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Synthesis of Stereoisomeric Phospholipids for Use in Membrane Studies

  • Chapter
Methods in Membrane Biology

Abstract

Twenty-five years ago, the first successful synthesis of a 3-sn-phosphatidylcholine was reported by Baer and Kates (1950). This accomplishment not only established conclusively the constitution and configuration of a naturally occurring phospholipid as being “L-α-,” or, in the newer nomenclature, “3-sn-,” but made a phospholipid available for the first time in pure form for biochemical and biophysical studies. The procedure used involved phosphorylation of a 1,2-diacyl-sn-glycerol with monophenylphosphoryl dichloride, followed by esterification with choline chloride and removal of the phenyl group by catalytic hydrogenolysis (Fig. 1). Variations of this procedure have since been used by Baer and his coworkers to synthesize all the major classes of phosphoglycerides (e.g., phosphatidylethanolamines, phosphatidylserines, phosphatidylglycerols, etc.), as well as minor and unusual phosphoglycerides, including ether and/or phosphono analogues (see reviews by Baer, 1963, 1965).

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References

  • Abdulla, Y. H., and Davison, A. N., 1965, Succinyl phosphatides as intermediates in the succinate-dehydrogenation reaction of yeast, Biochem. J. 96:1OC.

    Google Scholar 

  • Allen, C. F., Good, P., Davies, H. F., and Fowler, S. C., 1964, Plant and chloroplast lipids. I. Separation and composition of major spinach lipids, Biochem. Biophys. Res. Commun. 15: 424.

    PubMed  CAS  Google Scholar 

  • Anse11, G. B., and Spanner,. S., 1965, Action of phospholipase C on ethanolamine plasmalogen(2-acyl-1-alkenyl-glycero-phosphorylethanolamine), Biochem. J. 97: 375.

    PubMed  CAS  Google Scholar 

  • Aneja, R., and Chadha, J. S., 1971a, Acyl-chlorodeoxy-glycerophosphorylcholines: Structure of the so-called cyclic lysolecithins, Biochim. Biophys. Acta 239: 84.

    PubMed  CAS  Google Scholar 

  • Aneja, R., and Chadha, J. S., 1971b, A total synthesis of phosphatidylcholines, Biochim. Biophys. Acta 248: 455.

    CAS  Google Scholar 

  • Aneja, R., and Davies, A. P., 1974, Nucleophilic substitution in glycerol derivatives. Part V. Formation of 1,3-diacylglycerol-2-phosphates in the reaction of 1,2-diacyl-3- iododeoxy-rac-glycerol with silver dibenzyl phosphate, Chem. Phys. Lipids 12: 39.

    CAS  Google Scholar 

  • Aneja, R., Chadha, J. S., Cubero Robles, E., and Van Daal, R., 1969a, Partial synthesis of phosphatidylethanolamines, Biochim. Biophys. Acta 187: 439.

    CAS  Google Scholar 

  • Aneja, R., Chadha, J. S., and Knaggs, J. A., 19696, The use of N-tritylation in the partial synthesis of 1,2-diacyl-sn-glycerophosphorylethanolaminés, Biochim. Biophys. Acta 187: 579.

    Google Scholar 

  • Aneja, R., Chadha, J. S., Davies, A. P., and Rose, C. A., 1969c, The condensation of aziridine with phosphatidic acid; synthesis of 1,2-diacyl-sn-glycero-3-phosphorylethanolamine, Chem. Phys. Lipids 3: 286.

    PubMed  CAS  Google Scholar 

  • Aneja, R., Chadha, J. S., and Davies, A. P., 1970, A general synthesis of glycerophospholipids, Biochim. Biophys. Acta 218: 102.

    PubMed  CAS  Google Scholar 

  • Arnold, D., Weltzien, H. U., and Westphal, O., 1967, Synthesis of choline phosphatides. 3. Synthesis of lysolecithins and their ether analogues, Ann. Chem. 709: 234.

    CAS  Google Scholar 

  • Baer, E., 1951, Synthesis of enantiomeric a-phosphatidic acids, J. Biol. Chem. 189: 235.

    PubMed  CAS  Google Scholar 

  • Baer, E., 1952a, L-a-Glycerophosphoric acid (barium salt), Biochem. Prep. 2: 31.

    CAS  Google Scholar 

  • Baer, E., 1952b, Synthesis of enantiomeric a-biphosphatidic acids, J. Biol. Chem. 198: 152.

    Google Scholar 

  • Baer, E., 1963, The synthesis of phospholipids, Progr. Chem. Fats Lipids 6: 33.

    Google Scholar 

  • Baer, E., 1965, From the trioses to the synthesis of natural phospholipids: A research trail of forty years, J. Am. Oil Chem. Soc. 42: 257.

    PubMed  CAS  Google Scholar 

  • Baer, E., 1974, Phosphonolipids 26. Mixed-acid phosphonocephalins. Synthesis of a’- stearoyl-ß-oleoyl-L-a-glyceryl(2-aminoethyl)phosphonate, Can. J. Biochem. 52: 57.

    Google Scholar 

  • Baer, E., and Basu, H., 1969, Phosphonic acid analogues of carbohydrate metabolites. 1.Synthesis of L- and D- dihydroxypropylphosphonic acid, Can. J. Biochem. 47: 955.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Basu, H., 1970, Synthesis of phosphotidic acids, Can. J. Biochem. 48: 1010.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Basu, H., 1972, Phosphonolipids. 25. Synthesis of a’-octadecyl-ß-hexadeca-noyl-L-a-glyceryl(2-aminoethyl)phosphonate, a homologue of a naturally occurring alpha-monoether-phosphonocephalin, Can. J. Biochem. 50: 988.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Blackwell, J., 1963, Phosphatidyl-L-2-amino-l-propanols. I. Synthesis of dimyristoyl and distearoyl L-a-glycerophosphoryl-L-2-amino-l-propanol, J. Biol. Chem. 238: 3591.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Blackwell, J., 1964, Synthesis of a-cephalins by a new procedure. II. Dioleoyl and dilinoleoyl L-a-cephalins, Biochemistry 3: 975.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Buchnea, 1958a, Synthesis of unsaturated a,ß-diglycerides. I. D-a,ß-diolein and L-α,β-diolein, J. Bilo. Chem. 230: 447

    CAS  Google Scholar 

  • Baer, E., and ISU(:I111Cfi, D., 19.,ßu, Synthesis of unsaturated and L-a,ß-diolein, J. Biol. Chem. 230: 447.

    Google Scholar 

  • Baer, E., and Buchnea, D., 19586, Synthesis of unsaturated a-phosphatidic acids and abisphosphatidic acids. Cardiolipin substitutes. IV., Arch. Biochem. Biophys. 78: 294.

