Succinimidyl 6-(biotinamido)hexanoate

Base Information

• Chemical Name: Succinimidyl 6-(biotinamido)hexanoate
• CAS No.: 72040-63-2
• Molecular Formula: C20H30N4O6S
• Molecular Weight: 454.547
• Hs Code.: 29349990
• DSSTox Substance ID: DTXSID90992728
• Nikkaji Number: J671.769A
• Wikidata: Q72509039
• Mol file: 72040-63-2.mol

Synonyms:BACHS;biotin-amidocaproate-N-hydroxysuccinimide ester;biotinyl-6-aminocaproic acid N-hydroxysuccinimide ester;biotinyl-epsilon-aminohexanoic acid N-hydroxysuccinimide ester;N-biotinyl-epsilon-aminocaproic acid N-hydroxysuccinimide ester;succinimidyl-6-biotinamide hexanoate

Chemical Property of Succinimidyl 6-(biotinamido)hexanoate

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 169-171 °C
• Refractive Index: 1.591
• PKA: 13.90±0.40(Predicted)
• PSA: 159.21000
• Density: 1.35 g/cm³
• LogP: 1.98240
• Storage Temp.: −20°C
• Solubility.: H2O: ≤2 mg/mL with sonication
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 13
• Exact Mass: 454.18860586
• Heavy Atom Count: 31
• Complexity: 702

Purity/Quality:

98%,99%, ^*data from raw suppliers

NHS-LC-Biotin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)CCCCCNC(=O)CCCCC2C3C(CS2)NC(=O)N3
• Isomeric SMILES: C1CC(=O)N(C1=O)OC(=O)CCCCCNC(=O)CCCC[C@H]2[C@@H]3[C@H](CS2)NC(=O)N3
• Description: Biotin-LC-NHS Ester has an extended spacer arm which helps to minimize steric hindrance. The membrane permeability of this reagent allows it to be used for intracellular labeling. It can react efficiently with primary amino (-NH2) to form stable, irreversible amide bonds.
• Uses: Has been used to biotinylate both the antibody and the carrier in the Protein Avidin-Biotin solid surfaces, such as plastics, which may reduce antigenicity. It has also been used to enhance the detection of DNA on nitrocellulose. Spacer Arm: A biotinylation reagent incorporating an aminocaproyl pacer? 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 Sy Succinimidyl 6-(biotinamido)hexanoate is 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. This system avoids the direct interaction of a captured antibody with solid surfaces, such as plastics, which may reduce antigenicity. It has also been used to enhance the detection of DNA on nitrocellulose. Has also been used as a cell surface labelling reagent

Technology Process of Succinimidyl 6-(biotinamido)hexanoate

There total 5 articles about Succinimidyl 6-(biotinamido)hexanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 56.8%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-hexanoic acid (72040-64-3) → 6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-hexanoic acid 2,5-dioxo-pyrrolidin-1-yl ester (72040-63-2)

Guidance literature:

6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-hexanoic acid; With pyridine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h;

1-hydroxy-pyrrolidine-2,5-dione; In N,N-dimethyl-formamide; for 18h;

DOI:10.1021/bc1001505

Reference yield:

biotin (4443-68-9,5652-41-5,57378-70-8,22879-79-4) → 6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-hexanoic acid 2,5-dioxo-pyrrolidin-1-yl ester (72040-63-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridine; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 0.08 h / 20 °C

1.2: 24 h / 20 °C

2.1: N,N-dimethyl-formamide / 4 h / 20 °C / pH 8 / sodium bicarbonate buffer

3.1: pyridine; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 0.08 h / 20 °C

3.2: 18 h

With pyridine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide;

DOI:10.1021/bc1001505

Reference yield:

biotin N-hydroxysuccinimide ester (85718-04-3) → 6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-hexanoic acid 2,5-dioxo-pyrrolidin-1-yl ester (72040-63-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N,N-dimethyl-formamide / 4 h / 20 °C / pH 8 / sodium bicarbonate buffer

2.1: pyridine; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 0.08 h / 20 °C

2.2: 18 h

With pyridine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide;

DOI:10.1021/bc1001505

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-hexanoic acid

biotin

biotin N-hydroxysuccinimide ester

Refernces

• 1、 Wang, Tzu-Pin,Chiou, Yi-Jang,Chen, Yi,Wang, Eng-Chi,Hwang, Long-Chih,Chen, Bing-Hung,Chen, Yen-Hsu,Ko, Chun-Han. "Versatile phosphoramidation reactions for nucleic acid conjugations with peptides, proteins, chromophores, and biotin derivatives". experimental part. p. 1642 - 1655. Retrieved 2011/11/06.