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Chemical Structure| 66640-86-6 Chemical Structure| 66640-86-6
Chemical Structure| 66640-86-6

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Biotin Hydrazide is a carbonyl-reactive biotinylation reagent, which is a carbonyl probe.

4.5 *For Research Use Only !

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Product Details of Biotin Hydrazide

CAS No. :66640-86-6
Formula : C10H18N4O2S
M.W : 258.34
SMILES Code : NNC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12
MDL No. :MFCD00078532
InChI Key :KOZWHQPRAOJMBN-ZKWXMUAHSA-N
Pubchem ID :83872

Safety of Biotin Hydrazide

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of Biotin Hydrazide

* 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 [ 66640-86-6 ]

[ 66640-86-6 ] Synthesis Path-Downstream   1~54

  • 1
  • [ 608-16-2 ]
  • [ 66640-86-6 ]
YieldReaction ConditionsOperation in experiment
296.0 mg With hydrazine; In methanol; at 20℃; for 17h; To a suspension of biotin (300 mg, 1.23 mmol) in MeOH (3 mL) was addedSOCl2 (0.30 mL, 4.0 mmol), and the solution was stirred overnight at roomtemperature to give a clear solution. After evaporation of the solvent and excessSOCl2 under reduced pressure, biotin methyl ester was obtained. The biotin methyl ester was used without further purification. Biotin methyl ester was dispersed inMeOH (3 mL), and hydrazine (0.175 mL, 2.92 mmol) was added with stirring. Afterstirring for 17 h, the solution was concentrated under reduced pressure and dilutedwith water (50 mL). The aqueous layer was washed by CH2Cl2 (30 mL × 3), andconcentrated in vacuo to give Biotinylhydrazine. Biotinylhydrazine was obtained as awhite solid powder (296.0 mg, about 100percent).
  • 2
  • [ 1121-60-4 ]
  • [ 66640-86-6 ]
  • 5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid [1-pyridin-2-yl-meth-(E)-ylidene]-hydrazide [ No CAS ]
  • 3
  • [ 66640-86-6 ]
  • [ 10111-08-7 ]
  • 5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid [1-(1H-imidazol-2-yl)-meth-(E)-ylidene]-hydrazide [ No CAS ]
  • 4
  • [ 66640-86-6 ]
  • 2,2-bis(1H-pyrazol-1-yl)acetic acid [ No CAS ]
  • 5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid N'-(2,2-di-pyrazol-1-yl-acetyl)-hydrazide [ No CAS ]
  • 5
  • [ 66640-86-6 ]
  • gramicidin A [ No CAS ]
  • biotin-tagged gramicidin A [ No CAS ]
  • 6
  • [ 66640-86-6 ]
  • alamethicin [ No CAS ]
  • biotin-tagged alamethicin [ No CAS ]
  • 7
  • [ 66640-86-6 ]
  • poly[3-(N-succinimido-p-phenylcarboxylate(tetraethoxy)oxy)-4-methylthiophene]-2,5-diyl}; monomer(s): 3-(N-succinimido-p-phenylcarboxylate(tetraethoxy)oxy)-4-methylthiophene [ No CAS ]
  • poly[3-(p-phenyl(carbonylhydrazonobiotin)(tetraethoxy)oxy)-4-methylthiophene]-2,5-diyl}; monomer(s): 3-(N-succinimido-p-phenylcarboxylate(tetraethoxy)oxy)-4-methylthiophene; biotin hydrazine [ No CAS ]
  • 8
  • [ 66640-86-6 ]
  • CH3C(O)-Aib-Pro-Aib-Ala-Aib-Ala-Gln(Trt)-Aib-Val-Aib-Gly-Leu-Aib-Pro-Val-Aib-Aib-Glu(O-t-Bu)-Gln(Trt)-Phe-COOH [ No CAS ]
  • CH3C(O)-Aib-Pro-Aib-Ala-Aib-Ala-Gln(Trt)-Aib-Val-Aib-Gly-Leu-Aib-Pro-Val-Aib-Aib-Glu(O-t-Bu)-Gln(Trt)-Phe-C(O)-(N2-biotinoylhydrazino-) [ No CAS ]
  • 9
  • [ 851138-53-9 ]
  • [ 66640-86-6 ]
  • [ 845869-41-2 ]
YieldReaction ConditionsOperation in experiment
Terthiophenes 1 and 2 were prepared by the sequence shown in Figure 1. The 3'- (2-hydroxyethyl)-2, 2' : 5', 2"-terthiophene was prepared by a modified literature method (Scheib and BaeUERLE, 1999; Higgins et AL, 2001), and esterified with excess succinyl chloride to give 1 after workup. Terthiophene 1 was activated with 1,2, 2,2- tetrachloroethyl-N-succinimidyl carbonate (Jaouadi et AL, 1987), then reacted with commercially-available <strong>[66640-86-6]biotin hydrazide</strong> to give 2.
