Oxidized leukotrienes: Synthesis of 20-OH and 20-COOH LTD4. Possible metabolites in the lipoxygenase pathway
✍ Scribed by Julian Adams; Suzanne Milette; Joshua Rokach; Robert Zamboni
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- French
- Weight
- 209 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Leukotriene LTD4 analogs 20-OH LTD4 16 and ZO-COOH LTD4 17 were synthesized. These ti-oxidative derivatives are possible metã601ites of the natural product. The leukotrienes LTC4, LTD4 and LTE4, also known as SRS-A (slow reacting substance of anaphalaxis) are al1 potent spasmogens, producing smooth muscle contractions in mammalian organisms. Typically, doses as low as 0.3 ng/mL produce observable contractions of the guinea pig i1eum.l These compounds are produced from arachidonic acid via the 5-lipoxygenase cascade. Arachidonic acid is oxidized to give 5-hydroperoxy eicosatetraenoic acid (HPETE) and this compound is dehydrated stereospecifically producing the 5,6 expoxide, LTA4. which upon nucleophilic opening with the thiopeptide glutathione gives rise to LTC4. Specific enzymatic degradation of the peptide affords LTD4 and LTE4. The leukotrienes are believed to be important mediators in allergic reactions and are known to be formed during asthmatic states, inducing broncho-constriction. nur laboratories are primarily concerned with the biochemical and physiological roles of the leukotrienes and their metabolites.