    Google Scholar 

  • Baer, E., and Buchnea, D., 1959, Synthesis of saturated and unsaturated L-a-lecithins; acylation of the cadmium chloride compound of L-a-glycerophosphorylcholine, Can. J. Biochem. Physiol. 37: 953.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Eckstein, F., 1962, Phosphatidyl threonines. I. Synthesis of distearoyl-L-aglycerophosphoryl-L-threonine, J. Biol. Chem. 237: 1449.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Fischer, H. O. L., 1945, Synthesis of a homologous series of optically active normal aliphatic a-monoglycerides (L-series), J. Am. Chem. Soc. 67: 2031.

    CAS  Google Scholar 

  • Baer, E., and Fischer, H. O. L., 1948, L-(+)-propylene glycol, J. Am. Chem. Soc. 70: 609

    PubMed  CAS  Google Scholar 

  • Baer, E., and Kates, M., 1948, L-a-glycerophosphorylcholine, J. Am. Chem. Soc. 70: 1394.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Kates, M., 1950, Synthesis of enantiomeric a-lecithins, J. Am. Chem. Soc. 72: 942.

    CAS  Google Scholar 

  • Baer, E., and Kindler, A., 1962, L-a-(dioleoyl)lecithin. An alternate route to its synthesis, Biochemistry 1: 518.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Martin, F., 1951, Synthesis of n-a-lecithin, an active antigen component in the serodiagnosis of syphilis, J. Biol. Chem. 193: 835.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Maurukas, J., 1952, An improved procedure for the synthesis of enantiomeric a-lecithins, J. Am. Chem. Soc. 74: 158.

    CAS  Google Scholar 

  • Baer, E., and Maurukas, J., 1955, Phosphatidyl serine, J. Biol. Chem. 212: 39.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Pal, B. C., 1967a, Phosphatidyl-a-methylcholine, Can. J. Biochem. 45: 309.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Pal, B. C., 1967b, Phosphonolipids. 13. Synthesis of dihydroceramideaminoethylphosphonates, Can. J. Biochem. 45: 1478.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Pavanaram, S. K., 1961a, N-Methyl cephalins. Synthesis of distearoyl-L-a glycerophosphoryl-N-methyl-ethanolamine, J. Biol. Chem. 236: 1269.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Pavanaram, S. K., 1961b, N,N-Dimethyl cephalins. Synthesis of distearoyl-La-glycerophosphoryl-N,N-dimethyl-ethanolamine, J. Biol. Chem. 236: 2410.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Rao, G. V., 1963, Phosphatidyl 2-amino-2-methylpropanols. I. Synthesis of dimyristoyl and distearoyl L-a-glycerophosphoryl-2-amino-2-methylpropanol, J. Biol. Chem. 238: 1941.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Rao, K. V. J., 1967, Phosphonolipids. 8. Synthesis of phosphonic acid analogues of diether L-a-lecithins, Can. J. Biochem. 45: 317.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Sarma, G. R., 1969, Total synthesis of a naturally occurring ceramide aminoethylphosphonate and its enantiomer, Can. J. Biochem. 47: 603.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Stancer, H. C., 1953, The synthesis of L-a-glycerophosphoryl ethanolamine and some comments on the stereochemical aspects of the biosynthesis of glycerolphosphatides from carbohydrates, J. Am. Chem. Soc. 75: 4510.

    CAS  Google Scholar 

  • Baer, E., and Stanacev, N. Z., 1964, Phosphonolipids. 1. Synthesis of phosphonic acid analogues of cephalin, J. Biol. Chem. 239: 3209.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Stanacev, N. Z., 1965a, Phosphonolipids. 2. Synthesis of dialkyl-L-a-glyceryl(2-aminoethyl) phosphonates, J. Biol. Chem. 240: 44.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Stanacev, N. Z., 1965b, Phosphonolipids. 5. Synthesis of phosphonate analogues of L-a-lecithins, J. Biol. Chem. 240: 3754.

    PubMed  CAS  Google Scholar 

  • Baer, E., and Zschocke, A., 1961, Phosphatidyl hydroxyprolines. I. Synthesis of distearoyl L-a-glycerophosphoryl-LG, Ls-hydroxyproline, J. Biol. Chem. 236: 1273.

    PubMed  CAS  Google Scholar 

  • Baer, E., Buchnea, D., and Newcombe, A. G., 1956, Synthesis of unsaturated a-lecithins. I. L-a-(dioleoyl)-lecithin, J. Am. Chem. Soc. 78: 232.

    CAS  Google Scholar 

  • Baer, E., Suzuki, Y., and Blackwell, J., 1963, Synthesis of a-cephalins by a new procedure. Biochemistry 2: 1227.

    PubMed  CAS  Google Scholar 

  • Ballou, C. E., and Pizer, L. I., 1960, Synthesis of an optically active myo-inositol-1-phosphate, J. Am. Chem. Soc. 82: 3333.

    CAS  Google Scholar 

  • Barry, P. J., and Craig, B. M., 1955, Glyceride synthesis. I. Synthesis of symmetrical diglycerides from dihydroxyacetone and allyl alcohol, Can. J. Chem. 33: 716.

    CAS  Google Scholar 

  • Barzilay, I., and Lapidot, Y., 1971, The use of o-nitrophenyl-sulfenyl group as amino protecting group in the synthesis of phosphatidylethanolamine, Chem. Phys. Lipids 7: 93.

    CAS  Google Scholar 

  • Barzilay, I., and Lapidot, Y., 1969, The modified synthesis of phosphatidylethanolamine, Chem. Phys. Lipids 3: 280.

    PubMed  CAS  Google Scholar 

  • Baumann, W. J., and Mangold, H. K., 1966a, Reaction of aliphatic methanesulfonates. 2. Synthesis of long-chain di-and trialkylglycerylethers, Error! Hyperlink reference not valid .. Chem. 31: 498.

    CAS  Google Scholar 

  • Baumann, W. J., and Mangold, H. K., 1966b, Alkoxy lipids. I. Preparation and characterization of alkoxy-diglycerides and dialkoxy-glycerides, Biochim. Biophys. Acta 116: 570.

    PubMed  CAS  Google Scholar 

  • Baumann, W. J., Schmidt, H. H. O., Kramer, J. K. G., and Mangold, H. K., 1968, Alk-1- enyl ethers of glycerol and ethanediol, Z. Physiol. Chem. 349: 1677.

    CAS  Google Scholar 

  • Berecoechea, J., Faure, M., and Anatol, J., 1968, Phospholipid ethers. Synthesis of 1,2dipalmityl-3-phosphoric acid and bis-(1,2-dipalmitylglyceryl-3)-pyrophosphoric acid, Bull. Soc. Chim. Biol. 50: 1561.

