL), heated to 120°C under reflux conditions for 4 h. The mixture was diluted with water (2 mL) and then extracted with EtOAc (3 £2 mL). The combined organic phase was washed with brine and evaporated to dryness to afford the aglycones. The aqueous phase was concentrated. Then dry pyridine (1 mL) and L-cysteine methyl ester hydrochloride (2 mg) were added into the residue. Each mixture was reacted at 60°C for 1 h, and 0.5mL of (trimethylsilyl) imidazole dissolved in H2O was added, followed by heating to dryness at 60°C for 2 h. Each dried reactant was extracted with n-hexane (3 £ 1 mL) and H2O (1 mL, each). The n-hexane fraction was subjected to GC (column: Rtx-1, 0.25mm i.d. 0.25 mm, length 30 m). The conditions of GC were flame ionization detector; column temperature 100?180°C (10°C min?1)and 180?230°C (3°C min21); injector temperature 250°C; detector temperature 300°C and the carrier gas (N2, 0.8mLmin21). Under these conditions, these sugars of each reactants were identified by comparison with authentic samples: tR (min) 7.56 (D-ribose), 7.85 (L-ribose), 10.49 (D-glucose) and 11.10 (L-glucose).
  • 66
  • [ 1558054-12-8 ]
  • [ 2438-80-4 ]
  • [ 50-99-7 ]
  • [ 59-23-4 ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid; at 90℃; for 3h; General procedure: Compounds 1 and 2 (3 mg) were, respectively, added to trifluoroacetic acid (4 N) solution (6 ml), then heated for 3 h under 908C. After cooled to room temperature, the hydrolytical solution was extracted with chloroform (3 £ 6.0 ml). The water layer was concentrated to 0.5 ml. The completely concentrated water layer and reference substances of b-D-glucose, b-Dgalactose, and a-L-rhamnose were derived by reacting with 1.5 mg hydroxylamine hydrochloride and 0.5 ml pyridine for 1 h at 908C. After cooling, 0.9 ml Ac2O was added and the mixture was heated at 908C for 1 h. The reaction mixtures were evaporated under reduced pressure, and the resulting aldononitrile peracetates were analyzed by GC-MS. The samples (10 ml) were injected into a HP-1 30m £ 0.2mm chromatographic column (Agilent). The injector temperature was 280C. The helium carrier gas flow was maintained at 1 ml/min. The oven temperature program was as follows: 100C for 2 min, 2008Cat 208C/min (remaining at 2008C for 2 min), then to 260Cat 10C/min (remaining at 3008C for 3min)- the total run time was 18 min. The range of MS was m/z 30-500. The tR values of b-D-glucose, b-D-galactose, and a-Lrhamnose derivatives were 11.05, 11.26, and 8.86 min, respectively.
  • 67
  • [ 1558054-13-9 ]
  • [ 2438-80-4 ]
  • [ 50-99-7 ]
  • [ 59-23-4 ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid; at 90℃; for 3h; General procedure: Compounds 1 and 2 (3 mg) were, respectively, added to trifluoroacetic acid (4 N) solution (6 ml), then heated for 3 h under 908C. After cooled to room temperature, the hydrolytical solution was extracted with chloroform (3 £ 6.0 ml). The water layer was concentrated to 0.5 ml. The completely concentrated water layer and reference substances of b-D-glucose, b-Dgalactose, and a-L-rhamnose were derived by reacting with 1.5 mg hydroxylamine hydrochloride and 0.5 ml pyridine for 1 h at 908C. After cooling, 0.9 ml Ac2O was added and the mixture was heated at 908C for 1 h. The reaction mixtures were evaporated under reduced pressure, and the resulting aldononitrile peracetates were analyzed by GC-MS. The samples (10 ml) were injected into a HP-1 30m £ 0.2mm chromatographic column (Agilent). The injector temperature was 280C. The helium carrier gas flow was maintained at 1 ml/min. The oven temperature program was as follows: 100C for 2 min, 2008Cat 208C/min (remaining at 2008C for 2 min), then to 260Cat 10C/min (remaining at 3008C for 3min)- the total run time was 18 min. The range of MS was m/z 30-500. The tR values of b-D-glucose, b-D-galactose, and a-Lrhamnose derivatives were 11.05, 11.26, and 8.86 min, respectively.
