Synthesis of peptides
AssigneeArmour Pharmaceutical Company
InventorsEmil Kaiser, Robert L. Colescott
Life of this patent
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Abstract
Resin peptides useful in the preparation of peptides having biological activity, and particularly such resin peptides containing Pro--Asp--CH.sub.2 -- or Pro--Asn--CH.sub.2 -- at one end of an amino acid chain, being the resin and Pro, Asp and Asn being the residues of the amino acids proline, aspartic acid and asparagine; and processes for the preparation of such resin peptides.
Claims10
A resin peptide having the structure:
- ##STR24## in which R is a crosslinked polystyrene resin, and Bz is benzyl, p-methoxybenzyl, p-chlorobenzyl, P-nitrobenzyl or benzhydryl.
A resin peptide having the structure:
- ##STR25## in which R is a crosslinked polystyrene resin, Bz is benzyl, P-methoxybenzyl, p-chlorobenzyl, P-nitrobenzyl or benzhydryl, and Y is H or Bz.
A resin peptide having the structure:
- ##STR26## in which R is a crosslinked polystyrene resin and Bz is benzyl, p-methoxybenzyl, p-chlorobenzyl, P-nitrobenzyl or benzhydryl,
- Y is H or Bz
- and V is carbobenzyloxy, 2-chlorocarbobenzyloxy, 2-bromocarbobenzyloxy, dichlorocarbobenzyloxy or trifluoroacetyl.
A resin peptide having the structure:
- ##STR27## in which R is a crosslinked polystyrene resin, and Bz is benzyl, p-methoxybenzyl, p-chlorobenzyl, p-nitrobenzyl or benzhydryl,
- Y is H or Bz,
- T is tosyl or nitro,
- W is carbobenzyloxy, tosyl, dinitrophenyl, Bz or H,
- and V is carbobenzyloxy, 2-chlorocarbobenzyloxy, 2-bromocarbobenzyloxy, dichlorocarbobenzyloxy or trifluoroacetyl.
A peptide having the structure:
- ##STR28## in which TFA is trifluoroacetyl.
A resin peptide having the structure:
- NH.sub.2 --Pro--Asn--CH.sub.2 -- R
- in which
- R is a crosslinked polystyrene resin.
A resin peptide having the structure:
- ##STR29## in which R is a crosslinked polystyrene resin,
- and Y is H or Bz.
A resin peptide having the structure:
- ##STR30## in which R is a crosslinked polystyrene resin, Bz is benzyl, p-methoxybenzyl, p-chlorobenzyl, p-nitrobenzyl or benzhydryl,
- Y is H or Bz,
- T is tosyl or nitro,
- W is carbobenzyloxy, tosyl, dinitrophenyl, Bz or H, and
- V is carbobenzyloxy, 2-chlorocarbobenzyloxy, 2-bromocarbobenzyloxy, dichlorocarbobenzyloxy or trifluoroacetyl.
A peptide having the structure:
- ##STR31## in which TFA is trifluoroacetyl.
In a process for synthesizing a resin peptide, the step of coupling L-Pro-P with the reactant
- NH.sub.2 --Asn--CH.sub.2 -- R
- or an active ester or an azide thereof, said coupling being conducted in the presence of a diimide unless said reactant is an active ester or an azide.
Dependencies are inferred from the claim text.