Premium
Conformational aspects of polypeptide structure XIV. Synthesis of L ‐glutamate oligomers via active ester and azide coupling reactions
Author(s) -
Goodman Murray,
Rosen Ira G.,
Safdy Max
Publication year - 1964
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.360020602
Subject(s) - chemistry , dipeptide , azide , combinatorial chemistry , hydrazine (antidepressant) , catalysis , coupling reaction , solvent , organic chemistry , amino acid , biochemistry , chromatography
In this paper we have once again shown the general utility of the modified active ester synthesis using a dipeptide active ester. We have also demonstrated that the acyl azide coupling method using the modifications of Rudinger and Honzl, and Schwyzer make a good general method for the synthesis of complex oligopeptides. This method employs reactions known to give products of high optical purity in reasonable yields. The use of the t ‐butyloxycarbonyl hydrazyl (CBH) blocking group provides a good route to hydrazides of esters of glutamic acid. The classical route to prepare hydrazides involves the displacement of an ester with hydrazine. Such a pathway is clearly impossible because of the γ‐esters. Finally we demonstrated that trifluoroethanol is an excellent solvent for catalytic hydrogenation reactions.