  • 10
  • fucan B, MW = 21.5 kDa [ No CAS ]
  • [ 66640-86-6 ]
  • biotinylated fucan B [ No CAS ]
  • 11
  • 5\-d(CTCCCAGGCXCA), X = 2\-O-(2-oxoethyl)arabinouridine [ No CAS ]
  • [ 66640-86-6 ]
  • 5-d(CTCCCAGGCXCA), X = 2-O-(2-[5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoyl]hydrazono}ethyl)arabinouridine [ No CAS ]
  • 12
  • 5\-d(CXCCCAGGCTCA), X = 2\-O-(2-oxoethyl)arabinouridine [ No CAS ]
  • [ 66640-86-6 ]
  • 5-d(CXCCCAGGCTCA), X = 2-O-(2-[5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoyl]hydrazono}ethyl)arabinouridine [ No CAS ]
  • 13
  • 5\-d(CXCCCAGGCXCA), X = 2\-O-(2-oxoethyl)arabinouridine [ No CAS ]
  • [ 66640-86-6 ]
  • 5-d(CXCCCAGGCXCA), X = 2-O-(2-[5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoyl]hydrazono}ethyl)arabinouridine [ No CAS ]
  • 14
  • <i>N</i>-(2-oxo-ethyl)-4-(3-trifluoromethyl-3<i>H</i>-diazirin-3-yl)-benzamide [ No CAS ]
  • [ 66640-86-6 ]
  • <i>N</i>-(2-[5-(2-oxo-hexahydro-thieno[3,4-<i>d</i>]imidazol-6-yl)-pentanoyl]-hydrazono}-ethyl)-4-(3-trifluoromethyl-3<i>H</i>-diazirin-3-yl)-benzamide [ No CAS ]
  • 15
  • [ 952210-10-5 ]
  • [ 66640-86-6 ]
  • C88H122N4O26S [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% In methanol; at 60℃; for 72h; Aldehyde (16) (90 mg, 0.062 mmol) and (+) -<strong>[66640-86-6]biotin hydrazide</strong>(16.1 rag, 0.062 mmol) were combined in CH3OH (4 mL) and heated for 72 hr at 60 0C. After evaporation of the solvent, the crude material was purified by silica flash chromatography [CH2Cl2- CH3OH (10:1), R.f = 0.51]. The fractions containing product were collected and the solvent removed in vacuo to give the (19) (103 mg, 98 percent) ;HRMS-ES" (m/z) : [M] Na2+ calcd for [C88H122N4O26S]2+: 852.9034; found 853.9055.
  • 16
  • CTCCCAGGC-[N3-(2,4-dinitrophenylsulfenyl)-2'-O-(2-oxoethyl)arabinouridine]-CA [ No CAS ]
  • [ 66640-86-6 ]
  • CTCCCAGGC-[N3-(2,4-dinitrophenylsulfenyl)-2'-O-((+)-biotinylNHN=CHCH2)arabinouridine]-CA [ No CAS ]
  • 17
  • C-[N3-(2,4-dinitrophenylsulfenyl)-2'-O-(2-oxoethyl)arabinouridine]-CCCAGGCTCA [ No CAS ]
  • [ 66640-86-6 ]
  • C-[N3-(2,4-dinitrophenylsulfenyl)-2'-O-((+)-biotinylNHN=CHCH2)arabinouridine]-CCCAGGCTCA [ No CAS ]
  • 18
  • C-[N3-(2,4-dinitrophenylsulfenyl)-2'-O-(2-oxoethyl)arabinouridine]-CCCAGGC-[N3-(2,4-dinitrophenylsulfenyl)-2'-O-(2-oxoethyl)arabinouridine]-CA [ No CAS ]
  • [ 66640-86-6 ]
  • C-[N3-(2,4-dinitrophenylsulfenyl)-2'-O-((+)-biotinylNHN=CHCH2)arabinouridine]-CCCAGGC-[N3-(2,4-dinitrophenylsulfenyl)-2'-O-((+)-biotinylNHN=CHCH2)arabinouridine]-CA [ No CAS ]
  • 19
  • C27H37NO6S [ No CAS ]
  • [ 66640-86-6 ]
  • C37H53N5O7S2 [ No CAS ]
  • 20
  • [ 66640-86-6 ]
  • schizophyllan [ No CAS ]
  • schizophyllan-biotin [ No CAS ]
  • 21
  • [ 1000783-83-4 ]
  • [ 66640-86-6 ]
  • C164H282N12O44S [ No CAS ]
  • 22
  • C152H263N11O41 [ No CAS ]
  • [ 66640-86-6 ]
  • C162H279N15O42S [ No CAS ]
  • 23
  • [ 1012043-27-4 ]
  • [ 66640-86-6 ]
  • [ 1012043-29-6 ]
  • 24
  • [ 1070418-04-0 ]
  • [ 66640-86-6 ]
  • C59H83N16O20PS [ No CAS ]
  • 25
  • C29H35F3N4O12S [ No CAS ]
  • [ 66640-86-6 ]
  • C39H51F3N8O13S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% EXAMPLE 23Manufacture of the Compound (28) from the Compounds (26) and (27)The compound (26) (72 mg, 0.1 mmol) was dissolved in 1 ml of dichloromethane, then N-hydroxysuccinimide (13 mg, 0.11 mmol) and DCC (23 mg, 0.11 mmol) were added thereto and the mixture was stirred at room temperature for 1 hour. The solvent was evaporated therefrom under reduced pressure, the residue was dissolved in DMSO (1 ml), <strong>[66640-86-6]biotin hydrazide</strong> (compound (27)) (26 mg, 0.1 mmol) was added thereto and the mixture was stirred overnight at room temperature. The reaction solution was directly purified by a silica gel column chromatography (eluting with chloroform:methanol=5:1) to give the compound (28) (10 mg, 10percent) as a pale yellow solid. Positive ion FABMS (3-nitrobenzylalcohol) m/z: 961 (M+H)+.
