- Enzymatic asymmetric hydroxylation of unnatural substrates with soybean lipoxygenase
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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.
- Yadav,Nanda,Rao
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- Total synthesis of 4-F3t-neuroprostane and its 4-epimer
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The first synthesis of 4-F3t-Neuroprostane 1a and its 4-epimer is described. This molecule presents an important contribution to the study of neuronal oxidative stress in DHA-ω3 depleted brain. The key step involves the introduction of two unsa
- Auvinet, Anne-Laure,Eignerová, Barbara,Guy, Alexandre,Kotora, Martin,Durand, Thierry
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- COMPOUNDS AND COMPOSITIONS FOR INTRACELLULAR DELIVERY OF AGENTS
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The disclosure features amino lipids and compositions involving the same. Nanoparticle compositions include an amino lipid as well as additional lipids such as phospholipids, structural lipids, PEG lipids, or a combination thereof. Nanoparticle compositions further including therapeutic and/or prophylactic agents such as RNA are useful in the delivery of therapeutic and/or prophylactic agents to mammalian cells or organs to, for example, regulate polypeptide, protein, or gene expression.
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- Asymmetric dihydroxylation and one-pot epoxidation routes to (+)- and (-)-posticlure: A novel trans-epoxide as a sex pheromone component of Orgyia postica (Walker)
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A highly enantioselective synthesis of (+)- and (-)-posticlure has been achieved. The synthesis features the Sharpless asymmetric dihydroxylation and one-pot epoxidation as the key steps.
- Fernandes, Rodney A,Kumar, Pradeep
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p. 6685 - 6690
(2007/10/03)
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- Soybean lipoxygenase and horseradish peroxidase catalysed asymmetric oxidation-reduction sequence for the synthesis of chiral (Z,E) diene-diols
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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.
- Yadav,Nanda,Bhaskar Rao
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p. 787 - 788
(2007/10/03)
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- Enantiospecific syntheses of leukotrienes C4, D4 and E4 and [14,15-3H2]leukotriene E4 dimethyl ester
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A 'chiral-pool' approach was employed to synthesize various leukotrienes (slow-reacting substance of anaphylaxis, SRS-A) enantiospecifically. The pivotal (S,S)-trans-epoxy alcohol 9 was prepared by efficient and facile routes starting from erythorbic acid (D-araboascorbic acid, 13). This epoxide could also be produced starting from D-glucose. The epimeric (S,R)-cis-epoxide 38 was obtained utilizing L-tartaric acid as the chiral starting material. Elaboration of 9 into leukotriene A4 methyl ester (5) and the potassium salts of leukotrienes C4 (4a), D4 (4b), and E4 (4c) was accomplished by standard methods. These salts exhibited potent contractile activities in the in vitro guinea pig ileum assay. Reduction of 14,15-dehydroleukotriene A4 methyl ester (44) with tritium gas gave [14,15-3H2]-5 and subsequently the dimethyl ester of [14,15-3H2]leukotriene E4 having a high specific activity of 40 Ci/mmol.
- Cohen,Banner,Lopresti,et al.
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p. 3661 - 3672
(2007/10/02)
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