PNEUMOCANDIN ANTIFUNGAL LIPOPEPTIDES - THE PHENOLIC HYDROXYL IS REQUIRED FOR 1,3-BETA-GLUCAN SYNTHESIS INHIBITION

Authors
BALKOVEC JM BLACK RM ABRUZZO GK BARTIZAL K DREIKORN S NOLLSTADT K
Citation
Jm. Balkovec et al., PNEUMOCANDIN ANTIFUNGAL LIPOPEPTIDES - THE PHENOLIC HYDROXYL IS REQUIRED FOR 1,3-BETA-GLUCAN SYNTHESIS INHIBITION, Bioorganic & medicinal chemistry letters, 3(10), 1993, pp. 2039-2042
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
3
Issue
10
Year of publication
1993
Pages
2039 - 2042
Database
ISI
SICI code
0960-894X(1993)3:10<2039:PAL-TP>2.0.ZU;2-N
Abstract
Pneumocandin B-0 1 undergoes selective oxidation/reduction chemistry a t the homotyrosine (hty) residue. Removal of the phenolic hydroxyl giv es >140-fold loss in activity against a Candida albicans 1,3-beta-gluc an synthetase enzyme preparation and a significant loss of antifungal activity. Inversion of the C4-hty hydroxyl causes about a 70-fold decr ease in potency, while removal of this hydroxyl yields a more potent i nhibitor.