    PubMed  CAS  Google Scholar 

  • Bieber, L. L., Cheldelin, V. J., and Newburgh, R. W., 1963, Studies on ß-methylcholinecontaining phospholipids derived from carnitine, J. Biol. Chem. 238: 1262.

    PubMed  CAS  Google Scholar 

  • Bird, P. R., and Chadha, J. S., 1966, Synthesis of diacyl-L-l-glycerol bromohydrins (intermediates in synthesis of phosphatidic acids), Tetrahedron Lett. 1966: 4541.

    Google Scholar 

  • Bird, P. R., De Haas, G. H., Heemskerk, C. H. T., and van Deenen, L. L. M., 1965, Synthetic lecithins containing one short-chain fatty acid and their breakdown by phospholipase A, Biochim. Biophys. Acta 98: 566.

    PubMed  CAS  Google Scholar 

  • Body, D. R., and Gray, G. M., 1967a, The isolation and characterization of phosphatidylglycerol and a structural isomer from pig lung, Chem. Phys. Lipids 1: 254.

    CAS  Google Scholar 

  • Body, D. R., and Gray, G. M., 19676, Semi-lyso-bisphosphatidic acid: An unusual phospholipid isolated from rabbit lung, Chem. Phys. Lipids 1: 424.

    Google Scholar 

  • Bonsen, P. P. M., and de Haas, G. H., 1967, Silver di-t-butyl phosphate, a useful reagent in the synthesis of phospholipids. Synthesis of mixed-acid phosphatidic acid and phosphatidylglycerophosphate, Chem. Phys. Lipids 1: 100.

    CAS  Google Scholar 

  • Bonsen, P. P. M., de Haas, G. H., and van Deenen, L. L. M., 1966, The synthesis of 3phosphatidyl-1’-glycerol, Chem. Phys. Lipids 1: 33.

    CAS  Google Scholar 

  • Bonsen, P. P. M., Burbach-Westerhuis, G. J., de Haas, G. H., and van Deenen, L. L. M., 1972, Chemical synthesis of lecithin analogues as potential inhibitors of phospholipase A, Chem. Phys. Lipids 8: 199.

    PubMed  CAS  Google Scholar 

  • Brockerhoff, H., and Yurkowski, M., 1965, Simplified preparation of L-a-glycerophosphorylcholine, Can. J. Biochem. 43: 1777.

    PubMed  CAS  Google Scholar 

  • Brotherus, J., and Renkonen, O., 1974, Isolation and characterization of bis-phosphatidic acid and its partially deacylated derivatives from cultured BHK cells, Chem. Phys. Lipids 13: 11.

    PubMed  CAS  Google Scholar 

  • Brotherus, J., Renkonen, O., Herrmann, J., and Fischer, W., 1974, Novel stereoconfiguration in lyso-bis-phosphatidic acid of cultured BHK cells, Chem. Phys. Lipids 13: 178.

    PubMed  CAS  Google Scholar 

  • Buchnea, P 1971, of mixed-acid (C,a) diacvl-sn-glycerol enantiomers, Lipids 6: 734.

    Google Scholar 

  • Buchnea, D., 1974, Detritylation by silicic acid—boric acid column chromatography, Lipids 9: 55.

    CAS  Google Scholar 

  • Bushnev, A. S., Zvonkova, E. N., and Evstigneeva, R. P., 1975, A synthetic approach to ceramidephosphorylethanolamines, Chem. Phys. Lipids 14: 263.

    CAS  Google Scholar 

  • Chacko, G. K., and Hanahan, D. J., 1968, Chemical synthesis of 1–0-(D)- and 3-O(L)-glyceryl monoethers, diethers, and derivatives: Glycerides, monoester phospholipids, and diether phospholipids, Biochim. Biophys. Acta 164: 252.

    PubMed  CAS  Google Scholar 

  • Chacko, G. K., and Hanahan, D. J., 1969, Chemical synthesis of phosphonic acid mono-ether analogues of phosphatidylethanolamine and phosphatidyl choline, Biochim. Biophys. Acta 176: 190.

    PubMed  CAS  Google Scholar 

  • Chadha, J. S., 1968, Synthesis of L-a-phosphatidylethanolamines from diacyl-L-a-glycerolbromohydrins, Chem. Phys. Lipids 2: 415.

    CAS  Google Scholar 

  • Chadha, J. S., 1970, Preparation of crystalline L-a-glycerophosphorylcholine—cadmium chloride adduct from commercial egg lecithin, Chem. Phys. Lipids 4: 104.

    CAS  Google Scholar 

  • Chen, J. S., and Barton, P. G., 1970, Studies of dialkyl ether phospholipids. 1. Chemical synthesis of some model compounds, Can. J. Biochem. 48: 585.

    PubMed  CAS  Google Scholar 

  • Colacicco, G., and Rapport, M. M., 1967, A simplified preparation of phosphatidylinositol, J. Lipid. Res. 8: 513.

    PubMed  CAS  Google Scholar 

  • Coulon-Morelec, M. J., and Giraud, D., 1965, Preparation semisynthétique de l’acide pyrophosphatidique et du phosphatidylglycérol à partir d’acides phosphatidiques naturels, Bull. Soc. Chim. Biol. 47: 47.

    PubMed  CAS  Google Scholar 

  • Cubero Robles, E., and Roels, G. F. M., 1971, Preparation of deacylated phosphoglycerides, Chem. Phys. Lipids 6: 31.

    CAS  Google Scholar 

  • Cubero Robles, E., and van den Berg, D., 1969, Synthesis of lecithins by acylation of sn-glycero-3-phosphorylcholine with fatty acid anhydrides, Biochim. Biophys. Acta 187: 520.

    PubMed  CAS  Google Scholar 

  • Daemen, F. J. M., 1967, A convenient synthesis of phosphatidylethanolamines, Chem. Phys. Lipids 1: 476.

    CAS  Google Scholar 

  • Daemen, F. J. M., de Haas,G. H., and van Deenen, L. L. M., 1963, An improved synthesis of a mixed-acid L-a-phosphatidylethanolamine containing a polyunsaturated fatty acid, Rec. Tray. Chim. 82: 487.

    CAS  Google Scholar 

  • Damico, R., Callahan, R. C., and Mattson, F. H., 1967, Synthesis of glycerol 1,3-dihexadecyl ether, J. Lipid Res. 8: 63.

    PubMed  CAS  Google Scholar 

  • de Haas, G. H., and van Deenen, L. L. M., 1960, Partial synthesis of “mixed-acid” L-alecithins, Tetrahedron Lett. 1960: 7.

