Labeling Studies Clarify the Committed Step in Bacterial Gibberellin Biosynthesis

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2016-01-01
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Nett, Ryan
Nett, Ryan
Dickschat, Jeroen
Peters, Reuben
Peters, Reuben
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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.

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<p>Reprinted (adapted) with permission from Labeling Studies Clarify the Committed Step in Bacterial Gibberellin Biosynthesis. Ryan S. Nett, Jeroen S. Dickschat, and Reuben J. Peters. Organic Letters <strong>2016</strong> <em>18</em> (23), 5974-5977. DOI: <a href="http://dx.doi.org/Labeling%20Studies%20Clarify%20the%20Committed%20Step%20in%20Bacterial%20Gibberellin%20Biosynthesis%20Ryan%20S.%20Nett,%20Jeroen%20S.%20Dickschat,%20and%20Reuben%20J.%20Peters%20Organic%20Letters%202016%2018%20(23),%205974-5977%20DOI:%2010.1021/acs.orglett.6b02569" target="_blank">10.1021/acs.orglett.6b02569</a>. Copyright 2016 American Chemical Society.</p>
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