BIOTIN-NHS CAS 35013-72-0

Introduction：Basic information about BIOTIN-NHS CAS 35013-72-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

BIOTIN-NHS Basic information

• Product Name: BIOTIN-NHS
• Synonyms: (+)-biotin-n-hydroxysuccimide ester;n-hydroxysuccimidobiotin;BIOTIN-OSU: N-HYDROXYSUCCINIMIDOBIOTIN;d-Biotin NHS ester;(2,5-dioxopyrrolidin-1-yl) 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoate;5-(2-OXO-HEXAHYDRO-THIENO[3,4-D]IMIDAZOL-6-YL)-PENTANOIC ACID 2,5-DIOXO-PYRROLIDIN-1-YL ESTER;D-(+)BIOTIN N-HYDROXYSUCCINIMIDE ESTER;D-BIOTIN-N-HYDROXYSUCCINIMIDE ESTER
• CAS: 35013-72-0
• MF: C14H19N3O5S
• MW: 341.38
• EINECS: 609-055-0
• Product Categories: biotinyl;BiotinylationReagents;Biotinylation Reagents;Cross Linking Reagents;Biotin Derivatives;PEG
• Mol File: 35013-72-0.mol

BIOTIN-NHS Chemical Properties

• Melting point: 212-214 °C
• density: 1.45±0.1 g/cm3(Predicted)
• storage temp.: -20°C
• solubility: DMF: ≤50 mg/mL Stable for at least one month in dry DMF
• form: powder
• pka: 13.89±0.40(Predicted)
• color: White to off-white
• BRN: 4720781
• Stability: Stable. Incompatible with strong oxidizing agents.
• InChI: InChI=1S/C14H19N3O5S/c18-10-5-6-11(19)17(10)22-12(20)4-2-1-3-9-13-8(7-23-9)15-14(21)16-13/h8-9,13H,1-7H2,(H2,15,16,21)/t8-,9-,13-/m0/s1
• InChIKey: YMXHPSHLTSZXKH-RVBZMBCESA-N
• SMILES: C1(=O)N[C@]2([H])[C@H](CCCCC(ON3C(=O)CCC3=O)=O)SC[C@]2([H])N1
• CAS DataBase Reference: 35013-72-0(CAS DataBase Reference)

Safety Information

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10-23
• HS Code: 2934 99 90
• Storage Class: 11 - Combustible Solids

BIOTIN-NHS Usage And Synthesis

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.

Chemical Properties

White Solid

Uses

amine reactive biotinylation reagent

Uses

Amino reactive biotin reagent for preparing biotinylated surfaces or polypeptides.

Uses

Biotin-NHS is used in the biotinylation of proteins and peptides. Couples with primary amine in the pH range 6.5-8.5.

reaction suitability

reaction type: Biotinylations

Synthesis

6066-82-6

58-85-5

35013-72-0

GENERAL STEPS: To a mixed solution of D-biotin (0.82 mmol, 200 mg) and N-hydroxybutanediimide (0.89 mmol, 102 mg) was added 3-(ethyliminomethylamino)-N,N-dimethylpropan-1-amine hydrochloride (0.96 mmol, 184 mg). The reaction mixture was stirred at room temperature overnight and then concentrated to give a white solid. The crude product was mixed with isopropanol, heated to 70 °C and cooled. The pure product was obtained by filtration as a white powder in 91% yield (0.75 mmol, 255 mg).

Purification Methods

Recrystallise the ester from refluxing isoPrOH and dry it in a vacuum over P2O5 + KOH. [Jasiewicz et al. Exp Cell Biol 100 213 1976.]

References

[1] Journal of the American Chemical Society, 2007, vol. 129, # 45, p. 13987 - 13996
[2] New Journal of Chemistry, 2013, vol. 37, # 11, p. 3762 - 3769
[3] Organic Letters, 2013, vol. 15, # 16, p. 4130 - 4133
[4] Journal of Materials Chemistry, 2004, vol. 14, # 17, p. 2638 - 2642
[5] Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 784 - 791

BIOTIN-NHS Preparation Products And Raw materials

• Raw materials: 1H-Imidazole, 1-[5-[(3aS,4S,6aR)-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-1-oxopentyl]--->TSTU-->D-Biotin-->N-Hydroxysuccinimide
• Preparation Products: biotinylamidoethylacetamide-->LC-LC(+)-Biotin-->N-BIOTINYL-3,6,9-TRIOXAUNDECANE-1,11-DIAMINE-->D-BIOTINOL-->(+)-BIOTIN-EPSILON-AMINOCAPROIC ACID-->FMOC-LYS(BIOTIN)-OH-->4-((Biotinoyl)amino)Butyric acid-->N-[6-[[5-[(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-1 -oxopentyl]amino]hexyl]-carbamic Acid 1,1-Dimethylethyl Ester