The United States of America As Represented by the Secretary of

Raymond L Fields

Frank A Robey

Wolfgang F Lindner

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.

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Mount Airy, MD, United States of America

Raymond L Fields