    Google Scholar 

  • de Haas, G. H., and van Deenen, L. L. M., 1961, Synthesis of enantiomeric mixed-acid phosphatides, Rec. Tray. Chim. 80: 951.

    Google Scholar 

  • de Haas, G. H., and van Deenen, L. L. M., 1963a, Stereospecific action of phospholipase A on ß-lecithins, Biochim. Biophys. Acta 70: 469.

    CAS  Google Scholar 

  • de Haas, G. H., and van Deenen, L. L. M., 1963, Synthesis of bis-phosphatidic acids, unpublished data.

    Google Scholar 

  • de Haas, G. H., and van Deenen, L. L. M., 1963c, Cardiolipin and derivatives. I. Synthesis of an acyl derivative of diphosphatidylglycerol, Rec. Tray. Chim. 82: 1163.

    Google Scholar 

  • de Haas, G. H., and van Deenen, L. L. M., 1964, The site of action of phospholipase A on fi-lecithin, Biochim. Biophys. Acta 84: 469.

    Google Scholar 

  • de Haas, G. H., and van Deenen, L. L. M., 1965a, Structural identification of isomeric lysolecithins, Biochim. Biophys. Acta 106: 315.

    PubMed  Google Scholar 

  • de Haas, G. H., and van Deenen, L. L. M., 1965, Cardiolipin and derivatives. II. Synthesis of diphosphatidylglycerol, Rec. Tray. Chim. 84: 436.

    Google Scholar 

  • de Haas, G. H., Daemen, F. J. M., and van Deenen, L. L. M., 1962, The site of action of phosphatide acyl-hydrolase (phospholipase A) on mixed phosphatides containing a polyunsaturated acid, Biochim. Biophys. Acta 65: 260.

    Google Scholar 

  • de Haas, G. H., van Zutphen, H., Bonsen, P. P. M., and van Deenen, L. L. M., 1964, Synthesis of mixed-acid phosphatidylserine containing unsaturated fatty acids, Rec. Tray. Chim. 83: 99.

    Google Scholar 

  • de Haas, G. H., Bonsen, P. P. M., and van Deenen, L. L. M., 1966, Studies on cardiolipin. III. Structural identity of ox-heart cardiolipin and synthetic diphosphatidylglycerol, Biochim. Biophys. Acta 116: 114.

    PubMed  Google Scholar 

  • de Haas, G. H., Bonsen, P. P. M., Pieterson, W. A., and Van Deenen, L. L. M., 1971, Studies on phospholipase A and its zymogen from porcine pancreas. III. Action of the enzyme on short-chain lecithins, Biochim. Biophys. Acta 239: 252.

    PubMed  Google Scholar 

  • Demel, R. A., Geurts van Kessel, W. S. M., and van Deenen, L. L. M., 1972, The properties of polyunsaturated lecithins in monolayers and liposomes and the interactions of these lecithins with cholesterol, Biochim. Biophys. Acta 266: 26.

    CAS  Google Scholar 

  • Dousset, N., Quan, D. Q., and Douste-Blazy, L., 1973, Synthese d’une 1-acy1–2-glutarylsn-glycero-3-phosphorylcholine, Chem. Phys. Lipids 11: 73.

    CAS  Google Scholar 

  • Eibl, H., and Lands, W. E. M., 1970, Phosphorylation of 1-alkenyl-2-acyl-glycerols and preparation of 2-acyl-phosphoglycerides, Biochemistry 9: 423.

    PubMed  CAS  Google Scholar 

  • Eibl, H., Arnold, D., Weltzien, H. U., and Westphal, O., 1967, Zur Synthese von alpha-und beta-Lecithinen und Ihren Atheranalogen, Liebig’s Ann. Chem. 709: 226.

    CAS  Google Scholar 

  • Faure, M., and Troestler, J., 1967, Méthodes de préparations des acides phosphatidiques. II. Obtention de l’acide phosphatidic par dégradation enzymatique de la lécithine par la phospholipase C, Bull. Soc. Chim. Biol. 49: 279.

    CAS  Google Scholar 

  • Fedorova, G. N., Serebrennikova, G. A., Yefimova, A. G., and Yevstigneeva, R. P., 1971, Synthesis of cis,cis-1-O-(octadecadien-l,9-y1)-sn-glycerol, Sh. Org. Khim. 7: 957.

    CAS  Google Scholar 

  • Ghosh, D., and Tinoco, J., 1972, Monolayer interactions of individual lecithins with natural sterols, Biochim. Biophys. Acta 266: 41.

    PubMed  CAS  Google Scholar 

  • Ghosh, D., Lyman, R. L., and Tinoco, J., 1971, Behavior of specific natural lecithins and cholesterol at air—water interface, Chem. Phys. Lipids 7: 173.

    PubMed  CAS  Google Scholar 

  • Gigg, J., and Gigg, R., 1967a, Preparation of unsymmetrical diglycerides, J. Chem. Soc. 1967: 431.

    Google Scholar 

  • Gigg, J., and Gigg, R., 19676, 1-O-Benzyl-L-glycerol and D-(glycerol-1,2-carbonate), J. Chem. Soc. 1967: 1865.

    Google Scholar 

  • Gigg, J., and Gigg, R., 1968a, A synthesis of 1-O-octadec-cis-l’-enyl-L-glycerol, J. Chem. Soc. 1968: 16.

    Google Scholar 

  • Gigg, J., and Gigg, R., 1968b, Synthesis of neutral plasmalogen, J. Chem. Soc. 1968: 2030.

    Google Scholar 

  • Gordon, D. T., and Jensen, R. G., 1972, Synthesis of 1,2-dilinoleoyl-and 1,2-dipalmitoylsn-3-glycerophosphorylcholine, Lipids 7: 261.

    CAS  Google Scholar 

  • Gupta, S. C., and Kummerow, F. A., 1959, Improved procedures for preparing glycerol ethers, Error! Hyperlink reference not valid .. Chem. 24: 409.

    CAS  Google Scholar 

  • Haest, C. W. M., de Gier, J., Op den Kamp, J. A. F., Bartels, P., and van Deenen, L. L. M., 1972, Changes in permeability of S. aureus and derived liposomes with varying lipid composition, Biochim. Biophys. Acta 255: 720.

    PubMed  CAS  Google Scholar 

  • Hanahan, D. J., and Brockerhoff, H., 1960, A synthetic route to mixed-acid L-a-lecithins and D-a,ß-diglycerides, Arch. Biochem. Biophys. 91: 326.

    PubMed  CAS  Google Scholar 

  • Hanahan, D. J., Ekholm, J., and Jackson, C. M., 1963, Structure of glyceryl ethers and the glyceryl-ether phospholipids of bovine erythrocytes, Biochemistry 2: 630.

