2,5-dioxopyrrolidin-1-yl 6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}hexanoate

• ChemBase编号: 133354
• 分子式: C20H30N4O6S
• 平均质量: 454.5404
• 单一同位素质量: 454.1886057
• SMILES: C1CC(=O)N(C1=O)OC(=O)CCCCCNC(=O)CCCC[C@H]1[C@@H]2[C@H](CS1)NC(=O)N2
• Canonical SMILES: O=C(CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2)NCCCCCC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C20H30N4O6S/c25-15(7-4-3-6-14-19-13(12-31-14)22-20(29)23-19)21-11-5-1-2-8-18(28)30-24-16(26)9-10-17(24)27/h13-14,19H,1-12H2,(H,21,25)(H2,22,23,29)/t13-,14-,19-/m0/s1
• InChIKey: UVGHPGOONBRLCX-NJSLBKSFSA-N

名称和登记号

名称

• IUPAC标准名: 2,5-dioxopyrrolidin-1-yl 6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}hexanoate
• IUPAC传统名: 2,5-dioxopyrrolidin-1-yl 6-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}hexanoate
• 别名: (+)-Biotinamidocaproate N-hydroxysuccinimidyl ester; N-(+)-Biotinyl-6-aminocaproic acid N-succinimidyl ester; N-(+)-Biotinyl-6-aminohexanoic acid NHS ester; N-Succinimidyl N-biotinyl-6-aminocaproate; Succinimidyl 6-(biotinamido)hexanoate; Biotinamidohexanoic acid N-hydroxysuccinimide ester; NHS-LC-BIOTIN; Succinimidyl-6-(biotinamido) Hexanoate

登记号

• CAS号: 72040-63-2
• MDL号: MFCD00065502
• Beilstein号: 3577403
• PubChem SID: 24891665; 162227631
• PubChem CID: 83874

理论计算性质

• Acid pKa: 13.488997
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): -0.0014645612
• LogD (pH = 7.4): -0.0014632656
• Log P: -0.0014629316
• 摩尔折射率: 112.0646 cm^3
• 极化性: 44.219826 Å^3
• 极化表面积: 133.91 Å^2
• 可自由旋转的化学键: 13
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMF; DMF: soluble50 mg/mL (Stable up to 2 months in dry DMF.); DMF: soluble50 mg/mL, clear, faintly yellow; DMSO; H2O: ≤2 mg/mL (with sonication); Methanol
• 外观: powder; White Solid
• 熔点: 150-159°C; 169-171 °C

安全信息

• 保存条件: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• 保存注意事项: Moisture Sensitive
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

产品相关信息

• 纯度: ≥97.0% (TLC); ≥98% (TLC)
• Empirical Formula (Hill Notation): C20H30N4O6S

详细说明

Sigma Aldrich - B2643

Application
Biotinylation reagent incorporating an aminocaproyl spacer. This can reduce the steric hindrance in binding avidin to some biotinylated compounds. Typically coupled to primary amine in the pH range 6.5-8.5.

Sigma Aldrich - 14412

Other Notes
Preparation of biotinyl-6-aminocaproyl calmodulin which forms stable complexes with avidin-enzyme conjugates1

Toronto Research Chemicals - S690250

A biotinylation reagent incorporating an aminocaproyl “spacer”. This can reduce the steric hindrance in binding avidin to some biotinylated compounds when used to biotinylate both the antibody and the carrier in the Protein Avidin-Biotin Capture System.

参考文献

• Hofmann, K., et al.: Biochemistry, 21, 978 (1982)
• Leary, J.J., et al.: PNAS USA, 80, 4045, (1982)
• Suter, M., et al.: Immunology Letters, 13, 313 (1982)
• Gretch, D.R., et al.: Anal. Biochem., 163, 270 (1982)
• Burgess, T.L., et al.: J. Biol. Chem., 269 (3