  • 68
  • quercetin-4'-methoxy 3-O-di-(L-rhamnopyranosyl)-(1'''→2",1''''→6")-β-D-glucopyranoside [ No CAS ]
  • [ 3615-41-6 ]
  • [ 50-99-7 ]
  • [ 520-34-3 ]
  • 69
  • difucosyllactose [ No CAS ]
  • [ 2438-80-4 ]
  • [ 50-99-7 ]
  • [ 59-23-4 ]
  • [ 5965-66-2 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; In water; at 50℃; for 96h; Example 3 - Selective hydrolysis of DFL with acids. DFL (50 mg) was dissolved in water (0.5 ml) and treated with add under the conditions ndicated in the table below. Samples were analysed by HPLC using CAD detection.
  • 70
  • 4'-O-methylluteolin-7-O-β-[6-O-β-xylopyranosylglucopyranoside] [ No CAS ]
  • [ 50-99-7 ]
  • [ 520-34-3 ]
  • 71
  • [ 50-99-7 ]
  • [ 6338-41-6 ]
  • [ 3238-40-2 ]
  • 72
  • [ 56-87-1 ]
  • [ 50-99-7 ]
  • [ 109-08-0 ]
  • [ 5910-89-4 ]
  • [ 13925-00-3 ]
  • [ 13360-65-1 ]
  • [ 15707-23-0 ]
  • 73
  • heteroglycan from Termitomyces clypeatus [ No CAS ]
  • [ 3458-28-4 ]
  • [ 2438-80-4 ]
  • [ 50-99-7 ]
  • [ 59-23-4 ]
  • 74
  • [ 63-42-3 ]
  • [ 121153-20-6 ]
  • [ 50-99-7 ]
  • [ 59-23-4 ]
  • 75
  • 3-hydroxypropylamine hydrochloride [ No CAS ]
  • [ 63-42-3 ]
  • [ 121153-20-6 ]
  • [ 50-99-7 ]
  • [ 59-23-4 ]
  • [ 201667-53-0 ]
  • 76
  • [ 58846-77-8 ]
  • [ 50-99-7 ]
  • [ 112-30-1 ]
  • 77
  • 1-O-[(3β)-28-oxo-3-[β-D-xylopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→6)-2-acetamido-2-deoxy-β-D-glucopyranosyl]oxy}olean-12-en-28-yl]-β-D-glucopyranose [ No CAS ]
  • [ 58-86-6 ]
  • [ 5328-37-0 ]
  • [ 50-99-7 ]
  • [ 7512-17-6 ]
  • 78
  • 3β,20α,24-trihydroxy-29-norolean-12-en-28-oic acid 24-O-β-L-fucopyranosyl-(1→2)-β-D-glucopyranoside [ No CAS ]
  • [ 2438-80-4 ]
  • [ 50-99-7 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; In methanol; at 90℃; for 7h; General procedure: The operation was carried out with a modified method reported.8,16 In brief, the solution of sample (each about 4.0mg) is homogenized in methanol (2.5mL), associated with 1M H2SO4 (2.5mL). Then the solution was heated at 90C for 7h (kept sealed) and was neutralized with 1M NaOH to give cloudy solution. An extraction with EtOAc (saturated with H2O, 5mL×2) was done when the mixture was cool down, of which the aqueous solution was retrieved under reduced pressure. The H2O fraction was diluted and passed through a Sep-Pak C18 cartridge, which then analyzed by HPLC under the following method: column, Capcell Pak NH2 UG80; solvent, MeCN-H2O (3:1); flow rate, 0.5mL/min; detection, RI and OR. The identifications of d-glucose, l-arabinose, l-rhamnose, and l-fucose presenting in the polysaccharide parts were recognized by the polarities with those of authentic samples. They were detected at 589nm on a polarimeter that the optical rotation of 0.2% (w/v) of d-glucose, l-arabinose, l-rhamnose, and l-fucose consisting with a homologous standard distilled water solution.
  • 79
  • 3β,20α,24-trihydroxy-29-norolean-12-en-28-oic acid 24-O-β-L-fucopyranosyl-(1→2)-[α-L-arabinopyranosyl-(1→3)]-6-O-acetyl-β-D-glucopyranoside [ No CAS ]
  • [ 5328-37-0 ]
  • [ 2438-80-4 ]
