Product Rearrangement from Altering a Single Residue in the Rice syn-Copalyl Diphosphate Synthase

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2016-01-01
Authors
Potter, Kevin
Jia, Meirong
Peters, Reuben
Hong, Young
Tantillo, Dean
Peters, Reuben
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Through site-directed mutagenesis targeted at identification of the catalytic base in the rice (Oryza sativa) syn-copalyl diphosphate synthase OsCPS4, changes to a single residue (H501) were found to induce rearrangement rather than immediate deprotonation of the initially formed bicycle, leading to production of the novel compound syn-halimadienyl diphosphate. These mutational results are combined with quantum chemical calculations to provide insight into the underlying reaction mechanism.

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<p>This article is published as Product Rearrangement from Altering a Single Residue in the Rice syn-Copalyl Diphosphate Synthase, Kevin C. Potter, Meirong Jia, Young J. Hong, Dean Tantillo, and Reuben J. Peters, Organic Letters <strong>2016</strong> <em>18</em> (5), 1060-1063, DOI: <a href="http://dx.doi.org/10.1021/acs.orglett.6b00181" target="_blank">10.1021/acs.orglett.6b00181</a>. Posted with permission.</p>
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