The Synthesis of Hadacidin: Sodium Cyanoborohydride Reduction of ?-Oximinoic Acids

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Abstract
The natural product Hadacidin (N-formyl-N-hydroxy-glycine) has been isolated from various fungi and was found to inhibit the growth of bacteria, tumor cells, and plant and animal tissue1. Specifically, the drug has been shown to be an inhibitor of adenylosuccinate synthetase, consequently blocking purine synthesis de novo as well as purine salvage via either the purine nucleoside cycle or hypoxanthine salvage. Due to this inhibitory activity hadacidin was studied as a chemotherapeutic agent; however, it was found to be only weakly active against various carcinomas2 and therefore has not been made commercially available. There is a current resurgence of interest in the drug due to its ability to affect the growth and development of various organs and organisms in a very specific manner3. This communication presents a simple and rapid synthetic route to the naturally occurring antibiotic, that may find general applicability in the synthesis of a variety of N-hydroxylated amino acid compounds which are important cell metabolites, often imp1icated in carci nogenesis.

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