392333-41-4

Upstream product

• 105-13-5 4-Methoxybenzyl alcohol 
• 6149-41-3 methyl ester (3-hydroxy) propionic acid 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 2746-25-0 p-Methoxybenzyl bromide 
• 135362-69-5 3-(4-methoxybenzyl)oxypropan-1-ol 

Downstream Products

• 1598413-56-9 (4S,6R)-7-(tert-butyldiphenylsilyloxy)-6-methylhept-1-en-4-yl 3-(4-methoxybenzyloxy) propanoate 
• 1414941-29-9 C₁₅H₂₁NO₆ 
• 1414941-30-2 C₁₅H₁₉NO₅ 
• 1414941-20-0 (S)-1-(2-(2-(4-methoxybenzyloxy)ethyl)oxazol-4-yl)but-3-en-1-ol 
• 1414941-31-3 methyl 2-(2-(4-methoxybenzyloxy)ethyl)oxazole-4-carboxylate 
• 1414941-19-7 methyl 2-(2-(4-methoxybenzyloxy)ethyl)oxazole-4-carboxylate 
• 392333-42-5 3-(4-Methoxy-benzyloxy)-propionic acid (5Z,8Z)-tetradeca-5,8-dienyl ester 

Relevant academic research and scientific papers

Total Synthesis of DHA and DPA n-3Non-Enzymatic Oxylipins

Oxylipins are formed in vivo from polyunsaturated fatty acids (PUFAs). A large structural variety of compounds is grouped under the term oxylipins, which differ from their formation mechanism (involving enzymes or not), as well as their chemical structures (cyclopentane, tetrahydrofuran, hydroxylated-PUFA, etc.). All structures of oxylipins are of great biological interest. Directly correlated to oxidative stress phenomenon, non-enzymatic oxylipins are used as systemic and/or specific biomarkers in various pathologies, and more especially, they were found to have their own biological properties. Produced in vivo as a non-separable mixture of isomers, their total synthesis is a keystone to answer biological questions. In this work, the total synthesis of three non-enzymatic oxylipins derived from docosahexaenoic acid (DHA) and docosapentanoic acid (DPAn-3) is described using a unique and convergent synthetic strategy.

Soybean lipoxygenase and horseradish peroxidase catalysed asymmetric oxidation-reduction sequence for the synthesis of chiral (Z,E) diene-diols

Unnatural synthetic substrates with a properly spaced prosthetic modifier having non-ionic hydroxy terminus undergoes soybean lipoxygenase catalysed asymmetric peroxidation followed by horseradish peroxidase induced reduction affords (Z, E)-dienediol in high enantiomeric excess.

Enzymatic asymmetric hydroxylation of unnatural substrates with soybean lipoxygenase

Surrogate substrates mimicking the natural substrate (linoleic acid) bearing a spacing prosthetic group with a non-ionic hydroxyl terminus undergo asymmetric hydroxylation with soybean lipoxygenase. The prosthetic modifier supplies the missing structural features needed for enzymatic recognition and controls the regiochemical outcome of the reaction by its high hydrophobic content. The effect of pH on the regiochemistry clearly shows that all the substrates can arrange themselves at the active site of soybean lipoxygenase in only one orientation leading to formation of hydroperoxides by oxygenation at the ω-6 carbon.