Open AccessMicrobial transformation of N-methylcolchiceinamide
Author(s) -
Patrick J. Davis
Publication year - 1981
Publication title -
antimicrobial agents and chemotherapy
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.07
H-Index - 259
eISSN - 1070-6283
pISSN - 0066-4804
DOI - 10.1128/aac.19.3.465
Subject(s) - streptomyces griseus , metabolite , streptomycetaceae , microorganism , metabolism , streptomyces , alkylation , biotransformation , substrate (aquarium) , chemistry , colchicine , biochemistry , transformation (genetics) , actinomycetales , stereochemistry , chromatography , biology , bacteria , enzyme , ecology , genetics , gene , catalysis
Seventy-seven microorganisms were examined for their ability to metabolize the antineoplastic agent N-methylcolchiceinamide, an analog of colchicine. Five streptomycetes exhibited significant metabolism, and Streptomyces griseus NRRL B-599 completely converted the substrate to three metabolites. In preparative-scale studies, N-dealkylation resulted in the production of colchiceinamide, the major metabolite (65%), which was characterized by chemical, spectroscopic, and chromatographic comparisons with the standard compound. Two phenolic metabolites resulting from )-dealkylation were also isolated and identified as 2 and 3-O-demethyl-N-methylcolchiceinamide.