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Title

Synthesis and use of deuterated palmitic acids to decipher the cryptoregiochemistry of a Δ(13) desaturation

AuthorsAbad, José Luis CSIC ORCID ; Serra, Montserrat; Camps Díez, Francisco; Fabriàs, Gemma CSIC ORCID
KeywordsDeuterated palmitic acids
Cryptoregiochemistry
Sex pheromone
Issue Date6-Jan-2007
PublisherAmerican Chemical Society
CitationThe Journal of Organic Chemistry 72(3): 760-764 (2007)
AbstractThe synthesis of two hexadeuterated palmitic acids differing in the position of the diagnostic labels, and their use to decipher the cryptoregiochemistry of a Δ(13) desaturation are described. A dithiane and a triple bond functionalities were used to introduce the diagnostic (C13 or C14) and tagging (C8 and C9) labels, respectively, in the palmitic acid skeleton. Using these probes, the cryptoregiochemistry of the Δ(13) desaturation involved in the biosynthesis of Thaumetopoea pityocampa sex pheromone was studied by means of kinetic isotope effect determinations. Transformation of both (Z)-11-hexadecenoic and 11-hexadecynoic acids into (Z, Z)-11,13-hexadecadienoic and (Z)-13-hexadecen-11-ynoic acids, respectively, is initiated by abstraction of the hydrogen atom at the C13 position, followed by the fast elimination of the C14 hydrogen to give the double bond.
Description5 pages, 3 figures.-- PMID: 17253792 [PubMed].-- Supporting information (Additional methods and procedures, 63 pages) available at: http://pubs.acs.org/doi/suppl/10.1021/jo061592s/suppl_file/jo061592ssi20061124_060211.pdf
Publisher version (URL)http://dx.doi.org/10.1021/jo061592s
URIhttp://hdl.handle.net/10261/9502
DOI10.1021/jo061592s
ISSN1520-6904
Appears in Collections:(IQAC) Artículos

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