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Labeling Studies Clarify the Committed Step in Bacterial Gibberellin Biosynthesis

Author:
Nett, Ryan S., Dickschat, Jeroen S., Peters, Reuben J.
Source:
Organic letters 2016 v.18 no.23 pp. 5974-5977
ISSN:
1523-7052
Subject:
bacteria, biosynthesis, carbon, chemical reactions, chemical structure, cytochrome P-450, extrusion, fungi, gibberellins, isotope labeling, nuclear magnetic resonance spectroscopy, plant hormones, plants (botany), stable isotopes
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.
Agid:
5792118