- Improved synthesis of (E)-12-nitrooctadec-12-enoic acid, a potent PPARγ activator. development of a "buffer-Free" enzymatic method for hydrolysis of methyl esters
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Endogenous nitro-fatty acids, acting as partial agonist of PPARγ, are able to lower the insulin and glucose levels without the side effects associated with common antidiabetic drugs. (E)-12-Nitrooctadec-12-enoic acid, a potent activator of this peroxisome receptor, was synthesized in a very efficient sequence via a Henry-retro-Claisen ring fragmentation, followed by a novel enzymatic cleavage of methyl esters. The latter method was then applied in the last step of the synthesis of a few labile natural products, such as prostaglandins, isoprostanes, and phytoprostanes.
- Zanoni, Giuseppe,Valli, Matteo,Bendjeddou, Lyamin,Porta, Alessio,Bruno, Paolo,Vidari, Giovanni
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- Total synthesis of E1 and E2 isoprostanes by diastereoselective protonation
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A short total synthesis of the E-type isoprostanes has been achieved using a two-component coupling process combined with a diastereoselective protonation under reagent control. Mild cleavage of the silyl protective groups with cat. BiBr3 or HF/Py followed by enzymatic hydrolysis of the methyl ester afforded the free E-type isoprostanes.
- Rodríguez, Ana R.,Spur, Bernd W.
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p. 9249 - 9253
(2007/10/03)
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- Preparation of ent-prostaglandin E2
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The enantiomeric prostaglandins, exemplified by ent-PGE2, are apparently produced in vivo by the nonenzymatic oxidation of arachidonic acid. To assess the physiological activity of ent-PGE2, it was necessary to prepare it by total sy
- Taber, Douglass F,Jiang, Qin
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p. 5991 - 5994
(2007/10/03)
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- Racemic prostaglandins of the 2-series and analogs thereof
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This invention is racemic PGE 2, racemic PGF 2 α, racemic PGF 2 β, racemic PGA 2, racemic PGB 2, analogs of those, and processes for making them. These compounds are useful for a variety of pharmacological purposes, including anti-ulcer, inhibition of platelet aggregation, increase of nasal patency, abortion, and wound healing.
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- Enzymatic preparation and purification of prostaglandin E2.
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An enzymatic system has been developed for the production of prostaglandin E(2) (PGE(2)) from arachidonic acid by extracts of sheep seminal vesicular glands. The presence of glutathione insures high yields. A new procedure for the purification of PGE(2) was also developed, based on the dialysis of the biosynthesized product at pH 8 and extraction of the dialysate at pH 3 with chloroform. This procedure routinely gives yields of PGE(2) of 25-37% (from arachidonic acid) with a purity of 90-100%. Additional analytical proof of the identity of PGE(2) was provided by physicochemical characteristics of the crystalline thiosemicarbazide derivative, which can be readily prepared under mild conditions.
- Lapidus,Grant,Alburn
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p. 371 - 373
(2007/10/16)
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