Nitrogen-Nitrogen Bond Containing Antibiotics: Biosynthesis of Streptozocin

Abstract

The structures and properties of approximately 20 antibiotics from Streptomycetes as well as other microorganisms and of another 20 metabolites from bacteria, mushrooms, and plants which contain a nitrogen-nitrogen bond were recently reviewed by LaRue (1977). The physiological activities of these compounds comprise antitumor, cytotoxic, carcinogenic, and diabetogenic activities, but, despite the pharmacologic interest in these compounds, only scanty information is available on their biosynthesis and none on the enzymology and genetics of the formation of their nitrogen-nitrogen bonds. Our interest in the biosynthetic capabilities of Streptomycetes in general and a particular interest in the unexplored area of biological nitrogen-nitrogen bond formation prompted us to undertake biosynthetic studies on the antibiotic streptozocin and to initiate such studies with the antibiotic N-acetyl-6-diazo-5-oxo-L-norleucine (N-acetyl DON).