A CONVENIENT DEGRADATION OF POLYOXIN D TO URACIL POLYOXIN-C - ACCESS TO KEY INTERMEDIATES AND SYNTHESIS OF ANTIFUNGAL ALPHA-AMINOACYL DERIVATIVES OF UPOC

Authors
COOPER AB DESAI J LOVEY RG SAKSENA AK GIRIJAVALLABHAN VM GANGULY AK LOEBENBERG D PARMEGIANI R CACCIAPUOTI A
Citation
Ab. Cooper et al., A CONVENIENT DEGRADATION OF POLYOXIN D TO URACIL POLYOXIN-C - ACCESS TO KEY INTERMEDIATES AND SYNTHESIS OF ANTIFUNGAL ALPHA-AMINOACYL DERIVATIVES OF UPOC, Bioorganic & medicinal chemistry letters, 3(6), 1993, pp. 1079-1084
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
3
Issue
6
Year of publication
1993
Pages
1079 - 1084
Database
ISI
SICI code
0960-894X(1993)3:6<1079:ACDOPD>2.0.ZU;2-J
Abstract
A convenient degradation of readily available polyoxin D under Edman c onditions gave carboxyuracil polyoxin C 3 in high yield. Decarboxylati on to uracil polyoxin C 5 (UPOC) and ring contraction to imidazolone c ompound 8, gave important nikkomycin Z and X intermediates respectivel y. Syntheses of new polyoxin/nikkomycin analogs 12-27, some with excel lent chitin synthetase inhibition and Candida albicans whole cell acti vity are described. The importance of beta-methyl substituted amino ac id side chains for whole cell activity is highlighted.