ANTIFUNGAL LIPOPEPTIDES - STRUCTURE-ACTIVITY-RELATIONSHIPS OF 3-HYDROXYGLUTAMINE-MODIFIED PNEUMOCANDIN B-0 DERIVATIVES

Authors
ZAMBIAS RA JAMES C HAMMOND ML ABRUZZO GK BARTIZAL KF NOLLSTADT KH DOUGLAS C MARRINAN J BALKOVEC JM
Citation
Ra. Zambias et al., ANTIFUNGAL LIPOPEPTIDES - STRUCTURE-ACTIVITY-RELATIONSHIPS OF 3-HYDROXYGLUTAMINE-MODIFIED PNEUMOCANDIN B-0 DERIVATIVES, Bioorganic & medicinal chemistry letters, 5(20), 1995, pp. 2357-2362
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
5
Issue
20
Year of publication
1995
Pages
2357 - 2362
Database
ISI
SICI code
0960-894X(1995)5:20<2357:AL-SO3>2.0.ZU;2-#
Abstract
Selective methanolysis or dehydration followed by reduction of the 3-h ydroxyglutamine residue of pneumocandin B-0 (1) or its dideoxy analog 5 (L-692,289) gave the methyl 3-hydroxyglutamate and 3-hydroxyornithin e analogs 6 and 9, respectively. Further derivatization of these analo gs allowed a study of the SAR at this position. In general, carboxylic acid-containing derivatives were poorer antifungal agents than neutra l derivatives while amine-bearing analogs displayed the greatest poten cy.