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

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

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

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(35013-72-0)Related Product Information

• Sulfo-NHS-Biotin
• BIOTIN-XX-NHS
• Succinimidyl 6-(biotinamido)hexanoate
• N-Hydroxysuccinimide
• BIOTIN DISULFIDE N-HYDROXY-SUCCINIMIDE ESTER
• methyl 5-[(1S,2S,5R)-7-oxo-3-thia-6,8-diazabicyclo[3.3.0]oct-2-yl]pent anoate
• BIOTIN HYDRAZIDE
• (+)-BIOTIN-EPSILON-AMINOCAPROIC ACID
• D-BIOTIN P-NITROPHENYL ESTER
• Biotin-NHCH2CH2-SS-Pyr
• Biotin-SLC-NHS
• Succinimide
• BIOTIN-NHS
• DESTHIOBIOTIN N-HYDROXYSUCCINIMIDYL ESTER
• 2,5-Dioxopyrrolidin-1-yl octanoate
• D-DESTHIOBIOTIN
• D-biotin-d-sulfoxide
• 7,8-DIAMINOPELARGONIC ACID