Journal
TETRAHEDRON
Volume 56, Issue 5, Pages 693-701Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(99)01060-1
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The final steps in the biosynthesis of the antifungal peptidyl-nucleoside blasticidin S (3) have been revised to include a novel self-resistance mechanism wherein the previously proposed final precursor, demethylblasticidin S (7), is modified with a leucine residue yielding leucyldemethylblasticidin S (10) which exhibits reduced antibiotic activity. Methylation of 10 yields leucylblasticidin S (9) which can be exported from the bacterium and hydrolyzed to 3. Also disclosed is the finding of a blasticidin S N-acetyltransferase activity that may function to detoxify 3 and 7 inadvertently produced prior to export or which gain reentry to the cell. (C) 2000 Elsevier Science Ltd. All rights reserved.
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