  • [ 50-99-7 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; In methanol; at 90℃; for 7h; General procedure: The operation was carried out with a modified method reported.8,16 In brief, the solution of sample (each about 4.0mg) is homogenized in methanol (2.5mL), associated with 1M H2SO4 (2.5mL). Then the solution was heated at 90C for 7h (kept sealed) and was neutralized with 1M NaOH to give cloudy solution. An extraction with EtOAc (saturated with H2O, 5mL×2) was done when the mixture was cool down, of which the aqueous solution was retrieved under reduced pressure. The H2O fraction was diluted and passed through a Sep-Pak C18 cartridge, which then analyzed by HPLC under the following method: column, Capcell Pak NH2 UG80; solvent, MeCN-H2O (3:1); flow rate, 0.5mL/min; detection, RI and OR. The identifications of d-glucose, l-arabinose, l-rhamnose, and l-fucose presenting in the polysaccharide parts were recognized by the polarities with those of authentic samples. They were detected at 589nm on a polarimeter that the optical rotation of 0.2% (w/v) of d-glucose, l-arabinose, l-rhamnose, and l-fucose consisting with a homologous standard distilled water solution.
  • 80
  • 3β,20α,24-trihydroxy-29-norolean-12-en-28-oic acid 24-O-β-L-fucopyranosyl-(1→2)-6-O-acetyl-β-D-glucopyranoside [ No CAS ]
  • [ 2438-80-4 ]
  • [ 50-99-7 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; In methanol; at 90℃; for 7h; General procedure: The operation was carried out with a modified method reported.8,16 In brief, the solution of sample (each about 4.0mg) is homogenized in methanol (2.5mL), associated with 1M H2SO4 (2.5mL). Then the solution was heated at 90C for 7h (kept sealed) and was neutralized with 1M NaOH to give cloudy solution. An extraction with EtOAc (saturated with H2O, 5mL×2) was done when the mixture was cool down, of which the aqueous solution was retrieved under reduced pressure. The H2O fraction was diluted and passed through a Sep-Pak C18 cartridge, which then analyzed by HPLC under the following method: column, Capcell Pak NH2 UG80; solvent, MeCN-H2O (3:1); flow rate, 0.5mL/min; detection, RI and OR. The identifications of d-glucose, l-arabinose, l-rhamnose, and l-fucose presenting in the polysaccharide parts were recognized by the polarities with those of authentic samples. They were detected at 589nm on a polarimeter that the optical rotation of 0.2% (w/v) of d-glucose, l-arabinose, l-rhamnose, and l-fucose consisting with a homologous standard distilled water solution.
  • 81
  • [ 50-99-7 ]
  • [ 90-34-6 ]
  • C21H31N3O6 [ No CAS ]
  • 82
  • 3-O-{α-D-xylopyranosyl-(1→3)-α-L-arabinopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→3)]-2-(acetamido)-2-deoxy-β-D-glucopyranosyl}echinocystic acid 28-O-{β-D-apiofuranosyl-(1→3)-β-D-xylopyranosyl-(1→2)-[2-O-cinnamoyl-α-L-arabinopyranosyl-(1→4)]-6-O-acetyl-β-D-glucopyranosyl} ester [ No CAS ]
  • [ 58-86-6 ]
  • [ 639-97-4 ]
  • [ 5328-37-0 ]
  • [ 50-99-7 ]
  • [ 7512-17-6 ]
  • [ 510-30-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; water; at 85℃; for 2h; General procedure: Each saponin (2 mg) was hydrolyzed with 2 ml of 2 M HCl at 85 C during 2 h. After cooling, the solvent was removed under reduced pressure. The sugar mixture was extracted from the aqueous phase (10 ml) and washed with CH2Cl2 (3 × 5 ml). The combined CH2Cl2 extracts were washed with water to give after evaporation the aglycone moiety, which was compared with an authentic standard sample by Co-TLC. The sugars were first analyzed by TLC over silica gel (CHCl3-MeOH-H2O, 8:5:1) by comparison with standard samples. The absolute configuration of each monosaccharide was determined from GC-MS analysis of their trimethylsilylated derivatives by comparison with authentic samples using the method previously described (Chaabi et al., 2010). The following sugars were detected: D-glucose, 2-(acetamido)-2-deoxy-D-glucose, D-xylose, L-arabinose, and D-apiose.
