Biosynthesis of versipelostatin: identification of an enzyme-catalyzed [4+2]-cycloaddition required for macrocyclization of spirotetronate-containing polyketides.
J Am Chem Soc, 2015/1/21;137(2):572-5.
Hashimoto T[1], Hashimoto J, Teruya K, Hirano T, Shin-ya K, Ikeda H, Liu HW, Nishiyama M, Kuzuyama T
Affiliations
PMID: 25551461DOI: 10.1021/ja510711x
Impact factor: 16.383
Abstract
Versipelostatin (VST) is an unusual 17-membered macrocyclic polyketide product that contains a spirotetronate skeleton. In this study, the entire VST biosynthetic gene cluster (vst) spanning 108 kb from Streptomyces versipellis 4083-SVS6 was identified by heterologous expression using a bacterial artificial chromosome vector. Here, we demonstrate that an enzyme, VstJ, catalyzes the stereoselective [4+2]-cycloaddition between the conjugated diene and the exocyclic olefin of a newly identified tetronate-containing intermediate to form the spirotetronate skeleton during VST biosynthesis.
MeSH terms
Biocatalysis; Cycloaddition Reaction; Macrolides; Multigene Family; Oligosaccharides; Polyketides; Spiro Compounds; Stereoisomerism; Streptomyces; Substrate Specificity
More resources
Full text:
Europe PubMed Central; PubMed Central
EndNote: Download