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

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Date
2012-07-01
Authors
Zu, Liansuo
Xu, Meimei
Peters, Reuben
Lodewyk, Michael
Cane, David
Peters, Reuben
Tantillo, Dean
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Biochemistry, Biophysics and Molecular Biology
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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