    PubMed  CAS  Google Scholar 

  • Hancock, A. J., and Kates, M., 1973, Structure determination of the phosphatidylglycerosulfate (diether analogue) from Halobacterium cutirubrum, J. Lipid Res. 14: 422.

    CAS  Google Scholar 

  • Haverkate, F., and van Deenen, L. L. M., 1964, The stereochemical configuration of phosphatidylglycerol, Biochim. Biophys. Acta 84: 106.

    PubMed  CAS  Google Scholar 

  • Haverkate, F., and van Deenen, L. L. M., 1965, Isolation and chemical characterization of phosphatidyl glycerol from spinach leaves, Biochim. Biophys. Acta 106: 78.

    PubMed  CAS  Google Scholar 

  • Hessel, L. W., Morton, I. D., Todd, A. R., and Verkade, P. E., 1954, Phosphatidic acids and derivatives. IV. Synthesis of a-glycerophosphatidic acids from glycerol-a-iodohydrin, Rec. Tray. Chim. 73: 150.

    CAS  Google Scholar 

  • Hintze, U., and Gercken, G., 1975, Synthesis and properties of phosphatidyl carnitine and phosphatidyl fi-methyl choline, Lipids 10: 20.

    PubMed  CAS  Google Scholar 

  • Hirt, R., and Berchtold, R., 1957, Zur Synthese der Phosphatide. 1. Eine neue Synthese der Phosphatidylethanolamine, Hely. Chim. Acta 40: 1928.

    CAS  Google Scholar 

  • Hirt, R., and Berchtold, R., 1958, Zur Synthese der Phosphatide. 2. Eine neue Synthese der Lecithine, Pharm. Acta Hely. 33: 349.

    CAS  Google Scholar 

  • Howe, R. J., and Malkin, T., 1951, X-ray and thermal examination of the glycerides. XI. 1,2-Diglycerides and observations on 1,3-diglycerides, J. Chem. Soc. 1951: 2663.

    Google Scholar 

  • Jensen, R. G., 1972, Synthesis of enantiomeric diacylglycerols, in: Topics in Lipid Chemistry ( F. D. Gunstone, ed.), Vol. 3, pp. 1–35, Logos Press, London.

    Google Scholar 

  • Jensen, R. G., and Gordon, D. T., 1972, Synthesis of phosphoglycerides, Lipids 7: 611.

    CAS  Google Scholar 

  • Johnson, M. E., Simon, S., Kauffman, J. W., and MacDonald, R. C., 1973, A synthetic lecithin-containing branched-chain fatty acid: Physical properties and membrane studies, Biochim. Biophys. Acta 29: 587.

    Google Scholar 

  • Joo, C. N., and Kates, M., 1969, Synthesis of enantiomeric forms of 2,3-di-O-phytanyglycerol and 2,3-di-O-phytanylglycerophosphates, Biochim. Biophys. Acta 176: 278.

    PubMed  CAS  Google Scholar 

  • Joo, C. N., Shier, T., and Kates, M., 1968, Characterization and synthesis of mono-and diphytanyl ethers of glycerol, J. Lipid Res. 9: 782.

    PubMed  CAS  Google Scholar 

  • Kates, M., 1955, Hydrolysis of lecithin by plant plastid enzymes, Can. J. Biochem. Physiol 33: 575.

    PubMed  CAS  Google Scholar 

  • Kates, M.,. 1972, Chemistry and metabolism of ether-linked lipids in extremely halophilic bacteria, in: The Ether Bond in Lipids ( F. Snyder, ed.), pp. 351–398, Academic Press, New York.

    Google Scholar 

  • Kates, M., and Hancock, A. J., 1976, Synthesis of monophytanyl ether analogues of lysophosphatidic acid and lysophosphatidylglycerol, Chem. Phys. Lipids 17.

    Google Scholar 

  • Kates, M., and Sastry, P. S., 1969, Phospholipase D, Methods in Enzymol. 14: 197.

    CAS  Google Scholar 

  • Kates, M., Chan, T. H., and Stanacev, N. Z., 1963, Aliphatic diether analogues of glyceride-derived lipids. I. Synthesis of D-a,ß-dialkyl glycerol ethers, Biochemistry 2: 394.

    CAS  Google Scholar 

  • Kates, M., Palameta, B., and Yengoyan, L. S., 1965, Aliphatic diether analogues of glyceride-derived lipids. II. Synthesis of naturally occurring L-2,3-di-O-3’,7’,11’,15’tetramethylhexadecyl glycerol, Biochemistry 4: 1595.

    PubMed  CAS  Google Scholar 

  • Kates, M., Park, C. E., and Palameta, B., 1971, Synthesis of diphytanyl ether analogues of phosphatidic acid and cytidine diphosphate diglyceride, Can. J. Biochem. 49: 437.

    Google Scholar 

  • Kates, M., Chen, J. S., and Joo, C. N., 1976a, Synthesis of dialkyl ether analogues of phosphatidylglycerol, Chem. Phys. Lipids in press.

    Google Scholar 

  • Kates, M., Hancock, A. J., and Joo, C. N., 1976b, Synthesis of 1-O-phytanyl dihydroxyacetone phosphate, Chem. Phys. Lipids in press.

    Google Scholar 

  • Klopfenstein, W. E., de Kruyff, B., Verkleij, A. J., Demel, R. A., and Van Deenen, L. L. M., 1974, Differential scanning calorimetry on mixtures of lecithin, lysolecithin, and cholesterol, Chem. Phys. Lipids 13: 215.

    CAS  Google Scholar 

  • Klyashchitskii, B. A., Shvets, V. I., and Preobrazhenskii, N. A., 1969, On the nomenclature of asymmetrically substituted myoinositol derivatives with particular reference to phosphatidylinositols, Chem. Phys. Lipids 3: 393.

    PubMed  CAS  Google Scholar 

  • Komaratat, P., and Kates, M., 1975, The lipid composition of a halotolerant species of Staphylococcus epidermidis, Biochim. Biophys. Acta 398: 464.

    Google Scholar 

  • Lands, W. E. M., and Zschocke,,k., 1965, A new synthesis of L-1-O-benzyl glycerol, J. Lipid Res. 6: 324.

    PubMed  CAS  Google Scholar 

  • Lapidot, Y., Barzilay, I., and Hajdu, J., 1969, Synthesis of diacyl-DL- (and -L)-a-glycerol phosphate, Chem. Phys. Lipids 3: 125.

    PubMed  CAS  Google Scholar 

  • LeCocq, J., and Ballou, C. E., 1964, On the structure of cardiolipin, Biochemistry 3:976. Long, C., Odavic, R., and Sargent, E. J., 1967, The chemical nature of the products obtained by action of cabbage-leaf phospholipase D on lysolecithin: The structure of lysolecithin, Biochem. J. 102: 221.

