Labeling Studies Clarify the Committed Step in Bacterial Gibberellin Biosynthesis

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• 作者：Ryan S. Nett ; Jeroen S. Dickschat ; Reuben J. Peters
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：December 2, 2016
• 年：2016
• 卷：18
• 期：23
• 页码：5974-5977
• 全文大小：307K
• ISSN：1523-7052

文摘

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.