Total synthesis and antifungal activity of a carbohydrate ring-expanded pyranosyl nucleoside analogue of nikkomycin B

Christina S. Stauffer, Pushpal Bhaket, Annette W. Fothergill, Michael G. Rinaldi, Apurba Datta

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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 languageEnglish (US)
Pages (from-to)9991-9997
Number of pages7
JournalJournal of Organic Chemistry
Volume72
Issue number26
DOIs
StatePublished - Dec 21 2007

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ASJC Scopus subject areas

  • Organic Chemistry

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