  • 26
  • [ 1002342-83-7 ]
  • [ 66640-86-6 ]
  • [ 1207091-93-7 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; dichloromethane; water; at 20℃; for 16h; Preparation of iV-(2-(2-(2-(2-Azidoethoxy)ethoxy)ethoxy) acetaldehyde Biotinyl- hydrazone (1). To an anhydrous CH2Cl2 solution (2 mL) of oxalyl chloride (0.10 mL, 1.10 mmol) maintained at -78 °C under Ar was slowly added freshly distilled DMSO (0.19 mL, 3.29 mmol). The mixture was stirred (30 min), and then dry 4 (0.20 g, 0.91 mmol) was added via syringe. The mixture was stirred for an additional 30 min at -78 °C, and then Et3N (0.78 mL, 6.57 mmol) was added (10 min) and the mixture was stirred (15 min) at this temperature and warmed to ambient temperature. The reaction solution was diluted with CH2Cl2 (10 mL) and washed with H2O (2 x 10 mL). The organic layer was dried (Na2SO4), concentrated, and the crude aldehyde 5 (0.19 g, 0.88 mmol) was dissolved in CH2Cl2 (1 mL) and added to a solution of 6 (0.15 g, 0.58 mmol) in THFVH2O (1 : 1, 5 mL). The reaction mixture was allowed to stir at room temperature (16 h), the solvent was evaporated in vacuo, and then the crude product purified by column chromatography (SiO2; 1/9 MeOH/CHCl3) to yield 0.20 g (74percent) of 1 as a white solid: mp 134-135 0C; R1= 0.35 (1/9 MeOH/CHCl3); IR (nujol) 2924, 2101, 1667, 1557, 1459 cm"1; 1H NMR (CD3OD) (minor conformer in parenthesis (a mixture of conformers similar to other hydrazones (Syakaev et al. 2006))) delta 1.45-1.52 (m, C(6)H2), 1.58-1.79 (m, C(7)H2, C(8)H2), 2.27 (t, J = 7.4 Hz, C(9)H2 (2.65 (t, J = 7.5 Hz, C(9)H2))), 2.71 (d, J- 12.6 Hz, C(5)HH'), 2.93 (dd, J= 4.7, 12.6 Hz, C(5)HH'), 3.18-3.25 (m, C(2)H), 3.37 (t, J = 4.8 Hz, N3CH2), 3.65-3.69 (m, 2 OCH2CH2O, N3CH2CH2), 4.18 (d, J = 5.3 Hz, OCH2CHN (4.15 (d, J= 5.3 Hz, OCH2CHN))), 4.31 (dd, J- 4.2, 7.6 Hz, C(3)H), 4.49 (dd, J = 4.7, 7.6 Hz, C(4)H), 7.49 (t, J= 5.3 Hz, OCH2CHN (7.33 (t, J= 5.3 Hz, OCH2CHN))); 13C NMR (CD3OD) (minor conformer in parenthesis) delta 26.0 (26.6) (C(6)), 29.6 (C(7)), 29.9 (30.0) (C(8)), 33.2 (35.2) (C(9)), 41.2 (C(5)), 51.9 (N3CH2), 57.1 (57.2) (C(2)), 61.8 (C(3)), 63.5 (C(4)), 71.2, 71.3, 71.4, 71.5, 71.7, 71.8 (3 CH2OCH2), 145.6 (149.3) (OCH2CHN), 166.3 (C(2')), 172.7 (177.9) (C(IO)); HRMS (ESI) 458.2182 [M + H+] (calcd. for Ci8H32N7O5S 458.2186); Anal. (C18H3iN7O5S, 0.25 H2O) Calcd.: C, 46.79percent; H, 6.87percent; N, 21.22percent; S, 6.94percent. Found: C, 46.67percent; H, 6.82percent; N, 20.88percent; S, 6.88percent.
