79356-65-3Relevant academic research and scientific papers
SYNTHESIS, SEPARATION AND N.M.R. SPECTRA OF THREE DOUBLE BOND ISOMERS OF LEUKOTRIENE A METHYL ESTER
Baker, S. Richard,Jamieson, William B.,McKey, Stuart W.,Morgan, Sarah E.,Rackham, David M.,et al.
, p. 4123 - 4126 (1980)
The synthesis and h.p.l.c. separation of three double bond isomers of leukotriene A methyl ester is described, their stereochemistry being assigned by 1H N.M.R.
Stereochemistry and Mechanism of the Biosynthesis of Leukotriene A4 from 5(S)-Hydroperoxy-6(E),8,11,14(Z)-eicosatetraenoic Acid. Evidence for an Organoiron Intermediate
Corey, E. J.,Wright, Stephen W.,Matsuda, Seiichi P. T.
, p. 1452 - 1455 (2007/10/02)
The pathway of biosynthesis of leukotriene A4 (LTA4, 2) from 5(S)-hydroperoxy-6(E),8,11,14(Z)-eicosatetraenoic acid (5-S-HPETE, 1) has been explored by the comparative study of (S)- and (R)-lipoxygenase (LO) enzymes as catalysts.The purified LO from potato, an S-lipoxygenase, converts (anaerobically) 1 to 2 (determined as the characteristic hydrolysis mixture of two epimeric 5,6-diols and two epimeric 5,12-diols), as previously reported by Samuelsson et al.However, the 8-R-LO from the coral Plexaura homomalla transforms 1 (anaerobically) into 6-epi-LTA4 (6).Theobserved divergence of stereopathways agrees with predictions based on the intermediacy of organoiron intermediates in enzymic lipoxygenation (Scheme I) and detailed in Schemes II and III.Further evidence for the intervention of such intermediates has been obtained by trapping experiments under pure O2 at pressures of 1-60 atm.Under O2 pressure 1 is converted by the potato LO to a new product, the bis(hydroperoxide) 7, whereas the coral LO converts 1 to the diastereomeric bis(hydroperoxide) 9.
AN EFFICIENT AND SIMPLE METHOD THE CONVERSION OF 15-HPETE TO 14,15-EPETE (LIPOTRIENE A) AND 5-HPETE TO LEUKOTRIENE A AS THE METHYL ESTERS
Corey, E. J.,Su, Wei-guo,Mehrotra, Mukund M.
, p. 5123 - 5126 (2007/10/02)
Simple new methodology is described for the synthesis from arachidonic acid of the important eicosanoids lipotriene A methyl ester (5) and leukotriene A methyl ester (10), a key feature being the use of a novel chemical method for effecting the allylic hydroperoxide oxiranyl carbinol rearrangement.
CHEMICAL CONVERSION OF ARACHIDONIC ACID TO SLOW REACTING SUBSTANCES
Corey, E. J.,Barton, Alan E.
, p. 2351 - 2354 (2007/10/02)
The synthesis of slow reacting substances, leukotrienes C, D, and E, can be accomplished conveniently by a stereoselective biomimetic route.Details are provided for the conversion of 5-HPETE methyl ester 4 to leukotriene methyl ester (2) and thence to leukotrienes C and D.
A NOVEL STEREOSPECIFIC SYNTHESIS OF (+/-)-LEUKOTRIENE A4(LTA4),METHYL ESTER
Buck, Judith C.,Ellis, Frank,North, Peter, C.
, p. 4161 - 4162 (2007/10/02)
The reaction of the phosphonate 1 with the epoxyaldehyde 2 is reported as the key step in a novel stereospecific synthesis of (+/-)-LTA4, methyl ester 3.
CONVERGENT SYNTHESIS OF LEUKOTRIENE A METHYL ESTER
Gleason, John G.,Bryan, D. Boles,Kinzig, Charles M.
, p. 1129 - 1132 (2007/10/02)
A convergent total synthesis of methyl 5,6-oxido-6,9,11,14-eicosapentaenoate from oct-2-yn-1-ol and methyl 4-formylbutyrate is described.
Total synthesis of slow reacting substances (SRS). "Leukotriene C-2" (11-trans-leukotriene C) (3) and leukotriene D (4)
Corey,Clark, David A.,Marfat, Anthony,Goto, Giichi
, p. 3143 - 3146 (2007/10/02)
Syntheses are described for the "slow reacting substances" 11-trans-leukotriene C (3) (previously known as leukotriene C-2) and leukotriene D (4), the cys-gly analog of leukotriene C (2). The synthesized leukotrienes 3 and 4 were instrumental in the assignment of structure to these members of the family of naturally occuring slow reacting substances which includes also 2.
