Effect of Isotopically Sensitive Branching on Product Distribution for Pentalenene Synthase: Support for a Mechanism Predicted by Quantum Chemistry

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2012-07-01
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Zu, Liansuo
Xu, Meimei
Lodewyk, Michael
Cane, David
Tantillo, Dean
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Peters, Reuben
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Abstract

Mechanistic proposals for the carbocation cascade reaction leading to the tricyclic sesquiterpene pentalenene are assessed in light of the results of isotopically sensitive branching experiments with the H309A mutant of pentalenene synthase. These experimental results support a mechanism for pentalenene formation involving a 7-protoilludyl cation whose intermediacy was first predicted using quantum-chemical calculations.

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Reprinted with permission from Journal of the American Chemical Society 134 (2012): 11369, doi:10.1021/ja3043245. Copyright 2012 American Chemical Society.

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Sun Jan 01 00:00:00 UTC 2012
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