- Biosynthesis of 9-methylstreptimidone involves a new decarboxylative step for polyketide terminal diene formation.
Biosynthesis of 9-methylstreptimidone involves a new decarboxylative step for polyketide terminal diene formation.
Organic letters (2013-02-27)
Bo Wang, Yongxiang Song, Minghe Luo, Qi Chen, Junying Ma, Hongbo Huang, Jianhua Ju
PMID23438151
ABSTRACT
9-Methylstreptimidone is a glutarimide antibiotic showing antiviral, antifungal, and antitumor activities. Genome scanning, bioinformatics analysis, and gene inactivation experiments reveal a gene cluster responsible for the biosynthesis of 9-methylstreptimidone in Streptomyces himastatinicus. The unveiled machinery features both acyltransferase- and thioesterase-less iterative use of module 5 as well as a branching module for glutarimide generation. Impressively, inactivation of smdK leads to a new carboxylate analogue unveiling a new mechanism for polyketide terminal diene formation.