Synthesis of arsinolipids. II. A non-isosteric analogue of fully acylated cardiolipin.
2-Hydroxypropane-1,3-bis(arsonic acid) after six successive reactions gives the arsinolipid 2-acyloxy-As, As'-bis[2,3-di(acyloxy)propyl]propane-1,3-diylbis(arsinic acid) in 20-40% overall yields. This arsinolipid is a non-isosteric analogue of the fully acylated cardiolipin. The R- and S-glycidol, used to create the backbone of the lipid, give the optically active RR and SS, respectively, arsinolipids, while the rac-glycidol produces a mixture of diastereomers (a racemic pair, RR and SS, and two meso forms with an RS configuration). Some properties of these arsinolipids are described, from which the most interesting are the facile hydrolysis of the middle acyl group and their tendency to absorb environmental water.
Ioannou
Panayiotis V
PV
Department of Chemistry, University of Patras, Patras, Greece. ioannou@chemistry.upatras.gr
D000215:Acylation; D001152:Arsenicals / Q000737:chemistry*; D002308:Cardiolipins / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D006868:Hydrolysis; D008055:Lipids / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D014867:Water / Q000737:chemistry
D001152:Arsenicals; D002308:Cardiolipins; D008055:Lipids; D014867:Water; C006633:arsine