10567-22-3Relevant articles and documents
Synthesis and Ruthenium-Catalyzed Enantioselective Hydrogenation of 3-O-Substituted 1,3-dihydroxypropan-2-ones
Cesarotti, Edoardo,Antognazza, Patrizia,Pallavicini, Marco,Villa, Luigi
, p. 2344 - 2349 (1993)
A number of 3-O-substituted 1,3-dihydroxypropan-2-ones have been synthesized in view of their potential use as prochiral precursors of optically active glycerols.Indeed, the oxo-ethers have been reduced to the corresponding 3-O-substituted glycerols via c
Activation of n-3 polyunsaturated fatty acids as oxime esters: A novel approach for their exclusive incorporation into the primary alcoholic positions of the glycerol moiety by lipase
Magnusson, Carlos D.,Haraldsson, Gudmundur G.
, p. 712 - 720 (2013/01/15)
A novel approach has been developed for activating the highly bioactive long-chain n-3 polyunsaturated fatty acids EPA and DHA as oxime esters and incorporating them exclusively to the end-positions of glycerol and enantiopure 1-O-alkylglycerols. The Candida antarctica lipase B was observed to display a superb regioselectivity when using the acetoxime esters of EPA and DHA as acyldonors under mild condition to keep acyl-migration side-reaction under complete control. Regiopure 1,3-diacylglycerols, 1-O-alkyl-3-acyl-sn-glycerols and their antipodes possessing EPA and DHA were afforded in very high purity and yields.
Autotaxin structure-activity relationships revealed through lysophosphatidylcholine analogs
North, E. Jeffrey,Osborne, Daniel A.,Bridson, Peter K.,Baker, Daniel L.,Parrill, Abby L.
experimental part, p. 3433 - 3442 (2009/09/30)
Autotaxin (ATX) catalyzes the hydrolysis of lysophosphatidylcholine (LPC) to form the bioactive lipid lysophosphatidic acid (LPA). LPA stimulates cell proliferation, cell survival, and cell migration and is involved in obesity, rheumatoid arthritis, neuropathic pain, atherosclerosis and various cancers, suggesting that ATX inhibitors have broad therapeutic potential. Product feedback inhibition of ATX by LPA has stimulated structure-activity studies focused on LPA analogs. However, LPA displays mixed mode inhibition, indicating that it can bind to both the enzyme and the enzyme-substrate complex. This suggests that LPA may not interact solely with the catalytic site. In this report we have prepared LPC analogs to help map out substrate structure-activity relationships. The structural variances include length and unsaturation of the fatty tail, choline and polar linker presence, acyl versus ether linkage of the hydrocarbon chain, and methylene and nitrogen replacement of the choline oxygen. All LPC analogs were assayed in competition with the synthetic substrate, FS-3, to show the preference ATX has for each alteration. Choline presence and methylene replacement of the choline oxygen were detrimental to ATX recognition. These findings provide insights into the structure of the enzyme in the vicinity of the catalytic site as well as suggesting that ATX produces rate enhancement, at least in part, by substrate destabilization.
D and L etherlipid stereoisomers and liposomes
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Page column 12, (2008/06/13)
A liposome having a lipid bilayer, where the lipid bilayer includes either the L or D stereoisomer of an ether lipid or a non-equal mixture of both. Most preferably the liposome also comprises (a) an underivatized phosphatidylcholine; (b) a sterol; (c) about 5-20 mole % of a phosphatidylethanolamine linked to a dicarboxylic acid at the ethanolamine group of the phosphatidylethanolamine, and (d) greater than about 10 mole % to less than about 30 mole % of either the L or D stereoisomer of an ether lipid. The liposome may be used as an anti-cancer or anti-inflammatory agent.
The chemical synthesis of a series of ether phospholipids from D-mannitol and their properties
Xia, Jie,Hui, Yong-Zheng
, p. 3131 - 3142 (2007/10/03)
The synthesis of the novel ether phospholipids from D-mannitol as homochiral material using a new method for the removal of a tert-butyldimethylsilyl group for hydroxyl protection without acyl migration and their properties including bioactivity are described.
Stereospecific and regiospecific ring opening of glycidol with primary and secondary alcohols mediated by diisobutylaluminium hydride
Erukulla, Ravi Kumar,Byun, Hoe-Sup,Locke, David C.,Bittman, Robert
, p. 2199 - 2200 (2007/10/02)
Regiospecific ring opening of (R)-(+)- or (S)-(-)-glycidol 1a, b with primary and secondary alcohols in the presence of diisobutylaluminium hydride provides 1-O-alkyl-sn-glycerol 2 without formation of the undesired regioisomer, 2-O-alkylglycerol 3.The configuration of the glycidol is preserved in the product.
Stereoselective Synthesis of Long-chain 1-O-(β-D-Maltosyl)-3-O-alkyl-sn-glycerols (Alkyl Glyceryl Ether Lysoglycolipids)
Prinz, Harald,Six, Lambert,Ruess, Klaus-Peter,Lieflaender, Manfred
, p. 217 - 225 (2007/10/02)
The synthesis of long-chain 2-O-benzyl-3-O-alkyl-sn-glycerols 5 was improved, making these compounds easily accessible for glycosylation experiments.Glycosylation with α-acetobromomaltose following a modified Koenings-Knorr procedure after removal of the protective groups yielded the title compound 9 in good yields.These compounds represent examples of alkyl glyceryl ether lysoglycolipids.Some properties of these amphiphilic compounds with a nonionic carbohydrate head-group differ not much (critical micell concentration, hemolytic activity), other properties differ very much (antitumor efficiency) from the properties of the analogous compounds with a zwitterionic phosphorylcholine head-group.
