Stereocontrolled Synthesis of 5′- and 6′-Epimeric Analogues of Muraymycin Nucleoside Antibiotics

Abstract

Naturally occurring nucleoside antibiotics, for example, Streptomyces-produced muraymycins, represent a promising class of potential lead structures for the development of novel antimicrobial agents. The efficient preparation of muraymycin analogues is an essential prerequisite for detailed structure–activity relationship (SAR) studies, particularly with respect to the variation of the stereochemistry in a controlled manner. In this work, stereoselective syntheses of 5′- as well as 6′-epimers of muraymycins are reported. The obtained target structures also represent useful probes for the elucidation of the biosynthesis of muraymycins and related nucleoside antibiotics.

Key words

antibiotics - medicinal chemistry - natural products - ­nucleosides - biosynthesis

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