Labeling Studies Clarify the Committed Step in Bacterial Gibberellin Biosynthesis

被引：12

作者：

Nett, Ryan S. ^{[1
]}

Dickschat, Jeroen S. ^{[2
]}

Peters, Reuben J. ^{[1
]}

机构：

[1] Iowa State Univ, Roy J Carver Dept Biochem Biophys & Mol Biol, Ames, IA 50011 USA

[2] Rhein Friedrich Wilhelms Univ Bonn, Kekule Inst Organ Chem & Biochem, Gerhard Domagk Str 1, D-53121 Bonn, Germany

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 23期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

KAURENOIC ACID OXIDASE; PATHWAY; FUJIKUROI; GENE; REARRANGEMENT; ENCODES; SYSTEM; COLI;

D O I：

10.1021/acs.orglett.6b02569

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bacteria have evolved gibberellin phytohormone biosynthesis independently of plants and fungi. Through C-13-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-4 alpha carboxylate proximity.

引用

页码：5974 / 5977

页数：4

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