Microbial production of vitamin B12 antimetabolites: II. 2-Amino-4-keto-3-methylpentanoic acids from bacillus cereus 439 |
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Authors: | D Perlman KL Perlman M Bodanszky A Bodanszky RL Foltz HW Matthews |
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Institution: | 1. School of Pharmacy, University of Wisconsin, Madison, Wisconsin, USA;2. Department of Chemistry, Case Western Reserve University, Cleveland, Ohio, USA;3. Battelle''s Columbus Laboratories, Columbus, Ohio, USA |
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Abstract: | 2-Amino-4-keto-3-methylpentanoic acids were isolated as a diastereomeric mixture from Bacillus cereus 439 fermentations and found to be vitamin B12 antimetabolites in a bioassay system based on the vitamin B12-requiring Escherichia coli (Davis 113-3). A similar diastereomeric mixture with bioactivity was synthesized by condensation of 2-bromo-3-butanone with sodio diethyl acetamidomalonate followed by hydrolysis with 6 N HCl and purification by ion-exchange chromatography. The growth inhibitory effects of the antimetabolite were reversed by vitamin B12, l-methionine, l-isoleucine, l-leucine, l-valine, and d-alanine. |
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