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The Fate of Molecular Oxygen in Azinomycin Biosynthesis
Gilbert T Kelly1, Lauren A Washburn1, Coran M H Watanabe1
1Department of Chemistry , Texas A&M University , College Station , Texas 77843 , United States.
Abstract:
The azinomycins are a family of aziridine-containing antitumor antibiotics and represent a treasure trove of biosynthetic reactions. The formation of the azabicyclo[3.1.0]hexane ring and functionalization of this ring system remain the least understood aspects of the pathway. This study reports the incorporation of 18O-labeled molecular oxygen in azinomycin biosynthesis including both oxygens of the diol that ultimately adorn the aziridino[1,2- a]pyrrolidine moiety. Likewise, two other sites of heavy atom incorporation are observed.
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