Amino acid derivative and bromoacetyl modified peptides for the

Details Amino acid derivative and bromoacetyl modified peptides for the Amino acid derivative and bromoacetyl modified peptides for the

1993-11-19

1995-08-22

Beisner, William H.

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

530317, 530322, 530335, 530336, 530337, 530345, 530350, 530402, 530409, 525 541, 525 5411, 528288, 560159, 562450, A61K 3702, C08G 6348

Patent

active

054441501

ABSTRACT:
A new amino acid derivative, N.sup..alpha. -tert-butoxycarbonyl-N.sup.e -(N-bromoacetyl-.beta.-alanyl)-L-lysine (BBAL), has been synthesized as a reagent to be used in solid-phase peptide synthesis for introducing a side-chain bromoacetyl group at any desired position in a peptide sequence. The bromoacetyl group subsequently serves as a sulfhydryl-selective cross-linking function for the preparation of cyclic peptides, peptide conjugates and polymers. BBAL residues are stable to final HF deprotection/cleavage. BBAL peptides can be directly coupled to other molecules or surfaces which possess free sulfhydryl groups by forming stable thioether linkages. Peptides containing both BBAL and cysteine residues can be self-coupled to produce either cyclic molecules or linear peptide polymers. Such peptide derivatives are useful in preparing potential peptide immunogens, vaccines and therapeutics, and for substances such as peptides linked to polymers, plastics, enamels and ceramics.

REFERENCES:
patent: 5066716 (1991-11-01), Robey et al.
Robey et al., Anal. Biochem., "Automated Synthesis of N-Bromoacetyl-Modified . . . " vol. 177, pp. 373-377 (1989).
Lindner et al., Int. J. Peptide Protein Res., "Automated synthesis and use of N-chloroacetyl-modified . . . " vol. 30, pp. 794-800 (1987).
Bernatowicz et al., Analytical Biochemistry, "Preparation of Peptide-Protein Immunogens . . . " vol. 155, pp. 95-102 (1986).
Kolodny et al., Analytical Biochemistry, "Conjugation of Synthetic Peptides to Proteins . . . " vol. 187, pp. 136-140 (1990).

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