Amino acid derivative and bromoacetyl modified peptides

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

C - Chemistry, Metallurgy

07

K

C07K 5/02 (2006.01) A61K 47/48 (2006.01) C07C 271/22 (2006.01) C07K 1/00 (2006.01) C07K 1/04 (2006.01) C07K 1/107 (2006.01) C07K 17/00 (2006.01)

Patent

CA 2111465

A new amino acid derivative, N.alpha.-tert-butoxycarbonyl-N.epsilon.-(N-bromoacetyl-.beta.-alanyl)-L-lysine (BBAL), has been synthes- ized as a reagent to be used in solid-phase peptide synthesis for introducing a side-chain bromoacetyl group at any desired posi- tion in a peptide sequence. The bromoacetyl group subsequently serves as a sulfhydryl-selective cross-liking function for the pre- paration 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 thi- oether 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 therapeu- tics, and for substances such as peptides linked to polymers, plastics, enamels and ceramics.

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