Contents

Leukotriene A₄

Leukotriene A₄

Names
Preferred IUPAC name 4-{(2S,3S)-3-[(1E,3E,5Z,8Z)-Tetradeca-1,3,5,8-tetraen-1-yl]oxiran-2-yl}butanoic acid
Identifiers
CAS Number	72059-45-1 Y
3D model (JSmol)	Interactive image
Abbreviations	LTA4
ChEBI	CHEBI:15651 N
ChemSpider	4444074 N
IUPHAR/BPS	5214
KEGG	C00909 N
MeSH	D017572
PubChem CID	5280383
UNII	7Y7MPZ6563 Y
CompTox Dashboard (EPA)	DTXSID40903945
InChI InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-13,15,18-19H,2-5,8,14,16-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11+,15-13+/t18-,19-/m0/s1 N Key: UFPQIRYSPUYQHK-WAQVJNLQSA-N N InChI=1/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-13,15,18-19H,2-5,8,14,16-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11+,15-13+/t18-,19-/m0/s1 Key: UFPQIRYSPUYQHK-WAQVJNLQBZ
SMILES CCCCC/C=C\C/C=C\C=C\C=C\[C@H]1[C@@H](O1)CCCC(=O)O
Properties
Chemical formula	C20H30O3
Molar mass	318.457 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Chemical compound

Leukotriene A₄ (LTA₄) is a leukotriene, and is the precursor for the productions of leukotriene B₄ (LTB₄) and leukotriene C₄ (LTC₄).

Biosynthesis[edit]

Following the biosynthesis of eicosanoid, triggered as a result of infection or inflammation, the resulting arachidonic acid substrate is released from the cell membrane phospholipid will enter the lipooxygenase pathway to produce leukotriene A₄.^[1][2] In this pathway, arachidonic acid is converted into 5-hydroperoxyeicosatetraenoic acid (5-HPETE) as a result of a catalytic complex consisting of the enzyme 5-lipoxygenase (5-LO) and 5-lipoxygenase-activating protein (FLAP) in the presence of ATP and calcium ions.^[1][2][3] The resulting 5-HPETE yields the unstable allylic epoxide substrate LTA₄^[4] which is quickly hydrolyzed by the leukotriene A4 hydrolase (LTA₄H) enzyme to produce LTB₄, or synthesized by leukotriene C4 synthase (LTC₄S) with the addition of glutathione to produce LTC₄ which can be further metabolized to produce leukotriene D₄ (LTD₄) and leukotriene E₄ (LTE₄).^[5][4] The lipooxygenase pathway is one of several possible pathways including the cyclooxygenase pathway (also PGH synthase pathway), isoprostane pathway, and cytochrome P450 epoxygenases pathway following the arachidonic acid metabolism,^[6] but is the only pathway in which the subsequent steps will lead to the production of leukotrienes.

References[edit]