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B8271

Sigma-Aldrich

Bromoacetic acid N-hydroxysuccinimide ester

≥95%, powder

Synonym(s):

2,5-Dioxopyrrolidin-1-yl 2-bromoacetate, N-Hydroxysuccinimide bromoacetate

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About This Item

Empirical Formula (Hill Notation):
C6H6BrNO4
CAS Number:
42014-51-7
Molecular Weight:
236.02
MDL number:
MFCD00058571
UNSPSC Code:
12352106
PubChem Substance ID:
24892067
NACRES:
NC.07

Quality Level

200

Assay

≥95%

form

powder

reaction suitability

reagent type: cross-linking reagent

solubility

acetone: 25 mg/mL
DMF: soluble

functional group

NHS ester

shipped in

dry ice

storage temp.

−20°C

SMILES string

O=C(N1OC(CBr)=O)CCC1=O

InChI

1S/C6H6BrNO4/c7-3-6(11)12-8-4(9)1-2-5(8)10/h1-3H2

InChI key

NKUZQMZWTZAPSN-UHFFFAOYSA-N

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Application

A heterobifunctional cross-linking reagent which allows bromoacetylation of primary amine groups followed by coupling to sulfhydryl-containing compounds. Typically, initial reaction couples via ester to primary amine by amide bond formation in the pH range 6.5-8.5. The second reaction results in thioether bonding in pH range 7.0-8.0.

Caution

The bromoacetyl group is light sensitive.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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N Kolodny et al.
Analytical biochemistry, 187(1), 136-140 (1990-05-15)
A method described here for conjugating synthetic peptides to carrier proteins provides a convenient method for determining peptide-to-carrier protein ratios. N-Bromoacetyl-containing peptides are reacted in situ with carrier proteins in which the disulfide bonds were reduced with tri-n-butylphosphine. At pH
M S Bernatowicz et al.
Analytical biochemistry, 155(1), 95-102 (1986-05-15)
Synthetic peptides derived from human fibrin were unidirectionally conjugated to three carrier proteins (bovine serum albumin, bovine alpha-lactalbumin, and keyhole limpet hemocyanin) by a method that employs N-succinimidyl bromoacetate. This heterobifunctional crosslinking reagent was prepared with a 79% yield in
John S Mort et al.
Methods in molecular medicine, 100, 237-250 (2004-07-29)
The use of synthetic peptides to generate rabbit polyclonal anticatabolic neoepitope antibodies that can be used to study the presence of defined proteolytic cleavage sites in aggrecan is described. Principles of peptide design and methods for preparation and characterization of

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