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Título

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

Autor Abad, José Luis; Serra, Montserrat; Camps Díez, Francisco; Fabriàs, Gemma
Palabras clave Deuterated palmitic acids
Cryptoregiochemistry
Sex pheromone
Fecha de publicación 6-ene-2007
EditorAmerican Chemical Society
Citación The Journal of Organic Chemistry 72(3): 760-764 (2007)
ResumenThe 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.
Descripción 5 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
Versión del editorhttp://dx.doi.org/10.1021/jo061592s
URI http://hdl.handle.net/10261/9502
DOI10.1021/jo061592s
ISSN1520-6904
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