- Synthesis and biological activity of anticancer ether lipids that are specifically released by phospholipase A2 in tumor tissue
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The clinical use of anticancer lipids is severely limited by their ability to cause lysis of red blood cells prohibiting intravenous injection. Novel delivery systems are therefore required in order to develop anticancer ether lipids (AELs) into clinicall
- Andresen, Thomas L.,Jensen, Simon S.,Madsen, Robert,J?rgensen, Kent
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p. 7305 - 7314
(2007/10/03)
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- New optically pure dimethylacetals of glyceraldehydes and their application for lipid and phospholipid synthesis
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A convenient synthesis of new and enantiometrically pure 2-O-protected D-glyceraldehyde dimethylacetals as chiral C-3 building blocks for the synthesis of lipids and phospholipids is described.Benzyl- or allylethers are used as protecting groups in position 2 and 5 of D-mannitol.These intermediates are converted to 2-O-benzyl- or 2-O-alkyl-D-glyceraldehyde dimethylacetals by cleavage with periodic acid in methanol.The two dimethylacetals are useful for the synthesis of mixed chain phospholipids with natural configuration of ester-ester, ester-ether or ether-ether composition.Also, triglycerides with three different alkyl chains, ester of ether, can be prepared.As an example of the varsatility of the new intermediates, we describe the synthesis of 1-O-hexadecyl-2-O-acetyl-sn-glycero-3-phosphocho;ine, the so-called 'platelet activating factor' (PAF), via 1-O-hexadecyl-2-O-benzyl-sn-glycerol. Keywords: Synthetic phospholipids; PAF; Phospholipid analogues; Synthesis; Chiral pool; Glyceraldehyde; C-3 building blocks; Optical purity
- Massing, Ulrich,Eibl, Hansjoerg
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p. 211 - 224
(2007/10/02)
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- Syntheses of a glycerophospholipid, C16-platelet activating factor and a palmitoyl analogue of M-5, an anti-inflammatory glyceroglycolipid
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From a chiral C4-epoxide (-)-3, which is one of the synthons in our synthetic strategy for complex lipids, a glycerophospholipid C16-platelet activating factor (C16-PAF, 1) and a palmitoyl analogue (2) of an anti-inflammatory glyceroglycolipid M-5, which was previously isolated from the Okinawan marine sponge Phyllospongia foliascens, have been synthesized.
- Shibuya,Kawashima,Narita,Kitagawa
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p. 1166 - 1169
(2007/10/02)
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- An Efficient Stereocontrolled Route to Both Enantiomers of Platelet Activating Factor and Analogues with Long-Chain Esters at C2: Saturated and Unsaturated Ether Glycerolipids by Opening of Glycidyl Arenesulfonates
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Both enantiomers of various ether/ester glycerophospholines (R)- and (S)-1, including platelet activating factor (PAF, 2), have been synthesized from arenesulfonate derivatives of glycidol ((R)- and (S)-3) that are readily available in high enantiomeric p
- Guivisdalsky, Pedro N.,Bittman, Robert
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p. 4643 - 4648
(2007/10/02)
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- NOVEL ENANTIOSELECTIVE SYNTHESIS OF PLATELET ACTIVATING FACTOR AND ITS ENANTIOMER VIA RING OPENING OF GLYCIDYL TOSYLATE WITH 1-HEXADECANOL
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(2R)-and(2S)-Glycidyl tosylates 3 and 3' were used to synthesize platelet activating factor 1 and its enantiomer 2 in very high optical purity via the ring-opened ether-linked glycerol tosylate 4 and 4'
- Guivisdalsky, Pedro N.,Bittman, Robert
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p. 4393 - 4396
(2007/10/02)
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