Document Detail

Molecular mechanism of enzymatic allene oxide cyclization in plants.
MedLine Citation:
PMID:  18272375     Owner:  NLM     Status:  MEDLINE    
Jasmonates, a collective term combining both jasmonic acid (JA) and related derivatives, are ubiquitously distributed in the plant kingdom. They are characterized as lipid-derived signal molecules which mediate a plethora of physiological functions, in particular stress responses, male fertility, and a multitude of developmental processes. In the course of JA biosynthesis, the first oxylipin with signal character, cis-(+)-12-oxo-phytodienoic acid (OPDA), is produced in a cyclization reaction catalyzed by allene oxide cyclase (AOC). This enzyme-catalyzed ring closure is of particular importance, as it warrants the enantiomeric structure at the cyclopentenone ring which in the end results in the only bioactive JA enantiomer, cis-(+)-JA. In this review, we focus on the structural and molecular mechanisms underlying the above mentioned cyclization reaction. In this context, we will discuss the crystal structure of AOC2 of Arabidopsis thaliana with respect to putative binding sites of the instable substrate, 12,13-epoxy-9(Z),11,15(Z)-octadecatrienoic acid (12,13-EOT), as well as possible intermolecular rearrangements during the cyclization reaction.
Eckhard Hofmann; Stephan Pollmann
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Review     Date:  2007-12-31
Journal Detail:
Title:  Plant physiology and biochemistry : PPB / Société française de physiologie végétale     Volume:  46     ISSN:  0981-9428     ISO Abbreviation:  Plant Physiol. Biochem.     Publication Date:  2008 Mar 
Date Detail:
Created Date:  2008-03-24     Completed Date:  2008-07-21     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9882449     Medline TA:  Plant Physiol Biochem     Country:  France    
Other Details:
Languages:  eng     Pagination:  302-8     Citation Subset:  IM    
Biophysics, Department of Biology and Biotechnology, Ruhr-University Bochum, Universitaetsstrasse 150, D-44801 Bochum, Germany.
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MeSH Terms
Cyclopentanes / chemistry,  metabolism
Fatty Acids, Unsaturated / chemistry,  metabolism
Intramolecular Oxidoreductases / chemistry,  metabolism*
Linoleic Acid / chemistry*,  metabolism
Models, Chemical
Models, Molecular
Molecular Structure
Oxylipins / chemistry,  metabolism
Plant Proteins / chemistry,  metabolism*
Protein Structure, Tertiary
Reg. No./Substance:
0/Cyclopentanes; 0/Fatty Acids, Unsaturated; 0/Oxylipins; 0/Plant Proteins; 2197-37-7/Linoleic Acid; 67204-66-4/12-oxophytodienoic acid; 6894-38-8/jasmonic acid; EC 5.3.-/Intramolecular Oxidoreductases; EC isomerase

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