The conformational analysis of leukotriene D₄ in aqueous solution based on high-field nuclear magnetic resonance measurements

Abstract

. Can. J. Chem. 62, 1640 ( 1984). The conformational analysis of LTD, in D20 was carried out based on the analysis of vicinal proton-proton coupling constants, nonselective proton longitudinal relaxation times, and nuclear Overhauser effect data. The H6-C6 to C12 region of the molecule is transoid, the predominant rotamer about C5-C6 is gauche, and two rotamers can be used to describe the rotation about C12-C13. There are three rotamers that can be used to describe the rotation about the C21-C22 bond of cysteine. Finally, chelation between an ~b " , shift reagents and LTD, was not observed.MAKIKO SUGIURA, HELMUT BEIERBECK, GEORGE KOTOVYCH et PATRICE C. BELANGER. Can. J. Chem. 62, 1640 (1984). Faisant appel h une analyse des constantes de couplage proton-proton vicinales, des temps de relaxation longitudinaux non-selectifs des protons et de donnCes d'effet Overhauser nuclkaire, on a rCalisC une analyse conformationnelle du LTD, dans le D20. La region H6-C6 2 1 C12 de la molCcule est transoide, le rotamkre predominant autour de la liaison C5-C6 est gauche et deux rotameres peuvent &tre utilisCs pour decrire la rotation autour de la liaison C12-C13. On peut utiliser trois rotameres pour dtcrire la rotation autour de la liaison C21-C22 de la cystkine. Finalement, on n'a pas pu observe de chelation entre le Yb3', un reactif de contact, et le LTD,.[Traduit par le journal]

The conformations of prostacyclin and related prostaglandins

“…Not only is there good agreement between calculation and experiment, but alternative conformations could unambiguously be eliminated on the basis of nOe comparisons. Thus, as in the leukotriene series (29,30), quantitative nuclear Overhauser effects and, to a lesser extent, relaxation time measurements proved useful complements to vicinal coupling constants in the conformational analysis of complex molecules of biological interest.…”

The Detailed Conformational Study of a Leukotriene Antagonist, FPL-55712, using High-Field Nuclear Magnetic Resonance Spectroscopy

“…We have recently determined the conformations of leukotrienes B 4 and D 4 in aqueous solutions (5,6). These results can now be used in the design of analogs for these leukotrienes.…”

“…The normal 400 MHz NMR spectrum of FPL-55712 in CD 3 0D with a drop of C6 The results of the NOE experiments. The bottom trace is the normal, expanded spectrum ( 400 MHz) of the H14-H15-H16 region of FPL-55712, as perFigure 3.…”