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

• ChemBase ID: 133354
• Molecular Formular: C20H30N4O6S
• Molecular Mass: 454.5404
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}hexanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 6-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}hexanoate
• Synonyms: (+)-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

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 13.488997
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.0014645612
• LogD (pH = 7.4): -0.0014632656
• Log P: -0.0014629316
• Molar Refractivity: 112.0646 cm^3
• Polarizability: 44.219826 Å^3
• Polar Surface Area: 133.91 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 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
• Apperance: powder; White Solid
• Melting Point: 150-159°C; 169-171 °C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Moisture Sensitive
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

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

DETAILS

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.

REFERENCES

• 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