Premium
Synthesis of sequential polypeptides containing L ‐β‐3,4‐dihydroxyphenyl‐α‐alanine (DOPA) and L ‐glutamic acid
Author(s) -
Yamamoto Hiroyuki,
Hayakawa Tadao
Publication year - 1979
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.1979.360181212
Subject(s) - chemistry , side chain , chloroform , monomer , alanine , stereochemistry , glutamic acid , amino acid , organic chemistry , biochemistry , polymer
Sequential polypeptides with the repeating units L ‐glutamyl‐ L ‐DOPA, L ‐DOPA‐ L ‐glutamyl‐ L ‐DOPA, L ‐glutamyl‐ L ‐glutamyl‐ L ‐DOPA, L ‐DOPA‐ L ‐DOPA‐ L ‐glutamyl‐ L ‐DOPA, and L ‐glutamyl‐ L ‐glutamyl‐ L ‐glutamyl‐ L ‐DOPA have been synthesized by solution polymerization of the p ‐nitrophenyl esters of the corresponding di‐, tri‐, and tetrapeptides. The O, O′‐dimethyl and γ‐methyl groups were used to protect side chains of L ‐DOPA and L ‐glutamic acid. The monomers for the polytripeptides and polytetrapeptides were prepared by stepwise elongation, using the dicyclohexylcarbodiimide coupling method. Moderately high molecular weight sequential polypeptides were obtained. The protected groups of the side chain were removed simultaneously by use of boron tribromide in chloroform. Trimethylphosphate‐soluble sequential polypeptides containing L ‐DOPA were obtained.