A FAST PROCEDURE FOR THE PREPARATION OF AMIDES PEPTIDES FROM CARBOXYLIC-ACIDS AND AZIDES VIA 2 REDOX REACTIONS - APPLICATION TO THE SYNTHESIS OF METHIONINE-ENKEPHALIN/

Citation
Sk. Ghosh et al., A FAST PROCEDURE FOR THE PREPARATION OF AMIDES PEPTIDES FROM CARBOXYLIC-ACIDS AND AZIDES VIA 2 REDOX REACTIONS - APPLICATION TO THE SYNTHESIS OF METHIONINE-ENKEPHALIN/, Bulletin of the Chemical Society of Japan, 69(6), 1996, pp. 1705-1711
Citations number
40
Categorie Soggetti
Chemistry
ISSN journal
00092673
Volume
69
Issue
6
Year of publication
1996
Pages
1705 - 1711
Database
ISI
SICI code
0009-2673(1996)69:6<1705:AFPFTP>2.0.ZU;2-B
Abstract
A one-pot self regulated approach for the synthesis of amides/peptides based on two reduction-oxidation (redox) reactions has been described . The primary and secondary amides/peptides are made by using azidotri methylsilane and alkyl azides/alpha-azido acid derivatives respectivel y as the direct source of amine components. Benzeneselenol, generated in the reaction medium during carboxyl activation, has been found to b e an effective reducing agent for the conversion of azides to primary amines. The methodology has been applied to the synthesis of methionin e enkephalin.