  • 83
  • 3-O-{α-D-xylopyranosyl-(1→3)-α-L-arabinopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→3)]-2-(acetamido)-2-deoxy-β-D-glucopyranosyl}echinocystic acid 28-O-(β-D-apiofuranosyl-(1→3)-β-D-xylopyranosyl-(1→2)-{2-O-[(6S,2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoyl]-α-L-arabinopyranosyl-(1→4)}-6-O-acetyl-β-D-glucopyranosyl) ester [ No CAS ]
  • [ 58-86-6 ]
  • [ 639-97-4 ]
  • [ 5328-37-0 ]
  • [ 50-99-7 ]
  • [ 7512-17-6 ]
  • [ 510-30-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; water; at 85℃; for 2h; General procedure: Each saponin (2 mg) was hydrolyzed with 2 ml of 2 M HCl at 85 C during 2 h. After cooling, the solvent was removed under reduced pressure. The sugar mixture was extracted from the aqueous phase (10 ml) and washed with CH2Cl2 (3 × 5 ml). The combined CH2Cl2 extracts were washed with water to give after evaporation the aglycone moiety, which was compared with an authentic standard sample by Co-TLC. The sugars were first analyzed by TLC over silica gel (CHCl3-MeOH-H2O, 8:5:1) by comparison with standard samples. The absolute configuration of each monosaccharide was determined from GC-MS analysis of their trimethylsilylated derivatives by comparison with authentic samples using the method previously described (Chaabi et al., 2010). The following sugars were detected: D-glucose, 2-(acetamido)-2-deoxy-D-glucose, D-xylose, L-arabinose, and D-apiose.
  • 84
  • 3-O-{α-D-xylopyranosyl-(1→3)-α-L-arabinopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→3)]-2-(acetamido)-2-deoxy-β-D-glucopyranosyl}echinocystic acid 28-O-(β-D-apiofuranosyl-(1→3)-β-D-xylopyranosyl-(1→2)-{2-O-[(6S,2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoyl-3-O-cinnamoyl]-α-L-arabinopyranosyl-(1→4)}-6-O-acetyl-β-D-glucopyranosyl) ester [ No CAS ]
  • [ 58-86-6 ]
  • [ 639-97-4 ]
  • [ 5328-37-0 ]
  • [ 50-99-7 ]
  • [ 7512-17-6 ]
  • [ 510-30-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; water; at 85℃; for 2h; General procedure: Each saponin (2 mg) was hydrolyzed with 2 ml of 2 M HCl at 85 C during 2 h. After cooling, the solvent was removed under reduced pressure. The sugar mixture was extracted from the aqueous phase (10 ml) and washed with CH2Cl2 (3 × 5 ml). The combined CH2Cl2 extracts were washed with water to give after evaporation the aglycone moiety, which was compared with an authentic standard sample by Co-TLC. The sugars were first analyzed by TLC over silica gel (CHCl3-MeOH-H2O, 8:5:1) by comparison with standard samples. The absolute configuration of each monosaccharide was determined from GC-MS analysis of their trimethylsilylated derivatives by comparison with authentic samples using the method previously described (Chaabi et al., 2010). The following sugars were detected: D-glucose, 2-(acetamido)-2-deoxy-D-glucose, D-xylose, L-arabinose, and D-apiose.
  • 85
  • (25S)-spirost-5-en-3-ol 3-O-β-D-glucopyranosyl-(1→3)-[β-D-fucopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside [ No CAS ]
  • [ 2438-80-4 ]
  • [ 50-99-7 ]
  • D-galactose [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; methanol; In water; for 12h;Reflux; Glycoside 1 (10 mg) was dissolved in anhydrous MeOH (4 mL) containing HCl (5%), refluxedfor 12 h, cooled, and treated with an equal volume of H2O. The resulting precipitate was filtered off and demonstrated to beidentical to yamogenin (TLC, system 2a). The filtrate was neutralized with Ag2CO3, filtered, and evaporated to dryness.GC detected D-galactose, D-glucose, and D-fucose in a 1:2:1 ratio.
  • 86
  • [ 50-99-7 ]
  • [ 4282-32-0 ]
  • 87
  • [ 50-99-7 ]
  • [ 67-03-8 ]
