69494-16-2Relevant academic research and scientific papers
The synthesis of a 5-HETE photoaffinity ligand
Saha,Khanapure,Powell,Rokach
, p. 6313 - 6317 (2007/10/03)
The design and synthesis of a photoaffinity ligand 26, targeted at the 5h-dh, was accomplished. The synthesis was effected by two new synthetic routes which focus on the ω-hydroxy 5-HETE derivative 12 as a pivotal synthon. Preliminary results show ligand 26 to be an excellent substrate for the 5h-dh. (C) 2000 Elsevier Science Ltd.
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.