  • 27
  • C85H90N2O26S2 [ No CAS ]
  • [ 66640-86-6 ]
  • [ 1227413-17-3 ]
  • 28
  • C25H21NO8S2 [ No CAS ]
  • [ 66640-86-6 ]
  • C31H34N4O7S3 [ No CAS ]
  • 29
  • [ 1227413-32-2 ]
  • [ 66640-86-6 ]
  • [ 1227413-14-0 ]
  • 30
  • [ 3326-32-7 ]
  • [ 66640-86-6 ]
  • C31H29N5O7S2 [ No CAS ]
  • 31
  • [ 91853-90-6 ]
  • [ 66640-86-6 ]
YieldReaction ConditionsOperation in experiment
With hydrazine hydrate;Heating; To a suspension of homobiotin 14b (150 mg, 0.58 mmol) in dry methanol (1.5 ml) was added drop-wise thionyl chloride (276 mg, 169 muL, 2.32 mmol) and stirred under a nitrogen atmosphere for 2 h. The mixture was concentrated in vacuo, suspended in methanol (2 ml) and was added hydrazine hydrate (0.5 ml) and stirred for 16 h. The reaction mixture was concentrated in vacuo, dissolved in water (5 ml) and washed with chloroform (2 x 5 ml). The aqueous layer was concentrated in vacuo to give a white powder (121 mg, 77percent).
  • 32
  • [ 1395347-05-3 ]
  • [ 66640-86-6 ]
  • C22H30N4O2S4 [ No CAS ]
  • 33
  • [ 1226145-00-1 ]
  • [ 66640-86-6 ]
  • C20H22Cl2N4O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethylsulfoxide-d6; at 20℃; for 96h; General procedure: To a solution of beta-keto ester 4 (100 mg, 0.38 mmol) in EtOH (10 mL) was added the substituted hydrazine (2 equiv. 0.76 mmol) and the solution stirred at room temperature over night. The solvent was removed in vacuo and the residue purified by column chromatography (20:1 DCM:MeOH) to provide the title compound. NMR data is reported for the major tautomer observed.
  • 34
  • [ 66640-86-6 ]
  • chondroitin disaccharide 0-S [ No CAS ]
  • [ 1419703-15-3 ]
  • 35
  • (-)-brevenal [ No CAS ]
  • [ 66640-86-6 ]
  • C49H76N4O9S [ No CAS ]
  • 36
  • [ 1428361-03-8 ]
  • [ 66640-86-6 ]
  • [ 1428360-83-1 ]
  • 3-[4-[5-[4-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]butyl]-1H-1,2,4-triazol-3-yl]butyl]-5-methyl-1,3-benzoxazol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; toluene; at 150℃; for 2h;Microwave irradiation; To a suspension of <strong>[66640-86-6]biotin hydrazide</strong> 15a2 (28 mg, 0.108 mmol) in anhydrous DMF (0.5 ml) were added imidic ester 19 (32 mg, 0.102 mmol), DIPEA (52 mg, 0.410 mmol) and anhydrous toluene (0.5 ml). The mixture was stirred and microwaved at 150 oC for 2 h (with variable pressure and power), concentrated in vacuo and purified by silica gel chromatography eluting with 5percent methanol in dichloromethane to give 1,2,4-oxadiazole 5 (16 mg, 33percent) and eluting at 12percent methanol in dichloromethane to give 1,2,4-triazole 3 (7 mg, 15percent)
  • 38
  • C153H225N43O48S [ No CAS ]
  • [ 66640-86-6 ]
  • HSQGTFTSDYSKY-((2S)-N-[(1S,3E)-3-({5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}imino)-1-carbamoylpropyl]-2-amino-4-methylpentanamide)-SRRAQDFVQWLMNT [ No CAS ]
  • 39
  • [ 1613697-49-6 ]
  • [ 66640-86-6 ]
  • C68H89N5O19S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With pyridine; In dimethyl sulfoxide; at 0 - 20℃; for 96h; A solution of SB-T-1214-(SS-linker OSu (0.069 g, 0.269 mmol) and <strong>[66640-86-6]biotinylhydrazine</strong> (0.336 g, 0.269 mmol) in a 3:1 mixture of DMSO-pyridine (2.7 mL) was cooled to 0 °C, and the mixture was reacted for 4 d at room temperature. Purification of the crude product by column chromatography on silica gel with 7percent CH3OH in CH2C12 as eluent gave 15 (0.175 g, 47percent) as a white solid: 1H NMR (400 MHz, CD3OD) delta 1.02 (m, 2H), 1.10 (m, 2H), 1.20 (s, 6H), 1.30 (d, J = 6.8 Hz, 3H), 1.44 (s, 9H), 1.49 (m, 2H), 1.63 (m, 4H), 1.68 (s, 3H), 1.76 (s, 3H), 1.78 (s, 3H), 1.81 (m, 3H), 1.94 (s, 3H), 1.99 (m, 2H), 2.28 (t, J = 7.6 Hz, 2H), 2.35 (m, 2H), 2.41 (s, 3H), 2.48 (m, 2H), 2.71 (d, J= 12 Hz, 1H), 2.93 (dd, J= 5.0, 12.7 Hz, 1H), 2.98 (m, 1H), 3.22 (m, 1H), 3.87 (d, J= 7.2 Hz, 1H), 4.03 (d, J= 2.4, 16.7, 1H), 4.13 (d, J= 1.8, 16.7 Hz, 1H), 4.20 (d, J = 8.4 Hz, 1H), 4.24 (d, J= 8.4 Hz, 1H), 4.32 (m, 2H), 4.50 (dd, J= 4.4, 8.0 Hz, 1H), 4.59 (s, 2H), 4.94 (d, J= 2.4 Hz, 2H), 5.03 (d, J= 7.6 Hz, 1H), 5.28 (bs, 1H), 5.69 (d, J= 7.2 Hz, 1H), 6.16 (bt, J= 9.0 Hz, 1H), 6.48 (s, 1H), 7.33 (m, 3H), 7.53 (t, J= 8.0 Hz, 2 Hz), 7.66 (t, J= 7.4 Hz, 1H), 7.83 (d, J= 7.8 Hz, 1H), 8.15 (d, J = 7.2 Hz, 2H); 13C NMR (125 MHz, CD3OD) delta 7.81, 7.84, 9.06, 12.41, 13.64, 17.27, 19.46, 19.57, 20.99, 21.89, 24.73, 24.98, 25.59, 27.41, 27.96, 28.14, 30.61, 30.90, 32.98, 35.35, 36.14, 38.13, 39.03, 39.67, 43.20, 45.78, 45.90, 46.68, 49.32, 55.54, 57.88, 60.25, 61.85, 70.92, 71.58, 74.92, 75.18, 75.34, 76.06, 77.70, 79.11, 80.93, 84.49, 119.83, 127.51, 128.06, 128.30, 129.75, 130.01, 130.09, 130.12, 131.01, 133.19, 133.37, 133.53, 137.28, 137.40, 137.54, 141.24, 156.09, 164.75, 166.20, 168.91, 170.08, 170.10, 170.89, 172.67, 173.47, 173.72, 203.76; HRMS (TOF) for C68H9oN5019S3+ calcd: 1376.5387. Found: 1376.5397 (Delta = 0.7 ppm). HPLC (A): RT = 12.1 min, purity > 99percent.
  • 40
  • C62H74F2N2O20S2 [ No CAS ]
  • [ 66640-86-6 ]
  • C68H87F2N5O19S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With pyridine; In dimethyl sulfoxide; at 0 - 20℃; for 72h; To a solution of 15 (87 mg, 0.069 mmol) and 16 (28 mg, 0.11 mmol) in DMSO (0.5 mL) at 0 °C was added pyridine (0.15 mL), and the mixture was allowed to warm from 0 °C to room temperature and react for 72 h with stirring. The reaction mixture was directly concentrated in vacuo to afford a yellow-green oil. Purification of the crude product by column chromatography on silica gel with 6percent CH3OH in CH2Cl2 as eluent gave BLT-F2 (1) as a white solid (62 mg, 77percent): mp 129-131 °C; 1H NMR (500 MHz, CD3OD): delta 1.03-1.24 (m, 4H), 1.23 (s, 3H), 1.24-1.32 (m, 5H), 1.38-1.70 (m, 4H), 1.33 (s, 3H), 1.42 (s, 9H), 1.60-1.72 (m, 1H), 1.74 (s, 3H), 1.81 (m, 1H), 1.83 (s, 3H), 1.84 (s, 3H), 1.92 (m, 1H), 1.97 (s, 3H), 2.11 (m, 3H), 2.24-2.52 (m, 4H), 2.42 (s, 3H), 2.54-2.72 (m, 2H), 2.83 (br s, 4H), 2.87 (m, 2H), 3.22 (m, 1H), 3.88 (d, J = 7.2 Hz, 1H), 3.93 (s, 2H), 4.21 (d, J = 8.4 Hz, 1H), 4.27 (d, J = 8.4 Hz, 1H), 4.48 (dd, J = 6.6, 10.5 Hz, 1H), 4.74-4.32 (m, 1H), 4.49 (m, 1H), 4.88 (m, 2H), 5.05 (d, J = 8.1 Hz, 1H), 5.39 (d, J = 6.0 Hz, 1H), 5.70 (d, J = 7.2 Hz, 1H), 6.23 (t, J = 9.0 Hz, 1H), 6.37 (s, 1H), 6.94 -7.02 (m, 2H), 7.381 (t, J = 8.4 Hz, 1H), 7.53 (m, 1H), 7.75 (dd, J = 6.0, 8.4 Hz, 1H), 7.86 (d, J = 9.0 Hz, 1H), 7.97 (d, J = 7.8 Hz, 1H); 13C NMR (125 MHz, CD3OD): delta 7.78, 8.99, 12.38, 13.59, 17.22, 19.41, 19.49, 20.93, 24.96, 25.55, 27.36, 27.94, 29.35, 30.53, 30.90, 32.96, 35.35, 36.11, 38.15, 39.03, 39.64, 43.16, 45.72, 46.67, 49.30, 55.51, 57. 86, 60.26, 61.84, 70.15, 70.91, 71.59, 75.32, 75.44, 75.94, 77.69, 79.11 80.96, 84.45, 114.87, 115.09, 116.11, 116.34, 117.68, 117.91, 119.78, 119.93, 120.15, 125.68, 130.29, 130.37, 132.32, 132.39, 132.97, 133.36, 133.45, 136.67, 137.30, 141.25, 156.09, 161.16, 161.37, 163.60, 163.81, 164.74, 164.88, 168.82, 169.98; 19F NMR (376 MHz, CD3OD): delta -112.95 (s, 1F), -111.88 (s, 1F). HRMS (TOF): Calcd. for C68H88F2N5O19S3+: 1412.5204: Found: 1412.5159 (Delta = -3.2 ppm).