  • 1-(2-methyl-6,9-dihydro-5H-pyrimido[4,5-e][1,4]diazepin-7-yl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With L-Lysine hydrochloride; In aq. phosphate buffer; at 120℃; for 4h;pH 7;Autoclave; A 5 L of solution containing -glucose (30m), -lysinemonohydrochloride (30m), <strong>[67-03-8]thiamine chloride hydrochloride</strong>(30m), and 0.5 sodium phosphate buer(pH 7) was autoclaved at 120C for 4h. Aer its pHwas adjusted to 8 by adding 2 NaOH, the solution wasapplied to a column of DIAION HP-20 (i.d. 60×400mm;Mitsubishi Chemical, Tokyo). Aer washing the columnwith water, the pigment was eluted with 0.1% HCl.Fractions containing the pigment were collected, beforethe pH of the combined solution was adjusted to about10 by adding 2 NaOH. e pigment was extracted fromthe solution with ethyl acetate. Afer the extract was con -centrated in vacuo, the obtained yellow paste was appliedto a column of silica gel (i.d. 28×220mm; silica gel 60,Merck, Darmstadt, Germany), which was eluted with amixture of ethyl acetate and methanol (32:1; v/v). Duringthis procedure, each fraction was monitored with thinlayer chromatography (TLC). Fractions containing thepigment were collected and placed on a refrigerator. As aresult, ca. 30mg of yellowish needle crystals of pyrizepinewere obtained.
  • 88
  • O-polysaccharide from E. coli O-serogroup 106 [ No CAS ]
  • [ 3458-28-4 ]
  • [ 50-99-7 ]
  • [ 7512-17-6 ]
  • 89
  • [ 50-99-7 ]
  • [ 71-43-2 ]
  • [ 123-31-9 ]
  • [ 497-76-7 ]
  • 90
  • [ 69-79-4 ]
  • [ 3371-50-4 ]
  • [ 7485-51-0 ]
  • [ 50-99-7 ]
  • [ 499-40-1 ]
YieldReaction ConditionsOperation in experiment
With Escherichia coli BL21 recombinant alpha-glucosidase; In aq. buffer; at 60 - 100℃; The reaction mixture, which consisted of 30% maltose and 5 g enzyme in sodium phosphatebuffer, was incubated at 60 C for 2 h. Reaction mixtures were incubated at 100 C for 5 min toinactivate the enzyme, and the samples were then centrifuged at 12,000 g for 10 min and analyzedby HPAEC.
  • 91
  • [ 50-99-7 ]
  • [ 50-70-4 ]
  • [ 5077-67-8 ]
  • [ 116-09-6 ]
  • 92
  • 3β,20α,24-trihydroxy-29-norolean-12-en-28-oic acid 24-O-β-L-fucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranoside [ No CAS ]
  • [ 58-86-6 ]
  • [ 2438-80-4 ]
  • [ 50-99-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In 1,4-dioxane; water; for 10h;Reflux; General procedure: Based on the reported procedure (Zhong et al. 2013), each 2 mg of compounds 1 and 2 was dissolved in 2 M HCl (dioxane:H2O, 1:1 v/v) and refluxed for 10 h. After removal of the HCl by evaporation and extraction with EtOAc, the H2O extract was again evaporated and dried invacuo to furnish a monosaccharide residue. The residue was dissolved in pyridine (1 mL) to which 2 mg L-cysteine methyl ester hydrochloride was added. The mixture was kept at 60Cfor 2 h, evaporated under an N2 stream, and dried in vacuo, then trimethylsilylated with N-trimethylsilylimidazole (0.2 mL) for 2 h. The mixture was partitioned between n-hexane and H2O (2 mL each), and the n-hexane extract was analyzed by gas chromatography (GC) under the following conditions: capillary column, HP-5 (30 m × 0.25 mm × 0.25 mum; Dikma); FID detector with a temperature of 280 C; injection temperature 250 C; initial temperature 160 C, then raised to 280 C at 5 C/min, final temperature maintained for 10 min; carrier gas, N2; carrier gas flow rate 3 mL/min; split ratio 10:1. The standard sugars underwent the same reaction and GC conditions. The retention times of persilylated D-xylose, L-arabinose, D-glucose, and L-fucose were found to be 15.705 min, 16.232 min, 19.035 min, and 19.418 min, respectively.
  • 93