    Google Scholar 

  • MacDougall, J. C., and Phizackerley, P. J. R., 1969, Isomers of glucosaminylphosphatidylglycerol in Bacillus megaterium, Biochem. J. 114: 361.

    CAS  Google Scholar 

  • Malkin, T., and Bevan, T. H., 1957a, Synthesis of glycerides, Prog. Chem. Fats Lipids 4:63. Malkin, T., and Bevan, T. H., 1957b, Synthesis of phospholipids, Prog. Chem. Fats Lipids 4: 97.

    Google Scholar 

  • Marinetti, G. V., 1964, Hydrolysis of cardiolipin by snake venom phospholipase A, Biochim. Biophys. Acta 84: 55.

    PubMed  CAS  Google Scholar 

  • Mattson, F. H., and Volpenheim, R. A., 1962, Synthesis and properties of glycerides, J. Lipid Res. 3: 281.

    CAS  Google Scholar 

  • Molotkovsky, J. G., and Bergelson, L. D., 1973, Synthesis of an unsaturated mixed-acid phosphatidylinositol of natural configuration. A new procedure for resolving racemic alcohols, Chem. Phys. Lipids 11: 135.

    Google Scholar 

  • Newman, M. S., and Renoll, M., 1945, Improved preparation of isopropylidene glycerol, J. Am. Chem. Soc. 67: 1621.

    CAS  Google Scholar 

  • Newman, M. S., and Renoll, M., 1955, Isopropylidene glycerol, Org. Synth. 3: 502.

    Google Scholar 

  • Oswald, E. O., Piantadosi, C., Anderson, C. E., and Snyder, F., 1966, The synthesis of 14C- and 3H-labeled glycerol ethers, Lipids 1: 241.

    PubMed  CAS  Google Scholar 

  • Palameta, B., and Kates, M., 1966, Aliphatic diether analogues of glyceride-derived lipids. 3. Synthesis of dialkenyl and mixed alkyl-alkenyl glycerol ethers, Biochemistry 5: 618.

    PubMed  CAS  Google Scholar 

  • Paltauf, F., 1969, The intestinal absorption of 1,2- and 1,3-dialkyl glycerol ethers and of diether phospholipids, Biochim. Biophys. Acta 176: 818.

    PubMed  CAS  Google Scholar 

  • Paltauf, F., 1972, Intestinal uptake and metabolism of alkyl acyl glycerophospholipids and of alkyl glycerophospholipids in the rat, Biochim. Biophys. Acta 260: 352.

    PubMed  CAS  Google Scholar 

  • Paltauf, F., 1973, Synthesis of alkoxylipids, Chem. Phys. Lipids 11: 270.

    CAS  Google Scholar 

  • Paltauf, F., and Holasek, A., 1973, Enzymatic synthesis of plasmalogens. Characterization of the 1-O-alkyl-2-acyl-sn-glycero-3-phosphorylethanolamine desaturase from mucosa of hamster small intestine, J. Biol. Chem. 248: 1609.

    PubMed  CAS  Google Scholar 

  • Paltauf, F., and Spener, F., 1968, An improved synthesis of 1,2-dialkyl glycerol ethers and the synthesis of 14C labeled trialkyl glycerol ethers, Chem. Phys. Lipids 2: 168.

    PubMed  CAS  Google Scholar 

  • Paltauf, F., Hauser, H., and Phillips, M. C., 1971, Monolayer characteristics of some 1,2diacyl.1-alkyl-2-acyl. and 1,2-dialkyl phospholipids at the water—air interface, Bicchim. Biophys. Acta 249: 539.

    Google Scholar 

  • Pfeiffer, F. R., Miao, C. K., and Weisbach, J. A., 1970, Glycerolipids. 3. Stereospecific synthesis of D-1,2-diglycerides and L-1,2-diglycerides via glycerol carbonates, Error! Hyperlink reference not valid .. Chem. 35: 221.

    CAS  Google Scholar 

  • Piantadosi, C., Ishaq, K. S., Wykle, R. L., and Snyder, F., 1971, Synthesis and characterization of 1-O-alkydihydroxy-acetone phosphate and derivatives, Biochemistry 10: 1417.

    PubMed  CAS  Google Scholar 

  • Porck, A. J. E., and Craig, B. M., 1955, Glyceride synthesis. II. Preparation of symmetrical saturated monoacid diglycerides from 2-O-benzylglycerol, Can. J. Chem. 33: 1286.

    CAS  Google Scholar 

  • Pugh, E., and Kates, M., 1975, A simplified procedure for synthesis of di-[14C]acyl lecithins, J. Lipid Res. 16: 392.

    PubMed  CAS  Google Scholar 

  • Rabinson, Y., Diver-Haber, A., Kanfer, J. M., and Shapiro, D., 1968, Synthetic studies on Sphingolipids. XIII. ß-Bromoethylphosphorylceramides as key intermediates in the synthesis of sphingomyelin and its ethanolamine analogues, Chem. Phys. Lipids 2: 223.

    Google Scholar 

  • Rakhit, S., Bagli, J. F., and Deghenghi, R., 1969, Phospholipids. Part I. Synthesis of phosphatidylethanolamines, Can. J. Chem. 47: 2906.

    CAS  Google Scholar 

  • Redwood, W. R., Pfeiffer, F. R., Weisbach, J. A., and Thompson, T. E., 1971, Physical properties of bilayer membranes formed from a synthetic saturated phospholipid in n-decane, Biochim. Biophys. Acta 233: 1.

    PubMed  CAS  Google Scholar 

  • Reman, F. C., Demel, R. A., de Gier, J., van Deenen, L. L. M., Eibl, H., and Westphal, O., 1969, Studies on the lysis of red cells and bimolecular lipid leaflets by synthetic lysolecithins, lecithins, and structural analogues, Chem. Phys. Lipids 3: 221.

    PubMed  CAS  Google Scholar 

  • Rosenthal, A. F., 1966, New partially hydrolyzable synthetic analogues of lecithin, phossphatidylethanolamine, and phosphatidic acid, J. Lipid Res. 7: 779.

    PubMed  CAS  Google Scholar 

  • Rosenthal, A. F., 1975, Chemical synthesis of phospholipids and analogues of phospholipids containing carbon—phosphorus bonds, Methods in Enzymol. 35: 429.

    CAS  Google Scholar 

  • Rosenthal, A. F., and Pousada, M., 1965, Phosphonate analogues of cephalin, Rec. Tray. Chim. 84: 833.