  • 41
  • [ 66640-86-6 ]
  • C29H38N4O12Rh2S [ No CAS ]
  • C29H38N4O12Rh2S [ No CAS ]
  • 42
  • [ 66640-86-6 ]
  • [ 619-05-6 ]
  • C17H24N6O3S [ No CAS ]
  • 43
  • [ 1571-30-8 ]
  • [ 66640-86-6 ]
  • C20H23N5O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% To a suspension of 8-hydroxyquinoline-2-carboxylic acid (51mg, 0.27mmol) in dry DMF (7mL) were added 1-hydroxybenzotriazole monohydrate (37mg, 0.27mmol) and DCC (56mg, 0.27mmol). After 1h, <strong>[66640-86-6]biotin hydrazide</strong> (70mg, 0.27mmol) was added. The reaction mixture was stirred for 48h at room temperature, filtered off and then evaporated to dryness. The crude product was purified by precipitation in water and then silica flash chromatography (dichlromethane/methanol 98:2). (0045) Yield: 64mg (55percent); Positive ion ESI-MS: m/z=430.0 [P+H]+, 452.1 [P+Na]+, 468.1 [P+K]+, 880.9 [2P+Na]+, 896.9 [2P+K]+; 1H NMR (500MHz, (CD3)2SO) delta (ppm): 11.20 (s, 1H, NH), 10.18 (s, 1H, OH), 10.04 (s, 1H, NH), 8.53 (d, 1H, J4,3=8.6Hz, H-4 of HQ), 8.12 (d, 1H, J4,3=8.6Hz, H-3 of HQ), 7.59 (t, 1H, J=7.9Hz, H-6 of HQ), 7.50 (dd, 1H, J5,6=8.2Hz, J5,7=1.2Hz, H-5 of HQ), 7.18 (dd, 1H, J7,6=7.6Hz, J7,5=1.2Hz, H-7), 6.45 (s, 1H, NH of biotin), 6.38 (s, 1H, NH of biotin), 4.32 (m, 1H, H-9 of biotin), 4.16 (m, 1H, H-10 of biotin), 3.14 (m, 1H, H-6 of biotin), 2.84 (dd, 1H, J8,8?=12.5 and J8,9=5.1Hz, H-8 of biotin), 2.59 (d, 1H, J8?,8=12.5Hz, H-8? of biotin), 2.25 (m, 2H, Hs-2 of biotin), 1.61 (m, 3H, H-5 and Hs-3 of biotin), 1.45 (m, 3H, Hs-4 and H-5? of biotin); 13C NMR (125MHz, (CD3)2SO) delta (ppm): 171.9 (C=O groups), 162.9 (C-12 of biotin), 153.9 (C-8 of HQ), 146.7 (C-2 of HQ), 138.3 (C-4 of HQ), 136.6 (C-9 of HQ), 130.0 (C-10 and C-6 of HQ), 119.3 (C-3 of HQ), 118.0 (C-5 of HQ), 112.2 (C-7 of HQ), 61.6 (C-10 of biotin), 59.6 (C-9 of biotin), 55.9 (C-6 of biotin), 40.4 (C-8 of biotin), 33.5 (C-2 of biotin), 28.4 (C-4 and C-5 of biotin), 25.6 (C-3 of biotin).
