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:

tert-butyl-N-(2-(2-(2-(5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno(3,4-d)imidazol-6-yl)pentanoylamino)ethoxy)ethoxy)ethyl)carbamate

12-benzylthiododecanoic-(8-biotinoylamido-3,6-dioxaoctyl)amide

N-[3-(N-cholesteryl-2-nitrobenzenesulfonamido)propyl]biotinamide

N-(13-amino-4,7,10-trioxatridecanyl)-D-biotinamide

Refernces

• 1、 Chaturvedi, Dhirendra N.,Knittel, James J.,Hruby, Victor J.,Castrucci, Ana Maria de L.. "Synthesis and Biological Actions of HIghly Potent and Prolonged Acting Biotin-Labeled Melanotropins". . p. 1406 - 1410. Retrieved 1984.
• 2、 Jemielity, Jacek,Lukaszewicz, MacIej,Kowalska, Joanna,Czarnecki, Jakub,Zuberek, Joanna,Darzynkiewicz, Edward. "Synthesis of biotin labelled cap analogue - Incorporable into mRNA transcripts and promoting cap-dependent translation". . p. 8570 - 8574. Retrieved 2012.
• 3、 Warminski, Marcin,Warminska, Zofia,Kowalska, Joanna,Jemielity, Jacek. "mRNA Cap Modification through Carbamate Chemistry: Synthesis of Amino- and Carboxy-Functionalised Cap Analogues Suitable for Labelling and Bioconjugation". . p. 6153 - 6159. Retrieved 2015.
• 4、 -. "LIGAND LINKER SUBSTRATE". Page/Page column 13; 15. . Retrieved 2020/07/15.
• 5、 Tian, Dan-mei,Qiao, Jia,Bao, Yu-zhou,Liu, Jie,Zhang, Xiao-kun,Sun, Xue-long,Zhang, You-wei,Yao, Xin-sheng,Tang, Jin-shan. "Design and synthesis of biotinylated cardiac glycosides for probing Nur77 protein inducting pathway". supporting information. p. 707 - 712. Retrieved 2019/01/22.