Document Detail

Algal pheromone biosynthesis: stereochemical analysis and mechanistic implications in gametes of Ectocarpus siliculosus.
MedLine Citation:
PMID:  20504036     Owner:  NLM     Status:  MEDLINE    
During sexual reproduction, female gametes or eggs of brown algae release pheromones to attract their male mating partners. The biologically active compounds comprise linear or alicyclic unsaturated hydrocarbons derived from the aliphatic terminus of C(20) polyunsaturated fatty acids (PUFAs) by oxidative cleavage. The current study addresses the stereochemical course of the pheromone biosynthesis using female gametes of the marine brown alga E. siliculosus and chiral deuterium-labeled arachidonic acids. The biosynthetic sequence is likely to proceed via an intermediary 9-hydroperoxyarachidonic acid, which is cleaved with loss of the C(16)-H(R) into the C(11)-hydrocarbon dictyopterene C and 9-oxonona-(5Z,7E)-dienoic acid.
Fabio Rui; Wilhelm Boland
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  75     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2010 Jun 
Date Detail:
Created Date:  2010-06-11     Completed Date:  2010-09-17     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  3958-64     Citation Subset:  IM    
Max Planck Institute for Chemical Ecology, Department of Bioorganic Chemistry, Hans-Knöll-Strasse 8, D-07745 Jena, Germany.
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MeSH Terms
Algae, Brown / chemistry,  genetics,  metabolism*
Germ Cells / metabolism*
Leukotrienes / chemistry
Molecular Structure
Pheromones / biosynthesis*
Reg. No./Substance:
0/Leukotrienes; 0/Pheromones; 67675-13-2/12-HPETE

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