Microbial production of vitamin B12 antimetabolites. IV isolation and identification of 4-keto-5-amino-6-hydroxyhexanoic acid

Abstract

4-Keto-5-amino-6-hydroxyhexanoic acid was isolated from Bacillus cereus 102804 fermentations and found to inhibit the growth of Gram-positive and Gram-negative bacteria, when grown in a chemically defined medium. The mechanism appeared to be the inhibition of d- aminolevulinic acid dehydratase. The Ki value of 4-keto-5-amino-6-hydroxyhexanoic acid in an enzyme preparation of Propionibacterium shermanii was 0.72 μM. Similar test conditions with 4-keto-5-aminohexanoic acid resulted in a Ki of 12.1 μM. In both cases competitive inhibition was found. The structure of 4-keto-5-amino-6-hydroxyhexanoic acid was determined. © 1981, JAPAN ANTIBIOTICS RESEARCH ASSOCIATION. All rights reserved.