Abstract
(Chemical Equation Presented) In a study aimed at investigating an as yet unknown structure-activity relationship of the nikkomycin family of antifungal peptidyl nucleoside antibiotics, the present research reports the synthesis and antifungal evaluation of a carbohydrate ring-expanded pyranosyl nucleoside analogue of nikkomycin B. Employing a convergent synthetic route, independent synthesis of the N-terminal amino acid side chain and a stereoselective de novo construction of the desired pyranosyl nucleoside amino acid fragment was followed by peptidic coupling of the two components, leading to the first synthesis of a carbohydrate ring-enlarged pyranosyl nikkomycin B analogue. In vitro biological evaluation of the above analogue against a variety of human pathogenic fungi demonstrated significant antifungal activity against several fungal strains of clinical significance.
Original language | English (US) |
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Pages (from-to) | 9991-9997 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 72 |
Issue number | 26 |
DOIs | |
State | Published - Dec 21 2007 |
ASJC Scopus subject areas
- Organic Chemistry