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- Title
Blocking Deprotonation with Retention of Aromaticity in a Plant ent-Copalyl Diphosphate Synthase Leads to Product Rearrangement.
- Authors
Potter, Kevin C.; Zi, Jiachen; Hong, Young J.; Schulte, Samuel; Malchow, Brandi; Tantillo, Dean J.; Peters, Reuben J.
- Abstract
Substitution of a histidine, comprising part of the catalytic base group in the ent-copalyl diphosphate synthases found in all seed plants for gibberellin phytohormone metabolism, by a larger aromatic residue leads to rearrangements. Through a series of 1,2-hydride and methyl shifts of the initially formed bicycle predominant formation of (-)-kolavenyl diphosphate is observed. Further mutational analysis and quantum chemical calculations provide mechanistic insight into the basis for this profound effect on product outcome.
- Subjects
PROTON transfer reactions; HISTIDINE; CATALYSIS research; GIBBERELLINS; PLANT hormone metabolism; QUANTUM chemistry
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 2, p634
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201509060