N-Succinimidyl bromoacetate  (Synonyms: NHS-Bromoacetate)

N-Succinimidyl bromoacetate (NHS-Bromoacetate) is a heterobifunctional crosslinking reagent, mainly used to modify the ɛ-amino group of lysine side chains. By covalently linking its bromoacetyl moiety to the ɛ-amino group of lysine in peptidomimetics, N-Succinimidyl bromoacetate enables their conjugation with thiol-modified nanoparticles via thioether bonds. N-Succinimidyl bromoacetate also performs bromoacetylation modification on carrier proteins, which then forms stable thioether bonds with the thiol groups of cysteine in peptides, thus efficiently preparing soluble peptide-protein conjugates with high substitution ratios. N-Succinimidyl bromoacetate can be used to prepare activated Sepharose derivatives for affinity chromatography, protein affinity labeling reagents, and peptide-protein immunogen conjugates with non-immunogenic linkages. N-Succinimidyl bromoacetate is applicable to studies related to HIV-1 infection and glioblastoma multiforme^[1][2][3].

N-Succinimidyl bromoacetate serves as a crosslinker to successfully conjugate glioma fusion junction peptides with KLH^[1].
N-succinimidyl bromoacetate (9 mmol relative to 26 mmol of free side-chain amines in the peptide polymer; 15 min, room temperature) bromoacetylates 28% of the free side-chain amine groups on the HIV-1MN gp120 C4 domain peptide polymer within 15 minutes at room temperature, without disrupting the α-helical structure of the peptide polymer^[2].
N-succinimidyl bromoacetate performs bromoacetylation modification on BLA (60 mg; 3.0 mL buffer), and the protein recovery rate reaches 94% after gel filtration^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Immunization with peptide-protein conjugates prepared using N-succinimidyl bromoacetate (50 μg peptide; intradermal; intraperitoneal; primary immunization, then boost after 4 weeks) elicits anti-peptide, anti-fibrin monomer, and anti-carrier protein antibodies of comparable immunoreactivity to those elicited by maleimido-linked conjugates, while the S-carboxymethyl linkage introduced by N-succinimidyl bromoacetate is not immunogenic^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

236.02

C₆H₆BrNO₄

42014-51-7

Solid

White to off-white

O=C(CBr)ON1C(CCC1=O)=O

Room temperature in continental US; may vary elsewhere.

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

• [1]. Humphrey PA, et al. Anti-synthetic peptide antibody reacting at the fusion junction of deletion-mutant epidermal growth factor receptors in human glioblastoma. Proc Natl Acad Sci U S A. 1990;87(11):4207-4211.

  [2]. Frey A, et al. Peptomer aluminum oxide nanoparticle conjugates as systemic and mucosal vaccine candidates: synthesis and characterization of a conjugate derived from the C4 domain of HIV-1MN gp120[J]. Bioconjugate chemistry, 1997, 8(3): 424-433.

  [3]. Bernatowicz MS, et al. Preparation of peptide-protein immunogens using N-succinimidyl bromoacetate as a heterobifunctional crosslinking reagent. Anal Biochem. 1986;155(1):95-102.  [Content Brief]