Document Type
Article
Publication Date
2012
Journal or Book Title
Organic Letters
Volume
14
Issue
23
First Page
5828
Last Page
5831
DOI
10.1021/ol3026022
Abstract
Class II diterpene cyclases catalyze bicyclization of geranylgeranyl diphosphate. While this reaction typically is terminated via methyl deprotonation to yield copalyl diphosphate, in rare cases hydroxylated bicycles are produced instead. Abietadiene synthase is a bifunctional diterpene cyclase that usually produces a copalyl diphosphate intermediate. Here it is shown that substitution of aspartate for a conserved histidine in the class II active site of abietadiene synthase leads to selective production of 8α-hydroxy-CPP instead, demonstrating striking plasticity.
Rights
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Copyright Owner
American Chemical Society
Copyright Date
2012
Language
en
File Format
application/pdf
Recommended Citation
Criswell, Jared; Potter, Kevin; Shephard, Freya; Beale, Michael H.; and Peters, Reuben J., "A Single Residue Change Leads to a Hydroxylated Product from the Class II Diterpene Cyclization Catalyzed by Abietadiene Synthase" (2012). Biochemistry, Biophysics and Molecular Biology Publications. 4.
https://lib.dr.iastate.edu/bbmb_ag_pubs/4
Included in
Biochemistry, Biophysics, and Structural Biology Commons, Natural Products Chemistry and Pharmacognosy Commons
Comments
Reprinted (adapted) with permission from Organic Letters 14 (2012): 5828, doi:10.1021/ol3026022. Copyright 2012 American Chemical Society.