3-Amino-5-Hydroxybenzoic Acid in Antibiotic Biosynthesis. IX. The Status of Reduced Derivatives in Mitomycin Biosynthesis

Abstract

The addition of (methylene-²H₂)-3-amino-5-hydroxybenzyl alcohol (8) hydrochloride to growing cultures of Streptomyces verticillatus inhibits production of the mitomycin antibiotic porfiromycin (2) by the microorganism. No incorporation of deuterium into porfiromycin occurs, and the isotopic composition of the alcohol recovered from the fermentation is unchanged. The significance of these results with regard to the immediate metabolic precursors of 3-amino-5-hydroxybenzoic acid (3) and the reduction stages involved in the established conversion of this amino acid into mitomycins are discussed.