Labeling Studies Clarify the Committed Step in Bacterial Gibberellin Biosynthesis

Org Lett. 2016 Dec 2;18(23):5974-5977. doi: 10.1021/acs.orglett.6b02569. Epub 2016 Nov 21.

Abstract

Bacteria have evolved gibberellin phytohormone biosynthesis independently of plants and fungi. Through 13C-labeling and NMR analysis, the mechanistically unusual "B" ring contraction catalyzed by a cytochrome P450 (CYP114), which is the committed step in gibberellin biosynthesis, was shown to occur via oxidative extrusion of carbon-7 from ent-kaurenoic acid in bacteria. This is identical to the convergently evolved chemical transformation in plants and fungi, suggesting a common semipinacol rearrangement mechanism potentially guided by carbon-4α carboxylate proximity.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Bacteria / chemistry*
  • Bacteria / metabolism
  • Cytochrome P-450 Enzyme System / metabolism*
  • Gibberellins / biosynthesis*
  • Gibberellins / chemistry
  • Molecular Conformation

Substances

  • Gibberellins
  • Cytochrome P-450 Enzyme System