  • intermedia B [ No CAS ]
  • [ 2150-45-0 ]
  • [ 58-86-6 ]
  • [ 50-99-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; at 90℃; for 2h; General procedure: The absolute configurations of the sugar moieties in the compounds 1-4 were determinedby the method of Tanaka et al. Sample (1 mg, each) was hydrolyzed with 2MHCl for 2 h at 90 C. The mixture was evaporated to dryness, and the residue was dissolvedin H2O and extracted with CHCl3. After the aqueous layer was dried, the residuewas dissolved in pyridine (1 mL) containing L-cysteine methyl ester (3 mg) (Sigma,USA) and heated at 60 C for 1 h. Then, o-tolyl isothiocyanate (5 lL) (Alfa Aesar, UK)was added to the mixture, which was heated at 60 C for 1 h. The reaction mixturewas directly analyzed by HPLC. Analytical HPLC was performed on a RP-C18 column(5 lm, 4.60250 mm; Phenomenex Gemini) at 35 C with isocratic elution using 25%CH3CN containing 0.1% formic acid for 40 min at a flow rate 0.8 mL/min. The peakswere detected with a UV detector at 250 nm. The derivatives of 1 and 2 both gavetwo peaks at tR 20.2 and 23.7 min. The derivatives of 3 and 4 both gave one peak attR 20.0 min. The derivatives of L-glucose, D-glucose, and D-xylose (Sigma, USA) weresubjected to the same method. The peaks were recorded at tR 18.4 (L-glucose), 20.3(D-glucose), and 23.5 (D-xylose) min, respectively.
YieldReaction ConditionsOperation in experiment
The colorimetric detection of glucose was performed with rGO/CM (2:1) catalyst in preoptimized conditions. 50muL of GOx (2 mg/ml) was dissolved in an equal amount (350 muL) of different glucose concentrations (10-100 muM) in PBS buffer (pH 7.1) and incubated at 35C. 100 muL of TMB (1 mM) was dissolved in 1.5 ml of NaAc-HAc buffer (pH 4.0) containing 100 muL of 0.1 mg/ml rGO/CM (2:1) concentration. This solution was mixed with glucose-containing a solution and the mixture was incubated at 35C. The obtained blue color was detected with UV/Vis. spectrophotometer and maximum absorbance was recorded at 652 nm. For real sample analysis, glucose content in human serum samples was detected with the same methodology. The serum samples of healthy volunteers collected from Ashirvad Pathology Laboratory were first centrifuged at 12000 rpm to remove the possible aggregates in serum samples. The supernatants were diluted by 150 folds and performed the same detection methods as described above. In a control experiment, 350 muL of glucose (100 muM), 350 muL of sucrose (5 mM), 350 muL of fructose (5 mM), 350 muL lactose (5mM), 100muL of maltose (5mM), 350muL of L-Leucine (5mM) 350muL of L-Valine (5mM) and 350muL of L-sistine were mixed with 50 muL of GOx (2mg/ml) and incubated at 35C for 10 min. After that, 1.5 ml of NaAc-HAc buffer (pH 4.0) containing the appropriate amount of rGO/CM (2:1) and TMB was mixed with the above mixture for selectivity analysis. Limit of detection and linearity range were calculated using equation LOD= (3*Std)/(slope of calibration line).
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Reason: Stable Isotope

Chemical Structure| 84270-10-0

A1267914[ 84270-10-0 ]

D-GLUCOSE (4-13C)

Reason: Stable Isotope

Chemical Structure| 106032-60-4

A1354474[ 106032-60-4 ]

D-GLUCOSE (2-D)

Reason: Stable Isotope

Chemical Structure| 40762-22-9

A276063[ 40762-22-9 ]

(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanal-1-13C

Reason: Stable Isotope

Chemical Structure| 110187-42-3

A282263[ 110187-42-3 ]

(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanal-1,2,3,4,5,6-13C6

Reason: Stable Isotope

Chemical Structure| 105931-74-6

A224445[ 105931-74-6 ]

D-glucose-2-13c

Reason: Stable Isotope