Mutational biosynthesis of a FK506 analogue containing a non-natural starter unit

Mol Biosyst. 2013 May;9(5):944-7. doi: 10.1039/c2mb25419k.

Abstract

A FK506 analogue containing a non-natural starter unit was obtained through mutasynthesis by feeding cultures of Streptomyces sp. KCTC 11604BP fkbO deletion mutant with 3-cyclohexene-1-carboxylic acid. The structure of the new compound, 32-dehydroxy-FK506, and its biological activities were determined.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biosynthetic Pathways
  • Chorismic Acid / chemistry
  • Chorismic Acid / metabolism
  • Chromatography, High Pressure Liquid
  • Cyclohexanecarboxylic Acids / chemistry
  • Cyclohexanecarboxylic Acids / metabolism
  • Cyclohexenes / chemistry
  • Cyclohexenes / metabolism
  • Models, Chemical
  • Molecular Structure
  • Mutation*
  • Oxo-Acid-Lyases / genetics
  • Oxo-Acid-Lyases / metabolism
  • Plant Proteins / genetics
  • Plant Proteins / metabolism
  • Spectrometry, Mass, Electrospray Ionization
  • Streptomyces / genetics*
  • Streptomyces / metabolism*
  • Tacrolimus / analogs & derivatives
  • Tacrolimus / chemistry
  • Tacrolimus / metabolism*
  • Tandem Mass Spectrometry

Substances

  • Cyclohexanecarboxylic Acids
  • Cyclohexenes
  • Plant Proteins
  • 3-cyclohexene-1-carboxylic acid
  • Oxo-Acid-Lyases
  • chorismate pyruvate lyase
  • Chorismic Acid
  • Tacrolimus