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4‐(Dimethylamino)pyridine N ‐oxide (DMAPO): An Effective Nucleophilic Catalyst in the Peptide Coupling Reaction with 2‐Methyl‐6‐nitrobenzoic Anhydride
Author(s) -
Shiina Isamu,
Ushiyama Hisaya,
Yamada Yoko,
Kawakita Yoichi,
Nakata Kenya
Publication year - 2008
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200700305
Subject(s) - racemization , chemistry , catalysis , nucleophile , pyridine , pyridine n oxide , peptide , peptide synthesis , amino acid , medicinal chemistry , oligopeptide , coupling reaction , organic chemistry , diketopiperazines , stereochemistry , combinatorial chemistry , biochemistry
Various carboxamides or peptides were synthesized from the corresponding carboxylic acids and amines or α‐amino acids in high yields by the catalysis of 4‐(dimethylamino)pyridine N ‐oxide (DMAPO) with 2‐methyl‐6‐nitrobenzoic anhydride (MNBA). Because the segment‐coupling reaction of α‐amino acids proceeds through the effective activation of the carboxylic acid moieties with DMAPO in the presence of tertiary amines under mild conditions, undesired racemization was hardly observed in the synthesis of oligopeptides such as Z‐Gly‐Phe‐Val‐OMe, Z‐Phe‐Val‐Ala‐OMe, and Bz‐Val‐Val‐OMe.