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Eicosanoid


DATA No : XPR3301 INFORMANT : Shouzo Yamamoto

NAME : 5(S)-Hydroxy-6(R)-S-cysteinylglycinyleicosa-7(E),9(E),11(Z),14(Z)-tetraenoic acid

COMMON NAME: LEUKOTRIENE D4
SYMBOL: LTD4
FORMULA: C25H40O6N2S1 MOL.WT (average) : 496.661


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BIOLOGICAL ACTIVITY
Leukotriene D4 stimulates airway smooth muscles and causes bronchoconstriction. Vascular permeability is enhanced. Gasstrointestinal smooth muscles are contracted (Ref. 0021/0022). Leukotriene D4 binds to a receptor with 7 transmembrane domains coupled to Gia/o protein (CysLT1) with an affinity higher by two orders of magnitude than that of leukotriene C4 (Ref. 0030).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:METHANOL (Ref. 1026)
SPECTRAL DATA
UV SPECTRA:l MeOHmax = 270(e 32,000), 280(e 40,000), 290(e 31,000)nm (Ref. 1027)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:N-ACETYL, 5-TRIMETHYLSILYL ETHER DIMETHYL ESTER derivative ; 638(M+), 623, 607, 548, 508, 405, 404, 315, 314, 274, 273 (Ref. 1026)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Leukotriene D4 is produced by basophils, eosinophils and macrophages of various animal species upon various stimulations on the cells (Ref. 0021/0022).
CHEMICAL SYNTHESIS
(Ref. 1028)
[Table 0001]
METABOLISM
g-Glutamyl transpeptidase hydrolyzes the glutathione moiety of leukotriene C4 and produces leukotriene D4 liberating glutamic acid (Ref. 0022),
GENETIC INFORMATION
cDNA for CysLT1 was cloned (Ref. 0030).
NOTE

REFERENCES
[0021]
AUTHOR:Samuelsson, B., and Hammarstrom, S.
TITLE:Leukotrienes: a novel group of biologically active compounds PubMed ID:6293196
JOURNAL:Vitam Horm.
VOL:39 PAGE : 1-30 (1982)
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[0022]
AUTHOR:Hammarstrom, S.
TITLE:Leukotrienes PubMed ID:6311078
JOURNAL:Annu Rev Biochem.
VOL:52 PAGE : 355-377 (1983)
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[0030]
AUTHOR:Lynch, K. R., O'Neill, G. P., Liu, Q., Im, D. S., Sawyer, N., Metters, K. M., Coulombe, N., Abramovitz, M., Figueroa, D. J., Zeng, Z., et al.
TITLE:Characterization of the human cysteinyl leukotriene CysLT1 receptor PubMed ID:10391245
JOURNAL:Nature.
VOL:399 PAGE : 789-793 (1999)
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[1026]
AUTHOR:Morris, H. R., Taylor, G. W., Rokach, J., Girard, Y., Piper, P. J., Tippins, J. R., and Samhoun, M. N.
TITLE:Slow reacting substance of anaphylaxis, SRS-A; assignment of the stereochemistry PubMed ID:7422903
JOURNAL:Prostaglandins.
VOL:20 PAGE : 601-607 (1980)
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[1027]
AUTHOR:Lewis, R. A., Austen, K. F., Drazen, J. M., Clark, D. A., Marfat, A., and Corey, E. J.
TITLE:Slow reacting substances of anaphylaxis: identification of leukotrienes C-1 and D from human and rat sources PubMed ID:6106193
JOURNAL:Proc Natl Acad Sci U S A.
VOL:77 PAGE : 3710-3714 (1980)
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[1028]
AUTHOR:Cohen,N., Banner,B.L., Lopresti,R.J., Wong,F., Rosenberger,M., Liu,Y.-Y., Thom,E., and Liebman,A.A.
TITLE:Enantiospecific Syntheses of Leukotrienes C4, D4, and E4 and [14,153H2]Leukotriene E4 Dimethyl Ester.
JOURNAL:J. Am. Chem. Soc.
VOL:105 PAGE : 3661 -3672 (1983)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.