83058-42-8Relevant academic research and scientific papers
Facile preparation of leukotrienes C4, D4 and E 4 containing carbon-13 and nitrogen-15 for quantification of cysteinyl leukotrienes by mass spectrometry
Ghomashchi, Farideh,Bollinger, James G.,Gelb, Michael H.
, p. 729 - 733 (2007)
With the recent ability to use combined liquid chromatography/electrospray tandem mass spectrometry to analyze for several eicosanoids in biological samples in a single and rapid experiment, heavy isotope-labeled eicosanoids are needed as internal standards in order to quantify eicosanoid analytes. The present study describes a practical preparation of cysteinyl leukotrienes (leukotriene C4, D4 and E4) with three 13C atoms and one 15N atom in the cysteinyl residue. The method involves solid-phase peptide synthesis to make glutathione with heavy isotopes in the cysteinyl residue and reaction of this tripeptide with commercially available leukotriene A4 methyl ester to give labeled leukotriene C4 methyl ester, which is hydrolyzed to labeled leukotriene C4. Labeled leukotriene E4 is prepared in the same way with the use of labeled cysteine. Labeled leukotriene D4 is prepared by treatment of labeled leukotriene C4 with commercially available γ-glutamyl transpeptidase. Copyright
Catalytic asymmetric synthesis of Leukotriene B4
Yang, Pengfei,Zhong, Jiangchun,Ji, Kaijie,Yin, Jingwei,Li, Shuoning,Wei, Siyuan,Zhou, Yun,Wang, Lifeng,Wang, Min,Bian, Qinghua
, p. 1596 - 1601 (2017/10/20)
Leukotriene B4 1 was prepared from two chiral synthons 8 and 14. The chiral secondary alcohols of 8 and 14 were constructed by BINOL/Ti(OiPr)4 catalyzed enantioselective alkynylzinc addition to aldehydes.
An efficient total synthesis of leukotriene B4
Primdahl, Karoline Gangestad,Tungen, Jorn Eivind,Aursnes, Marius,Hansen, Trond Vidar,Vik, Anders
supporting information, p. 5412 - 5417 (2015/05/20)
Lipid mediators have attracted great interest from scientists within the chemical, medicinal, and pharmaceutical research community. One such example is leukotriene B4 which has been the subject of many pharmacological studies. Herein, we report a convergent and stereoselective synthesis of this potent lipid mediator in 5% yield over 10 steps in the longest linear sequence from commercial starting materials. The key steps were a stereocontrolled acetate-aldol reaction with Nagao's chiral auxiliary and a Z-selective Boland reduction. All spectroscopic data were in agreement with those previously reported.
A short stereocontrolled synthesis of leukotriene B4
Chemin, Denis,Linstrumelle, Gerard
, p. 1943 - 1952 (2007/10/12)
A short convergent total synthesis of LTB4 1 is accomplished by an efficient palladium-catalyzed coupling reaction of two easily accessible chiral synthons 3 and 4.
Total synthesis of (+)-leukotriene B4 methyl ester and its 5-epimer from (R)-glycidol
Avignon-Tropis,Treilhou,Pougny,Frechard-Ortuno,Linstrumelle
, p. 7279 - 7286 (2007/10/02)
The Pd-Cu coupling reaction of a chiral hydroxy-(E,E)-iododiene with a racemic acetylenic alcohol followed by reduction of the dienyne leads to the desired (Z,E,E) geometry and allows synthesis of LTB4 and its 5-epimer after separation of diast
Synthesis of 12-O-benzoyl 6,7,14,15-tetrahydro leucotriene B4 methyl ester, a precursor of labelled LTB4.
Pontikis, R,Musci, A,Merrer, Y le,Depezay, JC
, p. 968 - 975 (2007/10/02)
Leucotriene B4 (LTB4), a 5-lipoxygenase metabolite of arachidonic acid, is an important mediator of inflammatory processes and of acute hypersensitivity reactions.The availability of isotopically labelled versions of this natural metabolite is of primary
An efficient synthesis of leukotriene B4
Avignon-Tropis,Treilhou,Lebreton,Pougny,Frechard-Ortuno,Huynh,Linstrumelle
, p. 6335 - 6336 (2007/10/02)
Leukotriene B4 (5S, 12R) and its epimer (5R, 12R) have been prepared by coupling a chiral hydroxy vinyl borane with a racemic vinyl iodide, followed by the easy separation of the thus formed diastereomers.
