64031-52-3Relevant academic research and scientific papers
Studies related to fatty acid desaturation, III: Preparation and use of thiaoleic acids
Poulain,Noiret,Nugier-Chauvin,Patin
, p. 35 - 40 (1997)
New thiaoleic acid methyl esters 1 have been prepared as models for studies on Δ12-saturation, Convergent synthetic pathways to those acids from the 10-(tetrahydropyranyloxy)-dec-1-yne 2 are described. After saponification, their inhibitory effect on the in vivo desaturation of [1-14C] oleic acid into [1-14C] linoleic acid has been evaluated using green algae, Chlorella sorokiniana, as a biological model. This result may indicate that the oleyl-desaturase initiates dehydrogenation of a normal substrate by hydrogen atom abstraction at C-13. VCH Verlagsgesellschaft mbH, 1997.
A chemoenzymatic approach to hydroperoxyeicosatetraenoic acids. Total synthesis of 5(S)-HPETE
Dussault,Lee
, p. 218 - 226 (2007/10/02)
A new synthetic approach to enantiomerically pure hydroperoxyeicosatetraenoic acids (HPETEs) is described in which the tetraene skeleton is assembled through chemoselective olefination of a protected hydroperoxy aldehyde. Soybean lipoxygenase-mediated dioxygenation of both natural and unnatural fats produces hydroperoxy dienes in high enantiomeric excess; the observed regioselectivity supports a revised hypothesis for substrate specificity. Protection of the diene hydroperoxides as peroxy ketals is followed by regioselective ozonolysis to afford enantiomerically pure 4-peroxy 2,3-enals which undergo olefination to produce peroxytetraenoates. Removal of the monoperoxy ketal and the methyl ester affords enantiomerically pure HPETEs. The generality of the strategy is illustrated with the first chemical synthesis of 5(S)-HPETE.
