Synthesis of chloroacetyl and bromoacetyl modified peptides for

Details Synthesis of chloroacetyl and bromoacetyl modified peptides for Synthesis of chloroacetyl and bromoacetyl modified peptides for

1988-12-13

1991-11-19

Nutter, Nathan M.

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

525 5411, 528288, 530317, 530335, 530336, 530337, 530345, A61K 3702, C08G 6344, C08G 6391, C08G 6900

Patent

active

050667165

ABSTRACT:
A method to incorporate bromoacetyl and chloroacetyl moieties on amino groups of synthetic peptides using a standard program with an automated peptide synthesizer has been developed. The bromoacetyl and chloroacetyl-derivatized peptides react well with sulfhydryl-containing proteins and with peptides containing cysteine residues. Autopolymerization or cyclization occurs by reaction of the free sulfhydryl of cysteine in a peptide with the bromoacetyl group (or chloroacetyl group) and reactions can generally be controlled by controlling the concentrations of starting peptide in neutral pH buffers. Analytical methods for evaluating the polymers or cyclized peptides include gel filtration chromatography, reverse phase HPLC, SDS-PAGE and amino acid analysis where the degree of reaction can be evaluated by quantifying the amount of S-carboxymethylcysteine formed after HCl hydrolysis. N-bromoacetyl-derivatized peptides are useful as reagents for potential peptide immunogens, vaccines and therapeutics, and for substances such as peptides linked to polymers, plastics, enamels, and ceramics.

REFERENCES:
Lindner et al., "Automated Synthesis and Use of N-Chloroacetyl-Modified Peptides for the Preparation of Synthetic Peptide Polymers and Peptide-Protein Immunogenes", Int. J. Peptide Protein Res., 30, 1987, 794-800.

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