  • 44
  • [ 14510-06-6 ]
  • [ 66640-86-6 ]
  • 8-hydroxyquinolylbiotin hydrazone [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% In ethanol; for 24h;Reflux; 8-Hydroxy-2-quinolinecarboxaldehyde (47mg, 0.27mmol) was added to <strong>[66640-86-6]biotin hydrazide</strong> (70mg, 0.27mmol) in absolute ethanol (25mL). The reaction was refluxed under stirring for 24h. After cooling, the product precipitated and then was collected by filtration and recrystallized from ethanol. (0047) Yield: 88mg (79percent); Positive ion ESI-MS: m/z=414.1 [P+H]+, 436.1 [P+Na]+, 826.8 [2P+H]+, 848.8 [2P+Na]+; 1H NMR (500MHz, (CD3)2SO) delta (ppm): 11.70 (s, NH, isomer B), 11.64 (s, NH, isomer A), 9.79 (s, OH), 8.36 (s, CH=N, isomer B), 8.31 (d, J4,3=8.7Hz, H-4 of HQ), 8.21 (s, CH=N, isomer A), 8.02 (m, H-3 of HQ), 7.49?7.34 (m, H-5 and H-6 of HQ), 7.11 (t, J=7.0Hz, H-7), 6.42 (s, H-11 of biotin), 6.34 (s, H-13 of biotin), 4.31 (m, H-9 of biotin), 4.15 (m, H-10 of biotin), 3.14 (m, H-6 of biotin), 2.82 (m, H-8 of biotin), 2.72 (t, J=7.4Hz, Hs-2 of biotin, isomer A), 2.58 (m, H-8? of biotin), 2.28 (m, H-2 of biotin, isomer B), 1.67 (m, H-5 and Hs-3 of biotin), 1.59?1.35 (m, Hs-4 and H-5? of biotin). 13C NMR (125MHz, (CD3)2SO) delta (ppm): 175.2 (C=O, isomer A), 169.13 (C=O, isomer B), 163.2 (C-12 of biotin), 154.1 (C-8 of HQ), 152.1 (C-2 of HQ), 146.6 (CH=N, isomer B), 143.2 (CH=N, isomer A), 138.6 (C-9 of HQ), 136.9 (C-4 of HQ), 135.0 (C-10 of HQ), 128.5 (C-6 of HQ), 118.0 (C-3 and C-5 of HQ), 112.5 (C-7 of HQ), 61.4 (C-10 of biotin), 59.6 (C-9 of biotin), 55.8 (C-6 of biotin), 40.2 (C-8 of biotin), 34.4 (C-2 of biotin, isomer B), 32.1 (C-2 of biotin, isomer A), 28.6 (C-4 and C-5 of biotin), 24.9 (C-3 of biotin).
  • 45
  • [ 1610596-19-4 ]
  • [ 66640-86-6 ]
  • (9H-fluoren-9-yl)methyl 1,2-dimethyl-2-((1-(3-oxo-3-(2-(5-((3aS,4R,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoyl)hydrazinyl)propyl)-1H-indol-2-yl)methyl)hydrazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.18 g With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 19h; j00086j A solution of 5-((3 aS,4S,6aR)-2-oxohexahydro- 1 H-thieno [3 ,4-d]imidazol- 4-yl)pentanehydrazide (0.10 g, 0.39 mmol ), (9H-fluoren-9-yl)methyl 1,2-dimethyl-2- ((1 -(3 -oxo-3 -(perfluorophenoxy)propyl)- 1 H-indol-2-yl)methyl)hydrazine- 1- carboxylate (0.28 g, 0.43 mmol) and DIPEA (0.14 g, 1.04 mmol) in DMF (1.94 mE) was stirred in room temperature for 19 h. The mixture was concentrated under reduced pressure, and then was purified by Cl 8 silica gel chromatography (0- 10 percent MeOH in dichloromethane) to give(9H-fluoren-9-yl)methyl 1 ,2-dimethyl-2-(( 1-(3 -oxo-3 -(2-(5-((3 aS,4R,6aR)-2-oxohexahydro- 1 H-thieno [3 ,4-d] imidazol-4-yl)pentanoyl)hydrazinyl)propyl)- 1 H-indol-2-yl)methyl)hydrazine- 1 -carboxylate (2a) (0.18 g). ESI-MS: mlz 724 (M + H)+.
  • 46
  • [ 41991-02-0 ]
  • [ 66640-86-6 ]
  • C15H20N4O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% To a solution of 202 mg (1 mmol, 1 eq) of 2,5-dimethoxy-2,5-dihydron acetate in furolide was added 4 mL0.1 M aqueous HCI was stirred at room temperature for 3 h. The reaction system was neutralized to neutral with sodium bicarbonate solids and 0.4 mL of 500 mM was addedHEPES buffer (50 mM, pH 7.5) to adjust the pH to 7.5. To the resulting mixture was added 129 mg (0.5 mmol, 0.5 eq)A solution of <strong>[66640-86-6]biotin hydrazide</strong> in DMSO (3 mL) was reacted at room temperature for 1 h. Part of the solvent was removed by steaming and the remaining solution was filtered with reverse phase HPLCTo give 71 mg (0.21 mmol, yield 42percent) of brown solid.
