Abstract
The Streptomyces-derived nikkomycins are a unique class of peptidyl nucleoside natural products, with potent antifungal activity against a variety of pathogenic fungi. In continuation of our structure-activity relationship studies on the nikkomycins, this paper describes the strategic design, synthesis and biological evaluation of a 'doubly modified' generation of nikkomycin analogs. The structural modifications included a ring-expanded carbohydrate core and a simplified peptidyl side chain. Biological screening of these novel analogs against clinical isolates of various human pathogenic fungi indicated that the described modifications of the structural features of nikkomycin could be a potentially beneficial strategy towards optimizing the antifungal potency of this class of peptidyl nucleoside antibiotics. Continued investigation of the pyranosyl nikkomycin analogs is warranted to fully explore and optimize the structural features of this novel lead for the desired development of a new class of therapeutically useful antifungal drugs.
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