LBF20406LT01

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Upper classes: LB LBF



Leukotriene A4
LBF20406LT01.png
Structural Information
Systematic Name (5S,6S) -Epoxye- (trans-7,trans-9,cis-11,cis-14) -eicosatetraenoic acid
Common Name
  • Leukotriene A4
  • (5S,6S) -Epoxy- (7E,9E,11Z,14Z) -tetraenoic acid
  • 5 (S) ,6 (S) -Epoxyeicosa-7 (E) ,9 (E) ,11 (Z) ,14 (Z) -eicosatetraenoic acid
Symbol LTA4
Formula C20H30O3
Exact Mass 318.21949482599996
Average Mass 318.4504
SMILES C(CC=CCC=CC=CC=C[C@@H](O1)[C@@H]1CCCC(O)=O)CCC
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation [ α ]25
D
   =-21.9°(C=0.32,CYCLOHEXANE) Corey_EJ et al.
Refractive Index
Solubility SOL. IN CYCLOHEXANE,METHANOL Corey_EJ et al.. STABILITIES : to decompose to 5,12-DIHYDROXY-6,8,10,14-EICOSATETRAENOIC ACID and 5,6-DIHYDROXY-7,9,11,14-EICOSATETRAENOIC ACID under neutral aqueous solution at 37°C with one minite of half-life BorgeatPet al..
Source Leukotriene A4 is produced as an intermediate for the biosyntheses of leukotrienes B4 and C4 in polymorphonuclear leukocytes, mast cells and macrophages of various animal species Hammarstrom_S .
Chemical Synthesis Corey_EJ et al.
LBF20406LT01FT0001.gif
Metabolism Arachidonate 5-lipoxygenase is a bifunctional enzyme with a 5-oxygenase activity converting arachidonic acid to 5-hydroperoxy-6,8,11,14-eicosatetraenoic acid and a leukotriene A synthase activity converting the 5-hydroperoxy acid to leukotriene A4. The same enzyme produces leukotriene A4 from arachidonic acid via 5-hydroperoxy acid Ford-Hutchinson_AW et al.. The produced leukotriene A4 ia converted either to leukotriene B4 or to leukotriene C4 Hammarstrom_S .
Biological Activity Leukotriene A4 as such is biologically less active than its active metabolites, leukotrienes B4 and C4. For example, leukotriene A4 is at least two orders of magnitude less potent than leukotrienes C4, D4 and E4 in contraction of guinea pig lung strips Hammarstrom_S .
Genetic Information cDNA and genomic DNA for 5-lipoxygenase were cloned Funk_CD .
Note Stability:unstable in water around neutrality with a half life of about 1 min at 37°C and decomposes to 5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid and 5,6-dihydroxy-7,9,11,14-eicosatetraenoic acid Samuelsson_B et al.
Spectral Information
Mass Spectra METHYL ESTER ; 332(M+), 316, 300, 221, 189, 181, 129, 101 Mckay_SW et al.
UV Spectra METHYL ESTER ; λ MeOH
max
   = 269( ε 30,500), 278( ε 40,000), 287( ε 34,400) nm Corey_EJ et al.
IR Spectra
NMR Spectra
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406LT01 See above. Borgeat_P et al. 1979
n.a. LBF20406LT01 See above. Corey_EJ et al. 1979
n.a. LBF20406LT01 See above. Corey_EJ et al. 1980
n.a. LBF20406LT01 See above. Ford-Hutchinson_AW et al. 1994
n.a. LBF20406LT01 See above. Funk_CD 1993
n.a. LBF20406LT01 See above. Hammarstrom_S 1983
n.a. LBF20406LT01 See above. Mckay_SW et al. 1981
n.a. LBF20406LT01 See above. Samuelsson_B et al. 1982


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