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 ^M^e^O^H_m_a_x = 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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