Premium
Stepwise synthesis of oligopeptides with N ‐carboxy α‐amino acid anhydrides. II. Oligopeptides with some polar side chains
Author(s) -
Katakai Ryoichi,
Oya Masanao,
Uno Keikichi,
Iwakura Yoshio
Publication year - 1971
Publication title -
biopolymers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.360101113
Subject(s) - chemistry , oligopeptide , side chain , amino acid , lysine , nucleophile , aspartic acid , racemization , polar , peptide synthesis , acetonitrile , stereochemistry , organic chemistry , peptide , biochemistry , catalysis , polymer , physics , astronomy
The reaction of NCA's with some amino acids having a nucleophilic functional group on the side chain was studied in a heterogeneous reaction medium (acetonitrile‐water). Glutamic acid and aspartic acid, having a free carboxyl group on the side chain, were successfully used to synthesize oligopeptides without interactions of the γ‐ and β‐carboxyl group with NCA's. Two products were obtained by the reaction of NCA with L ‐lysine, which contains a free amino group on the side chain. ε‐Protected lysine was used to prepare α‐peptides as a nucleophile in the reaction. No racemization was observed in the synthesis of peptides by the NCA method in the heterogeneous solvent system. Oligopeptides with some polar side chains were synthesized by the NCA method.