  • 47
  • [ 57683-72-4 ]
  • [ 66640-86-6 ]
  • C20H29N5O11S2 [ No CAS ]
  • 48
  • [ 66640-86-6 ]
  • C19H22O11Rh2 [ No CAS ]
  • C29H38N4O12Rh2S [ No CAS ]
  • 49
  • [ 66640-86-6 ]
  • C19H22O11Rh2 [ No CAS ]
  • C29H38N4O12Rh2S [ No CAS ]
  • 50
  • [ 66640-86-6 ]
  • C30H48N9O9Pol [ No CAS ]
  • C40H64N13O10PolS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 24h; General procedure: Fully-protected thymopentin attached to a resin was synthesizedby standard SPPS. Fmoc-protected amino acid (0.2 mmol)was anchored to Wang resin (0.05 mmol) by using EDC/HOBt(0.2 mmol) in DMF (4 mL), and the Fmoc group was removed bytreatment with 20 vol percent piperidine in DMF (5 mL). To removethe OAll group, the resin was treated with Pd(PPh3)4 (0.2 mmol)and PhSiH3 (0.5 mmol) in CH2Cl2 (4 mL). The mixture wasshaken at r.t. for 12 h. The solvent was then removed by filtration,and the resin was washed with CH2Cl2 (3 × 5 mL) and DMF (3 × 5 mL). Side-chain modifications were performed by usingvarious modifiers under the appropriate conditions (Scheme 1).For TA1, MPEG6-OH (0.2 mmol), HOBt (0.2 mmol), DIC (0.2mmol), DMAP (0.1 mmol) were dissolved in DMF (4 mL). ForTA2?TA6: R?H (0.2 mmol), HOBt (0.2 mmol), HBTU (0.2 mmol),and DIPEA (0.2 mmol) were dissolved in DMF (4 mL) [R?H = e.g.,MPEG6-NH2, glucosamine·HCl, 2-(biotinamido)ethylamine,<strong>[66640-86-6]biotin hydrazide</strong>, or dansylhydrazine]. For all reactions, thereaction mixture was shaken at r.t. for 24 h. The solvent wasremoved by filtration and the resin was washed with CH2Cl2(3 × 5 mL) and DMF (3 × 5 mL). The resin was then suspended in20percent piperidine/DMF for 30 min to remove the Fmoc group. Thepeptide was cleaved from the resin with 50 vol percent TFA in CH2Cl2(5 mL) for 2 h. The residue was dissolved in H2O then freezedriedto give the solid. The crude product was finally purified bypreparative RP-HPLC.
  • 51
  • [ 66640-86-6 ]
  • [ 148-53-8 ]
  • C18H24N4O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In ethanol; for 5h;Reflux; Weigh 2.58 g of <strong>[66640-86-6]biotin hydrazide</strong> and 1.52 g of o-vanillin in a container.Add 150 mL of ethanol and reflux for 5 h to obtain a yellow solid product.The yield was 78percent.
  • 52
  • [ 23605-05-2 ]
  • [ 66640-86-6 ]
  • C39H58N4O12S [ No CAS ]
  • C39H58N4O12S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid; In methanol; at 60℃; for 10h; General procedure: Biotinylatedcardiac glycoside chemical probes were synthesize following the nucleophilicaddition reaction, and subsequent dehydration under the catalysis of 1percent AcOH. To asolution of cardiac glycoside (beta-Antiarin or alpha-Antiarin, 1 eq.) and Biotin-linkerproduct (Biotinylhydrazine, Biotin-AAn-CONHNH2 and Biotin-PEG(n+1)-CONHN2,about 7 eq.) in MeOH was added 1percent AcOH. The reaction mixture was stirred andrefluxed for 10h at 60°. The crude product was obtained by concentrated underreduced pressure. The residue was purified by semipreparative RP-HPLC (17percentACN-H2O or 35percent MeOH-H2O) to obtain Biotinylated cardiac glycoside chemicalprobes (P1a-P8a and P1b-P8b).
  • 53
  • [ 639-13-4 ]
  • [ 66640-86-6 ]
  • C39H58N4O12S [ No CAS ]
  • C39H58N4O12S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid; In methanol; at 60℃; for 10h; General procedure: Biotinylatedcardiac glycoside chemical probes were synthesize following the nucleophilicaddition reaction, and subsequent dehydration under the catalysis of 1percent AcOH. To asolution of cardiac glycoside (beta-Antiarin or alpha-Antiarin, 1 eq.) and Biotin-linkerproduct (Biotinylhydrazine, Biotin-AAn-CONHNH2 and Biotin-PEG(n+1)-CONHN2,about 7 eq.) in MeOH was added 1percent AcOH. The reaction mixture was stirred andrefluxed for 10h at 60°. The crude product was obtained by concentrated underreduced pressure. The residue was purified by semipreparative RP-HPLC (17percentACN-H2O or 35percent MeOH-H2O) to obtain Biotinylated cardiac glycoside chemicalprobes (P1a-P8a and P1b-P8b).
  • 54
  • [ 66640-86-6 ]
  • C39H19N9OSZn [ No CAS ]
  • C49H37N13O3S2Zn [ No CAS ]
 

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