Bacterial Degradation of Biotin and Dethiobiotin: Isolation and Identification of β-Hydroxy and Keto Metabolites

Abstract

The degradation of biotin and dethiobiotin by resting cells of a biotin-degrading bacterium, Mycoplana sp. No. 166, was studied. The metabolites were isolated from reaction mixtures supplemented with biotin or dethiobiotin. By mass and NMR spectral analyses, the hiotin metabolites were identified to be bisnorbiotin and β-hydroxybisnorbiotin, and the dethiobiotin metabolites to be methyl tetranordethiobiotinyl ketone, bisnordethiobiotin, β-hydroxybisnordethiobiotin, and tetranordethiobiotin. The two β-hydroxy metabolites and the keto metabolite were new compounds.