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Title

Sex pheromone biosynthetic pathway for disparlure in the gypsy moth, Lymantria dispar

AuthorsJurenka, Russell A.; Subchev, Mitko; Abad, José Luis CSIC ORCID ; Choi, Man-Yeon; Fabriàs, Gemma CSIC ORCID
KeywordsSex pheromone
Female moths
Biosynthetic pathway
Lymantria dispar
Issue Date17-Jan-2003
PublisherNational Academy of Sciences (U.S.)
CitationProceedings of the National Academy of Sciences of the USA 100(3): 809-814 (2003)
AbstractThe pheromone biosynthetic pathway for production of the sex pheromone disparlure, 2-methyl-7R,8S-epoxy-octadecane, was determined for the gypsy moth. Each step in the pathway was followed by using deuterium-labeled compounds that could be identified by using GC/MS. This approach provides unequivocal determination of specific reactions in the pathway. It was shown that the alkene precursor, 2-methyl-Z7-octadecene, is most likely made in oenocyte cells associated with abdominal epidermal cells. The pathway begins with valine contributing carbons for chain initiation, including the methyl-branched carbon, followed by chain elongation to 19 carbons. The double bond is introduced with an unusual Δ12 desaturase that utilizes a methyl-branched substrate. The resulting 18-methyl-Z12-nonadecenoate is decarboxylated to the hydrocarbon, 2-methyl-Z7-octadecene. The alkene is then transported to the pheromone gland through the hemolymph, most probably by lipophorin. At the pheromone gland, the alkene is unloaded and transformed into the epoxide disparlure for release into the environment. A chiral HPLC column was used to demonstrate that the (R,S)-stereoisomer of the epoxide, (+)-disparlure is found in pheromone glands.
Description6 pages, 7 figures.-- PMID: 12533665 [PubMed].-- PMCID: PMC298683.-- Printed version published Feb 4, 2003.-- Full text version available at: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC298683/?tool=pubmed
Publisher version (URL)http://dx.doi.org/10.1073/pnas.0236060100
URIhttp://hdl.handle.net/10261/20119
DOI10.1073/pnas.0236060100
ISSN0027-8424
E-ISSN1091-6490
Appears in Collections:(IQAC) Artículos

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