Eicosanoid

DATA No : XPR6001 INFORMANT : Shouzo Yamamoto

NAME : 5(S)-Hydroperoxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid

COMMON NAME	:
SYMBOL	:	5(S)-HPETE
FORMULA	:	C₂₀H₃₂O₄ MOL.WT (average) : 336.466

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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:

DENSITY	:

SOLUBILITY	:	DIETHYL ETHER (Ref. 1077). ETHYL ACETATE (Ref. 1078)

SPECTRAL DATA

UV SPECTRA	:	l ^M^e^O^H_m_a_x = 230nm (Ref. 1076)

IR SPECTRA	:

NMR SPECTRA	:

MASS SPECTRA	:

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM

Arachidonic acid is oxygenated at the position 5 by the 5-oxygenase activity of arachidonate 5-lipoxygenase, and transformed to 5(S)-hydroperoxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid, which is further converted to leukotriene A4 by the same enzyme. Thus, the 5-hydroperoxy acid is an intermediate for leukotriene A4 synthesis (Ref. 0025).

GENETIC INFORMATION

cDNA and genomic DNA of 5-lipoxygenase were cloned (Ref. 0007).

NOTE

REFERENCES

[0007]

AUTHOR	:	Funk, C.D.
TITLE	:	Molecular biology in the eicosanoid field . PubMed ID:8341804
JOURNAL	:	Progr. Nucleic Acid Res.
VOL	:	45 PAGE : 67 -98 (1993)

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[0025]

AUTHOR	:	Ford-Hutchinson, A. W., Gresser, M., and Young, R. N.
TITLE	:	5-Lipoxygenase PubMed ID:7979243
JOURNAL	:	Annu Rev Biochem.
VOL	:	63 PAGE : 383-417 (1994)

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[1076]

AUTHOR	:	Corey,E.J., Wright,S.W. and Matsuda,S.P.T.
TITLE	:	Stereochemistry and Mechanism of the Biosynthesis of Leukotriene A4 from 5(S)-Hydroxy-6(E),8,11,14(Z)-eicosatetraenoic Acid. Evidence for an Organoiron Intermediates.
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	111 PAGE : 1452 -1455 (1989)

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[1077]

AUTHOR	:	Porter,N.A., Logan,J. and Kontoyiannidou,V.
TITLE	:	Preparation and Purification of Arachidonic Acid Hydroperoxides of Biological Importance.
JOURNAL	:	J. Org. Chem.
VOL	:	44 PAGE : 3177 -3181 (1979)

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[1078]

AUTHOR	:	Boeynaems, J. M., Brash, A. R., Oates, J. A., and Hubbard, W. C.
TITLE	:	Preparation and assay of monohydroxy-eicosatetraenoic acids PubMed ID:7004263
JOURNAL	:	Anal Biochem.
VOL	:	104 PAGE : 259-267 (1980)

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