Nucleoside antibiotics are an exciting class of natural products that possess activity against a wide variety of bacterial pathogens. The sansanmycins belong to a subclass of nucleoside antibiotics called uridylpeptide natural products and were first isolated from a number of Streptomyces sp. between 2007 and 2010. They are comprised of a deoxy-uridine fragment linked to a pseudo-peptide unit via a unique cis-enamide bond. The sansanmycins were chosen as a target for total synthesis and for the preparation of structural analogues to facilitate a comprehensive structure-activity relationship (SAR) profile against Mycobacterium tuberculosis (Mtb). Efforts toward the total synthesis that focus on a novel means of constructing the deoxy uridine fragment and the enamide linkage will be described. A first generation library of dihydro-sansanmycin analogues have also been synthesised and tested against Mtb. Preliminary SAR data has identified structural features that are critical for antitubercular activity.

Synthesis and evaluation of sansanmycin analogs as antitubercular agents

248th National Meeting (2014)

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