    CAS  Google Scholar 

  • Rosenthal, A. F., and Pousada, M., 1969, Two synthetic phosphonate analogues of lecithin, Lipids 4: 37.

    PubMed  CAS  Google Scholar 

  • Rosenthal, A. F., Kosolapoff, G. M., and Geyer, R. P., 1964, Nonhydrolyzable synthetic analogs of phosphatidic acids, Rec. Tray. Chim. 83: 1273.

    CAS  Google Scholar 

  • Rosenthal, A. F., Chodsky, S. V., and Han, S. C., 1969, Diether phosphinate lecithin: Chemical synthesis and effects on phospholipase C, Biochim. Biophys. Acta 187: 385.

    PubMed  CAS  Google Scholar 

  • Rosenthal, A. F., Vargas, L., and Han, S. C., 1972, Synthesis of optically active dietherphosphinate analogues of lecithin, Biochim. Biophys. Acta 260: 369.

    PubMed  CAS  Google Scholar 

  • Saunders, R. M., and Schwarz, H. P., 1966, Synthesis of phosphatidylglycerol and diphosphatidylglycerol, J. Am. Chem. Soc. 88: 3844.

    PubMed  CAS  Google Scholar 

  • Selinger, Z., and Lapidot, Y., 1966, Synthesis of fatty acid anhydrides by reaction with dicyclohexylcarbodiimide, J. Lipid Res. 7: 174.

    PubMed  CAS  Google Scholar 

  • Serebrennikova, G. A., Chebyshev, A. V., Vtorov, I. B., Fedorova, G. N., and Evstigneeva, R. P., 1971, Synthesis of phosphatidalethanolamine, cephalin plasmalogen, Khim. Prir. Soedin. 7:825 (C. A. 76: 99045 ).

    Google Scholar 

  • Serebrennikova, G. A., Chebyschev, A. V., Vtorov, I. B., Fedorova, G. N., and Evstigneeva, R. P., 1972, Synthesis of phosphatidalethanolamine (cephalin-plasmalogen), Error! Hyperlink reference not valid .. Kh. 8: 1171.

    CAS  Google Scholar 

  • Shapiro, D., 1965, Chemical synthesis of sphingolipids, J. Am. Oil Chem. Soc. 42: 267.

    PubMed  CAS  Google Scholar 

  • Shapiro, D., 1969, Chemistry of Sphingolipids, Hermann, Paris.

    Google Scholar 

  • Shapiro, D., and Flowers, H. M., 1959, The synthesis of dihydrocerebroside, J. Am. Chem. Soc. 81: 2023.

    CAS  Google Scholar 

  • Shapiro, D., and Flowers, H. M., 1961, The total synthesis of cerasine and phrenosine, J. Am. Chem. Soc. 83: 3327.

    CAS  Google Scholar 

  • Shapiro, D., and Flowers, H. M., 1962, Synthesis and configuration of natural sphingomyelins, J. Am. Chem. Soc. 84: 1047.

    CAS  Google Scholar 

  • Shapiro, D., and Sheradsky, T., 1963, Separation of diasteriomeric dihydrosphingosines. A simplified synthesis, Error! Hyperlink reference not valid .. Chem. 28: 2157.

    CAS  Google Scholar 

  • Shapiro, D., Segal, H., and Flowers, H. M., 1958a, The total synthesis of sphingosine, J. Am. Chem. Soc. 80: 1194.

    CAS  Google Scholar 

  • Shapiro, D., Segal H., and Flowers, H. M., 1958, A facile synthesis of dihydrosphingosine, J. Am. Chem. Soc. 80: 2170.

    CAS  Google Scholar 

  • Shapiro, D., Flowers, H. M., and Spector-Shefer, S., 1959a, The synthesis of dihydrosphingomyelin, J. Am. Chem. Soc. 81: 3743.

    CAS  Google Scholar 

  • Shapiro, D., Flowers, H. M., and Spector-Shefer, S., 1959b, The synthesis of sphingomyelin, J. Am. Chem. Soc. 81: 4360.

    CAS  Google Scholar 

  • Shapiro, D., Rachman, S., and Sheradsky, T., 1964, Synthesis of psychosine, J. Am. Chem. Soc. 86: 4472.

    CAS  Google Scholar 

  • Shapiro, D., Rachman, E. S., Rabinsohn, Y., and Diver-Haber, A., 1967, Synthetic studies on sphingolipids. XII. Synthesis of sphingosinephosphorylcholine, Chem. Phys. Lipids 1: 183.

    Google Scholar 

  • Slotboom, A. J., and Bonsen, P. P. M., 1970, Recent developments in the chemistry of phospholipids, Chem. Phys. Lipids 5: 301.

    Google Scholar 

  • Slotboom, A. J., de Haas, G. H., and van Deenen, L. L. M., 1967a, Chemical synthesis of plasmalogens, Chem. Phys. Lipids 1: 192.

    CAS  Google Scholar 

  • Slotboom, A. J., de Haas, G. H., and van Deenen, L. L. M., 19676, Synthesis of lysophosphoglycerides, Chem. Phys. Lipids 1: 317.

    Google Scholar 

  • Slotboom, A. J., de Haas, G. H., Bonsen, P. P. M., Burbach-Westerhuis, G. J., and van Deenen, L. L. M., 1970a, Hydrolysis of phosphoglycerides by purified lipase preparations. I. Substrate-, positional-, and stereo-specificity, Chem. Phys. Lipids 4: 15.

    CAS  Google Scholar 

  • Slotboom, A. J., de Haas, G. H., Bonsen, P. P. M., Burbach-Westerhuis, G. J., and van Deenen, L. L. M., 1970b, Hydrolysis of phosphoglycerides by purified lipase preparations. II. Preparation of unsaturated 2-monoacyl choline phosphoglycerides, Chem. Phys. Lipids 4: 30.

    CAS  Google Scholar 

  • Slotboom, A. J., Verheij, H. M., and de Haas, G. H., 1973, Simplified pathways for the preparation of some well-defined phosphoglycerides, Chem. Phys. Lipids 11: 295.

    PubMed  CAS  Google Scholar 

  • Snyder, F., 1972, Biosynthesis of alkoxylipids, in: Ether Lipids, Chemistry and Biology ( F. Snyder, ed.), pp. 121–156, Academic Press, New York and London.

    Google Scholar 

  • Sowden, J. C., 1962, a-L-Glucose and L-mannose from L-arabinose by the nitromethane synthesis, Methods in Carbohydrate Chem. 1: 132.

    Google Scholar 

  • Sowden, J. C., and Fischer, H. O. L., 1941, Synthesis of D-a,ß-diglycerides, J. Am. Chem. Soc. 63: 3244.

