NHS-Biotin

Base Information

• Chemical Name: NHS-Biotin
• CAS No.: 35013-72-0
• Molecular Formula: C14H19N3O5S
• Molecular Weight: 341.388
• Hs Code.: 2934 99 90
• European Community (EC) Number: 609-055-0
• UNII: 30M534A3CQ
• DSSTox Substance ID: DTXSID40956451
• Nikkaji Number: J227.824C
• Wikidata: Q76391048
• ChEMBL ID: CHEMBL3781011
• Mol file: 35013-72-0.mol

Synonyms:biotinyl N-hydroxysuccinimide ester;N-hydroxysuccinimido biotin;N-hydroxysuccinimidobiotin;NHS-biotin

Chemical Property of NHS-Biotin

Chemical Property:

• Appearance/Colour: White Solid
• Melting Point: 212-214 °C
• Refractive Index: 1.616
• PKA: 13.89±0.40(Predicted)
• PSA: 130.11000
• Density: 1.45 g/cm³
• LogP: 0.91490
• Storage Temp.: −20°C
• Solubility.: DMF: ≤50 mg/mL Stable for at least one month in dry D
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 341.10454189
• Heavy Atom Count: 23
• Complexity: 525

Purity/Quality:

99% ^*data from raw suppliers

NHS-Biotin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)CCCCC2C3C(CS2)NC(=O)N3
• Isomeric SMILES: C1CC(=O)N(C1=O)OC(=O)CCCC[C@H]2[C@@H]3[C@H](CS2)NC(=O)N3
• Description: N-Hydroxysuccinimide (NHS) activates carboxylic acid groups (on biotin) to facilitate coupling reactions. Biotin-NHS is a compound used to attach biotin to primary amines under alkaline conditions (pH~8-9). For example, lysines on the surface of proteins, including antibodies, are ideal targets for biotinylation with this compound.
• Uses: amine reactive biotinylation reagent Biotin-NHS is used in the biotinylation of proteins and peptides. Couples with primary amine in the pH range 6.5-8.5. Amino reactive biotin reagent for preparing biotinylated surfaces or polypeptides.

Technology Process of NHS-Biotin

There total 8 articles about NHS-Biotin 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: 90.7%

O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (105832-38-0) + biotin (58-85-5,22879-79-4) → biotin N-Hydroxysuccinimide ester (35013-72-0)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.bmcl.2021.128244

Reference yield: 90.0%

di(succinimido) carbonate (74124-79-1) + biotin (58-85-5,22879-79-4) → biotin N-Hydroxysuccinimide ester (35013-72-0)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1002/ejic.201800644

Reference yield: 90.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + (3aS,4S,6aR)-4-[5-(1H-imidazol-1-yl)-5-oxopentyl]tetrahydro-1H-thieno-[3,4-d]imidazol-2(3H)-one (101187-31-9) → biotin N-Hydroxysuccinimide ester (35013-72-0)

Guidance literature:

In N,N-dimethyl-formamide;

DOI:10.1021/jm00377a005

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

(3aS,4S,6aR)-4-[5-(1H-imidazol-1-yl)-5-oxopentyl]tetrahydro-1H-thieno-[3,4-d]imidazol-2(3H)-one

di(succinimido) carbonate

biotin

Downstream raw materials:

5-(2-oxohexahydrothieno[3,4-d]imidazol-6-yl)pentanoic acid bis(2-diphenylphosphanyl-ethyl)amide

5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid [2-(4-hydroxy-3,5-diiodo-phenyl)-ethyl]-amide

Boc-Lys(biotinyl)-OH

3-<2-N-(biotinyl)aminoethyldithio>propanoic acid

Refernces

Novel non-nucleosidic phosphoramidites for oligonucleotide modification and labeling

10.1016/S0960-894X(97)00278-3

The research focuses on the synthesis of novel non-nucleosidic phosphoramidites and controlled pore glass (CPG) supports, which are based on a cyclohexyl-4-amino-1,1-dimethanol backbone. The purpose of this study was to develop a series of reagents that could be used to label oligonucleotides with biotin and fluorescein at various positions, including the 5'-, 3'-, and internal sites. The researchers aimed to improve the efficiency of synthesis and mimic the stereochemical properties of the natural polynucleotide backbone, while also keeping the reporter groups away from the oligonucleotide chain to enhance hybridization efficiency. The key chemicals used in the process included 3-cyclohexene-1,1-dimethanol, benzoyl chloride, sodium borohydride, BF3-Et2O, hydroxylamine-O-sulfonic acid, biotin-N-hydroxysuccinimide ester (biotin-NHSu), fluorescein-NHSu, and various other reagents for the protection, deprotection, and coupling steps. The conclusions of the research were that these novel biotin, fluorescein, and amino labeled phosphoramidites and CPG supports could be used advantageously for the introduction of multiple reporter groups onto oligonucleotides in a cost-effective and efficient manner, retaining the natural 3-carbon atom internucleotide phosphate distance in DNA/RNA, which does not affect the hybridization and annealing properties of the duplex.