Syntheses of arsinolipids: non-isosteric analogues of phospholipids
โ Scribed by Nick L. Kordalis; Panayiotis V. Ioannou
- Publisher
- John Wiley and Sons
- Year
- 2000
- Tongue
- English
- Weight
- 77 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0268-2605
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โฆ Synopsis
Reaction of alkaline benzenearsonous and 2,3dihydroxypropylarsonous acids with rac-glycidol affords the corresponding arsinic acids, which after reduction with thiophenol are acylated with either fatty-acid chlorides/pyridine or fatty acids/dicyclohexylcarbodiimide/4dimethylaminopyridine and oxidized with hydrogen peroxide to give the arsinolipids (rac-2,3diacyloxypropyl)phenylarsinic and bis-(rac-2,3diacyloxypropyl)arsinic acids. The latter is a non-isosteric analogue of bisphosphatidic acid.
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Monoacylated glycosylglycerols are known anti-tumor promoters: in order to study the role of the ester function in the modulation of their activity, we synthesized several analogues in which the acyloxy moiety was substituted with isosteric chains linked to the glycosylglycerol skeleton through an e