    CAS  Google Scholar 

  • Stanacev, N. Z., and Kates, M., 1960, Synthesis of dipalmitoyl-L-a-glycerophosphoric acid derivatives as possible intermediates for synthesis of glycerophosphatides, Can. J. Biochem. Physiol. 38: 297.

    PubMed  CAS  Google Scholar 

  • Stanacev, N. Z., Stuhne-Sekalec, L., and Domazet, Z., 1973, Enzymatic formulation of cardiolipin from phosphatidylglycerol by transphosphatidylation mechanism catalyzed by phospholipase D, Can. J. Bioche„m. 51: 747.

    CAS  Google Scholar 

  • Stegerhoek, L. J., and Verkade, P. E., 1956, Esters derived from butyl alcohol, Rec. Tray. Chim. 75: 467.

    CAS  Google Scholar 

  • Stoffel, W., 1973, Chemistry and biochemistry of sphingosine bases, Chem. Phys. Lipids 11: 318.

    PubMed  CAS  Google Scholar 

  • Stoffel, W., and Grol, M., 1974, Chemistry and biochemistry of 1-deoxysphinganine-l-phosphonate (dihydrosphingosine-l-phnsphonate), Chem. Phys. Lipids 13: 372.

    PubMed  CAS  Google Scholar 

  • Stoffel, W., and Wolff, G. D., 1966, Chemische synthese von 1–0-[3H]palmitoyl-L-glyc-erin-3-phosphat (L-3-lyso-phosphatidsaure), Z. Physiol. Chem 347: 94.

    CAS  Google Scholar 

  • Takahashi, T., Hashimoto, T., and Hara, I., 1967, Méthode rapide de préparation du cardiolipide par échange ionique, Bull. Soc. Chim. Biol. 49: 65.

    PubMed  CAS  Google Scholar 

  • Thomas, P. J., and Law, J. H., 1966, Synthesis of an unsaturated diether analog of phosphatidylethanolamine, J. Lipid Res. 7: 453.

    PubMed  CAS  Google Scholar 

  • Tinoco, J., and McIntosh, D. J., 1970, Interactions between cholesterol and lecithins in monolayers at the air—water interface, Chem. Phys. Lipids 4: 72.

    CAS  Google Scholar 

  • Tocanne, J. F., Verheij, H. M., op den Kamp, J. A. F., and van Deenen, L. L. M., 1974, Chemical and physicochemical studies of lysylphosphatidylglycerol derivatives. Occurrence of a 2’—> 3’ lysyl migration, Chem. Phys. Lipids 13: 389.

    PubMed  CAS  Google Scholar 

  • Trevelyan, W. E., 1966, Preparation of phosphatidylinositol from bakers’ yeast, J. Lipid Res. 7: 445.

    PubMed  CAS  Google Scholar 

  • Trevelyan, W. E., 1967, Removal of sphingolipid impurity from preparation of yeast phosphatidylinositol, J. Lipid Res. 8: 281.

    PubMed  CAS  Google Scholar 

  • Turner, D. L., Silver, M. J., Baczynski, E., Giordano, N., and Rodalewicz, I., 1964, Synthesis and activity in blood-clotting systems of unsaturated racemic phosphatidylserines, J. Lipid Res. 5: 616.

    PubMed  CAS  Google Scholar 

  • Turner, D. L., Silver, M. J., and Baczynski, E., 1966, The total synthesis of dilinoleoylphosphatidylserine and its activity in blood-clotting systems, Lipids 1: 439.

    PubMed  CAS  Google Scholar 

  • van Deenen, L. L. M., and de Haas, G. H., 1963, Substrate specificity of phospholipase A, Biochim. Biophys. Acta 70: 538.

    CAS  Google Scholar 

  • van Deenen, L. L. M., and de Haas, G. H., 1964, Synthesis of phosphoglycerides and some biochemical applications, Adv. Lipid Res. 2: 167.

    PubMed  Google Scholar 

  • van den Bosch, H., and van Deenen, L. L. M., 1965, Chemical structure and biochemical significance of lysolecithins from rat liver, Biochim. Biophys. Acta 106: 326.

    PubMed  Google Scholar 

  • van Gijzen, J., Hoefnagel, M. A., and Verkade, P. E., 1964, Phosphatidic acid and derivatives. 12. Synthesis of bis-ß-glycerophosphatidic acids starting from a,y-diglycerides with one or two saturated component acids, Rec. Tray. Chim. 83: 287.

    Google Scholar 

  • van Golde,• L. M. G., and van Deenen, L. L. M., 1966, The effect of dietary fat on the molecular species of lecithin from rat liver, Biochim. Biophys. Acta 125: 496.

    Google Scholar 

  • Verheij, H. M., Bonsen, P. P. M., and van Deenen, L. L. M., 1971, The chemical synthesis of two isomers of glucosaminylphosphatidylglycerol, Chem. Phys. Lipids 6: 46.

    PubMed  CAS  Google Scholar 

  • Vtorov, I. B., Serebrennikova, G. A., and Evstigneeva, R. P., 1971, Synthesis of plasmalogens with natural configuration, Tetrahedron Letters 48: 4605.

    Google Scholar 

  • Vtorov, I. B., Serebrennikova, G. A., and Evstigneeva, R. P., 1972, Complex lipids. Synthesis and study of the structure of cis-1-O-hexadec-l’-enyl-2-stearoyl-sn-glycero-3phosphoryl-N,N-dimethylethanolamine, Error! Hyperlink reference not valid .. Kh. 8: 721.

    CAS  Google Scholar 

  • Warner, H. R., and Lands, W. E. M., 1963, The configuration of the double bond in naturally occurring alkenyl ethers, J. Am. Chem. Soc. 85: 60.

    CAS  Google Scholar 

  • Wells, M. A., and Hanahan, D. J., 1969, Phospholipase A from Crotalis adamanteus venom, Methods in Enzymol. 14: 178.

    CAS  Google Scholar 

  • Weltzien, H. U., and Westphal, 0., 1967, Synthesis of choline phosphatides. IV. O-Methylated and O-acetylated lysolecithins, Ann. Chem. 709: 240.

    CAS  Google Scholar 

  • Yang, S. F., Freer, S., and Benson, A. A., 1967, Transphosphatidylation by phospholipase D, J. Biol. Chem. 242: 477.

    PubMed  CAS  Google Scholar 

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  1. Department of Biochemistry, University of Ottawa, Ottawa, Canada

    M. Kates

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  1. Laboratory of Cell Biology, National Heart and Lung Institute, Bethesda, Maryland, USA

    Edward D. Korn

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Kates, M. (1977). Synthesis of Stereoisomeric Phospholipids for Use in Membrane Studies. In: Korn, E.D. (eds) Methods in Membrane Biology. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-2910-7_3

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