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PMID: 18052062 Published · ppublish English Journal Article Research Support, N.I.H., Extramural

A single residue switch converts abietadiene synthase into a pimaradiene specific cyclase.

Journal of the American Chemical Society ·Vol. 129 ·No. 51 ·2007-12-26 ·Pages 15736-7

Wilderman PR, Peters RJ

Abstract

Terpene synthases often catalyze complex cyclization reactions that typically represent the committed step in particular biosynthetic pathways, leading to great interest in their enzymatic mechanisms. We have recently demonstrated that substitution of a specific Ile with Thr was sufficient to "short circuit" the complex cyclization reaction normally catalyzed by ent-kaurene synthases to instead produce ent-pimaradiene. Here we report that the complex cyclization/rearrangement reaction catalyzed by abietadiene synthase can be similarly cut short to produce pimaradienes by an analogous Ser for Ala change, albeit with a slight shift in active site location to accommodate the difference in substrate stereochemistry. This result has mechanistic implications for enzymatic catalysis of abietadiene cyclization, and terpene synthases more broadly. Furthermore, these defined single residue switches may be useful in engineering product outcome in diterpene synthases more generally.

MeSH Terms
Catalysis Cyclization Diterpenes/metabolism Isomerases/chemistry Stereoisomerism
Chemicals
Diterpenes Isomerases abietadiene cyclase
Authors & Affiliations
2 authors, click to expand affiliations / ORCID
Wilderman P Ross
Department of Biochemistry, Biophysics, and Molecular Biology, Iowa State University, Ames, Iowa 50011, USA.
Peters Reuben J
References (13)
13 references, click to expand
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Article Info
Journal
Journal of the American Chemical Society
Abbr.
J Am Chem Soc
ISSN
1520-5126
Published
2007-12-26
Epub
2007-00-01
Pages
15736-7
Language
English
Region
United States
NLM ID
7503056
PMCID
PMC2525807
Subset
IM
Grants
NIGMS NIH HHS · R01 GM076324 · United States
NIGMS NIH HHS · R01 GM076324-02 · United States
NIGMS NIH HHS · GM076324 · United States
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