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Quality Control of Biotin-C5-amino-C5-amino Purity: 98% SDS Specification

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NMR

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Product Details of Biotin-C5-amino-C5-amino

CAS No. :	89889-51-0
Formula :	C₂₂H₃₈N₄O₅S
M.W :	470.63
SMILES Code :	O=C(O)CCCCCNC(CCCCCNC(CCCC[C@@H]1SC[C@]([C@]1([H])N2)([H])NC2=O)=O)=O
MDL No. :	MFCD06796002
InChI Key :	SRKRKWYAHKIBEW-FIKGOQFSSA-N
Pubchem ID :	22851428

Safety of Biotin-C5-amino-C5-amino

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of Biotin-C5-amino-C5-amino

* 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 [ 89889-51-0 ]

[ 89889-51-0 ] Synthesis Path-Downstream 1~10

1
[ 89889-51-0 ]
[ 18444-66-1 ]
[ 1227476-35-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2994 - 2997.

2
[ 88192-19-2 ]
[ 89889-51-0 ]
[ 1092173-29-9 ]

Yield	Reaction Conditions	Operation in experiment
25%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dimethyl sulfoxide; N,N-dimethyl-formamide; at 20℃;	To a solution of d-biotin-Acp-Acp-OH (54 mg, 0.114 mmol) in DMF/DMSO (5 mL) were added HOBt·H2O (16 mg, 0.114 mmol), EDC·HCl (22 mg, 0.114 mmol), and 3-azido propylamine (23 mg, 0.228 mol), and the mixture was stirred at room temperature overnight. The resultant precipitates were collected and washed with EtOAc. The precipitate was then purified by preparative HPLC (with a linear gradient of 10-60% CH3CN in 0.1% aq TFA over 40 min) to give a white powder of compound 20 (16 mg, 25%). 1H NMR (600 MHz, DMSO-d6) δ 1.18-1.38 (m, 10H), 1.42-1.54 (m, 7H), 1.58-1.65 (m, 3H), 2.00-2.04 (m, 6H), 2.57 (d, 1H, J = 12 Hz), 2.82 (dd, 1H, J = 5.0, 12 Hz), 2.99 (q, 4H, J = 6.0 Hz), 3.07-3.11 (m, 3H), 3.32-3.37 (m, 2H, overlapping with H2O), 4.11-4.13 (m, 1H), 4.30 (dd, 1H, J = 5.0, 7.7 Hz), 6.36 (s, 1H), 6.42 (s, 1H), 7.71 (t, 1H, J = 5.0 Hz), 7.74 (t, 1H, J = 5.0 Hz), 7.83 (t, 1H, J = 5.0 Hz); HRMS (ESI): m/z 553.3287 (M+H+) (calcd for C25H45N8O4S: 553.3284).

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 595 - 602.

3
[ 102-54-5 ]
[ 89889-51-0 ]
6-(6-biotinamidohexanamido)hexanoylferrocene [ No CAS ]

References: [1]Organometallics,2013,vol. 32,p. 5774 - 5783.

4
[ 72040-64-3 ]
[ 60-32-2 ]
[ 89889-51-0 ]

References: [1]Organometallics,2013,vol. 32,p. 5774 - 5783.

5
[ 89889-51-0 ]
(E)-N-(3-(5-(1-(4-(4-(2-aminoethyl)piperazin-1-yl)but-2-enoyl)-1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5-fluoro-2-methylphenyl)-4-cyclopropylbenzamide hydrochloride [ No CAS ]
4-cyclopropyl-N-(5-fluoro-2-methyl-3-(5-(1-((E)-4-(4-(2-(6-(6-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)hexanamido)hexanamido)ethyl)piperazin-1-yl)but-2-enoyl)-1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl)benzamide [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 1467 - 1472.

6
[ 89889-51-0 ]
[ 79498-31-0 ]
C₄₂H₆₄N₄O₈S [ No CAS ]
C₄₂H₆₄N₄O₈S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13.4%; 14%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 24h;	General procedure: A solution of glaucocalyxin A (332 mg, 1.0 mmol, 1.0 equiv) in DMF (20 ml) was added biotin (293 mg, 1.2 mmol, 1.2 equiv) and 1-ethyl-3(3-dimethylpropylamine)carbodiimide (EDCI, 383 mg, 2.0 mmol, 2.0 equiv) and DMAP (122 mg, 1.0 mmol, 1.0equiv) at room temperature. The reaction mixture was stirred at room temperature for 24 h. The reaction mixture was then diluted with water and extracted with ethyl acetate. The extract was washed with saturated NaCl (aqueous) solution, dried over anhydrous Na2SO4, filtered, and evaporated to give a white solid residue. The crude residue was purified by silica gel column, eluted with EtOAc/MeOH (12:1, v/v) to afford a mixture. Then the crude residue was further purified by preparative reversed phase liquid chromatography, elution with MeOH-H2O (70:30, v/v) at 3 ml/min to afford the desired compounds 5 and 6. Compounds 7, 8, 9, 10, 11, 12, 13a, 14a,13 b, 14 b,13c and 14c were obtained according to the similar procedure of preparing 5 and 6 starting from 1, 2, 3, 4a, 4b and 4c. GLA-biotin derivatives were all white solids. Compound 5, 280 mg, yield 50.2%. Compound 6, 101 mg, yield 18.1%.Compound 7, 251 mg, yield 18.0%. Compound 8, 121 mg, yield 37.4%. Compound 9,110 mg, yield 13.4%. Compound 10, 105 mg, yield 14.0%. Compound 11, 94 mg, yield 13.9%. Compound 12, 30 mg, yield 4.4%. Compound 13a, 102 mg, yield 15.1%. Compound 14a, 65 mg, yield 9.6%. Compound 13 b, 169 mg, yield 21.0%. Compound 14 b, 45 mg, yield 6.5%. Compound 13c, 96 mg, yield 13.8%. Compound 14c, 64 mg,yield 9.2%.