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B2643

Sigma-Aldrich

Biotinamidohexanoic acid N-hydroxysuccinimide ester

≥98% (TLC), powder

Synonym(s):

(+)-Biotinamidocaproate N-hydroxysuccinimidyl ester, N-(+)-Biotinyl-6-aminocaproic acid N-succinimidyl ester, N-(+)-Biotinyl-6-aminohexanoic acid NHS ester, N-Succinimidyl N-biotinyl-6-aminocaproate, Succinimidyl 6-(biotinamido)hexanoate

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About This Item

Empirical Formula (Hill Notation):
C20H30N4O6S
CAS Number:
72040-63-2
Molecular Weight:
454.54
Beilstein:
3577403
MDL number:
MFCD00065502
UNSPSC Code:
12352203
PubChem Substance ID:
24891665
NACRES:
NA.46

Assay

≥98% (TLC)

form

powder

solubility

H2O: ≤2 mg/mL (with sonication)
DMF: 50 mg/mL (Stable up to 2 months in dry DMF.)

storage temp.

−20°C

SMILES string

[H][C@]12CS[C@@H](CCCCC(=O)NCCCCCC(=O)ON3C(=O)CCC3=O)[C@@]1([H])NC(=O)N2

InChI

1S/C20H30N4O6S/c25-15(7-4-3-6-14-19-13(12-31-14)22-20(29)23-19)21-11-5-1-2-8-18(28)30-24-16(26)9-10-17(24)27/h13-14,19H,1-12H2,(H,21,25)(H2,22,23,29)/t13-,14-,19-/m0/s1

InChI key

UVGHPGOONBRLCX-NJSLBKSFSA-N

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Application

Biotinamidohexanoic acid N-hydroxysuccinimide ester has been used in the biotinylation of antibodies.

Biochem/physiol Actions

Biotin is a label widely used in several biochemical applications and has a high affinity for avidin. A spacer chain is required to reduce steric hindrance while coupling biotin (a small molecule) to biopolymers (large molecules). Biotinamidohexanoic acid N-hydroxysuccinimide ester incorporates a 7-atom spacer with the N-succinimide leaving group. It can react with a primary amine in the pH range of 6.5-8.5. This biotinylation reagent incorporates an aminocaproyl spacer and thus can reduce the steric hindrance in binding avidin to some biotinylated compounds.

Disclaimer

Unless otherwise stated in our catalog or other company documentation accompanying the product(s), our products are intended for research use only and are not to be used for any other purpose, which includes but is not limited to, unauthorized commercial uses, in vitro diagnostic uses, ex vivo or in vivo therapeutic uses or any type of consumption or application to humans or animals.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Alana M Thackray et al.
The Biochemical journal, 401(2), 475-483 (2006-10-05)
PrPSc [abnormal disease-specific conformation of PrP (prion-related protein)] accumulates in prion-affected individuals in the form of amorphous aggregates. Limited proteolysis of PrPSc results in a protease-resistant core of PrPSc of molecular mass of 27-30 kDa (PrP27-30). Aggregated forms of PrP
Heike M Pirner et al.
The Journal of biological chemistry, 281(18), 12381-12389 (2006-03-15)
Biotin is a water-soluble vitamin that functions as a prosthetic group in carboxylation reactions. In addition to its role as a cofactor, biotin has multiple roles in gene regulation. We analyzed biotin effects on gene expression in the yeast Saccharomyces
C Hughes et al.
Molecular therapy : the journal of the American Society of Gene Therapy, 3(4), 623-630 (2001-04-26)
Three strategies have been designed to concentrate infectious retroviral vectors from the supernatants of human- (HT1080) and murine- (NIH 3T3) based packaging cells. Streptavidin-conjugated paramagnetic particles in conjunction with (i) antibodies directed against murine fibronectin, (ii) biotinylated lectins, or (iii)
Avidin binding of carboxyl-substituted biotin and analogues.
K Hofmann et al.
Biochemistry, 21(5), 978-984 (1982-03-02)
S M Costello et al.
Clinical chemistry, 25(9), 1572-1580 (1979-09-01)
Classically, one can increase the titer of an agglutinating or first antibody with an antiglobulin or second antibody. We have used an avidin-biotin system in place of antiglobulin to similarly extend the agglutination by an initial anticellular antibody. Erythrocytes were
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