76738-49-3

Basic information

• Product Name: 5S,6R-6-epi-Leukotriene A₄ methyl ester
• Synonyms: 5S,6R-6-epi-Leukotriene A₄ methyl ester
• CAS NO: 76738-49-3
• Molecular Weight: 332.483
• Mol File: 76738-49-3.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 5S,6R-6-epi-Leukotriene A₄ methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5S,6R-6-epi-Leukotriene A₄ methyl ester(76738-49-3)
• EPA Substance Registry System: 5S,6R-6-epi-Leukotriene A₄ methyl ester(76738-49-3)

Safety Data

• Hazardous Substances Data: 76738-49-3(Hazardous Substances Data)

Upstream product

• 75817-52-6 -triphenyl-phosphonium-bromid 
• 73958-01-7 4-[3-((E)-3-Oxo-propenyl)-oxiranyl]-butyric acid methyl ester 
• 80629-41-0 methyl ester of 5(S)-hydroperoxy-6(E)-8,11,14(Z)-eicosatetranoic acid 
• 66688-21-9 (E)-methyl 7-oxo-hept-5-enoate 
• 73957-99-0 (+/-)-methyl trans-5,6-epoxy-7-hydroxyheptanoate 
• 73427-12-0 methyl 6-formyl-5,6-trans-epoxyhexanoate 
• 64244-45-7 methyl (Z)-7-hydroxy-5-heptenoate 
• 73957-95-6 C₃₂H₃₀O₁₀ 
• 73957-98-9 C₂₉H₃₀O₉S 
• 73958-09-5 Phosphorane of (Z)-3-nonen-1-yl-triphenylphosponium bromide 
• 73958-00-6 4-[(2S,3R)-3-((1Z,3E)-5-Oxo-penta-1,3-dienyl)-oxiranyl]-butyric acid methyl ester 
• 63753-78-6 C₃₀H₂₈O₉ 
• 73957-96-7 C₂₅H₂₆O₈ 
• 55797-81-4 C₂₆H₂₂O₈ 

Downstream Products

• 73466-14-5 (7E,9E,11Z,14Z)-(5S,6R)-6-[(R)-2-((S)-4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid 
• 79026-72-5 (5R,6S)-LTC₄ 
• 73836-78-9 (7E,9E,11Z,14Z)-6-[2-Amino-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid 
• 72025-60-6 LTC4 
• 73958-10-8 (7E,9E,11Z,14Z)-(5S,6R)-6-[2-(4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester 
• 91944-21-7 7Z,9E,11E,14Z-LTD₄ methyl ester 
• 73836-78-9 7Z,9E,11E,14Z-LTD₄ 
• 75443-89-9 7Z,9E,11E,14Z-LTE₄ 
• 89461-64-3 7Z,9E,11E,14Z-LTE₄ methyl ester 
• 72025-60-6 (7E,9E,11Z,14Z)-(5S,6R)-6-[2-(4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid 
• 72025-60-6 leukotriene C1 
• 72025-60-6 5(S)-hydroxy-6(R)-glutathionyl-7,9-E-11,14-Z-eicosatetraenoic acid 
• 72025-60-6 leukotriene C4 
• 72025-60-6 (7E,9Z,11Z,14Z)-(5S,6R)-6-[(S)-2-((S)-4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid 

Relevant articles and documents

Stereochemistry and Mechanism of the Biosynthesis of Leukotriene A4 from 5(S)-Hydroperoxy-6(E),8,11,14(Z)-eicosatetraenoic Acid. Evidence for an Organoiron Intermediate

The pathway of biosynthesis of leukotriene A4 (LTA4, 2) from 5(S)-hydroperoxy-6(E),8,11,14(Z)-eicosatetraenoic acid (5-S-HPETE, 1) has been explored by the comparative study of (S)- and (R)-lipoxygenase (LO) enzymes as catalysts.The purified LO from potato, an S-lipoxygenase, converts (anaerobically) 1 to 2 (determined as the characteristic hydrolysis mixture of two epimeric 5,6-diols and two epimeric 5,12-diols), as previously reported by Samuelsson et al.However, the 8-R-LO from the coral Plexaura homomalla transforms 1 (anaerobically) into 6-epi-LTA4 (6).Theobserved divergence of stereopathways agrees with predictions based on the intermediacy of organoiron intermediates in enzymic lipoxygenation (Scheme I) and detailed in Schemes II and III.Further evidence for the intervention of such intermediates has been obtained by trapping experiments under pure O2 at pressures of 1-60 atm.Under O2 pressure 1 is converted by the potato LO to a new product, the bis(hydroperoxide) 7, whereas the coral LO converts 1 to the diastereomeric bis(hydroperoxide) 9.

AN EFFICIENT AND SIMPLE METHOD THE CONVERSION OF 15-HPETE TO 14,15-EPETE (LIPOTRIENE A) AND 5-HPETE TO LEUKOTRIENE A AS THE METHYL ESTERS

Simple new methodology is described for the synthesis from arachidonic acid of the important eicosanoids lipotriene A methyl ester (5) and leukotriene A methyl ester (10), a key feature being the use of a novel chemical method for effecting the allylic hydroperoxide oxiranyl carbinol rearrangement.

CHEMICAL CONVERSION OF ARACHIDONIC ACID TO SLOW REACTING SUBSTANCES

The synthesis of slow reacting substances, leukotrienes C, D, and E, can be accomplished conveniently by a stereoselective biomimetic route.Details are provided for the conversion of 5-HPETE methyl ester 4 to leukotriene methyl ester (2) and thence to leukotrienes C and D.