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

Kevin C. Potter | Zendy; Meirong Jia | Zendy; Young J. Hong | Zendy; Dean J. Tantillo | Zendy; Reuben J. Peters | Zendy

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

Author(s) -

Kevin C. Potter,

Meirong Jia,

Young J. Hong,

Dean J. Tantillo,

Reuben J. Peters

Publication year - 2016

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.6b00181

Subject(s) - chemistry , residue (chemistry) , deprotonation , oryza sativa , atp synthase , stereochemistry , biochemistry , enzyme , organic chemistry , ion , gene

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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