Enediyne polyketide synthases stereoselectively reduce the β-ketoacyl intermediates to β-D-hydroxyacyl intermediates in enediyne core biosynthesis

Org Lett. 2014 Aug 1;16(15):3958-61. doi: 10.1021/ol501767v. Epub 2014 Jul 14.

Abstract

PKSE biosynthesizes an enediyne core precursor from decarboxylative condensation of eight malonyl-CoAs. The KR domain of PKSE is responsible for iterative β-ketoreduction in each round of polyketide chain elongation. KRs from selected PKSEs were investigated in vitro with β-ketoacyl-SNACs as substrate mimics. Each of the KRs reduced the β-ketoacyl-SNACs stereoselectively, all affording the corresponding β-D-hydroxyacyl-SNACs, and the catalytic efficiencies (k(cat)/K(M)) of the KRs increased significantly as the chain length of the β-ketoacyl-SNAC substrate increases.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Enediynes / chemical synthesis*
  • Enediynes / chemistry
  • Molecular Structure
  • Polyketide Synthases / metabolism*
  • Polyketides / chemistry
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Enediynes
  • Polyketides
  • Polyketide Synthases