Synthesis of phosphatidylcholine: An improved method without using the cadmium chloride complex of sn-glycero-3-phosphocholine

Chemistry and Physics of Lipids

Volumn 137, Issue 1-2, 2005, Pages 94-99

  Ichihara, Ken'ichi ^a   Iwasaki, Hitomi ^a   Ueda, Kaori ^a   Takizawa, Ryoko ^a   Naito, Hideko ^a   Tomosugi, Mitsuhiro ^a  

^a KYOTO PREFECTURAL UNIVERSITY   (Japan)

Author keywords

Cadmium; Phosphatidylcholine; sn Glycero 3 phosphocholine; Synthesis

Indexed keywords

ACID ANHYDRIDE; CADMIUM CHLORIDE; DICYCLOHEXYLCARBODIIMIDE; GLYCEROPHOSPHATE; PHOSPHATIDYLCHOLINE; PHOSPHORYLCHOLINE; PYRIDINE DERIVATIVE;

ACYLATION; ADSORPTION; ARTICLE; CATALYST; COLUMN CHROMATOGRAPHY; FATTY ACID SYNTHESIS; LIPID ANALYSIS; PHOSPHOLIPID SYNTHESIS; PRIORITY JOURNAL;

4-AMINOPYRIDINE; ACYLATION; ANIMALS; CADMIUM CHLORIDE; CATALYSIS; CHROMATOGRAPHY; DIATOMACEOUS EARTH; EGG YOLK; FATTY ACIDS; GLYCERYLPHOSPHORYLCHOLINE; MASS SPECTROMETRY; PHOSPHATIDYLCHOLINES; PHOSPHORYLCHOLINE;

EID: 26044441614     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2005.06.001     Document Type: Article

References (33)

1. K. Aoshima Epidemiology of renal tubular dysfunction in the inhabitants of a cadmium-polluted area in the Jinzu river basin in Toyama prefecture Tohoku J. Exp. Med. 152 1987 151 172
2. E. Baer, and M. Kates l-α-Glycerylphosphorylcholine J. Am. Chem. Soc. 70 1948 1394 1399
3. P.G. Barton, and F.D. Gunstone Hydrocarbon chain packing and molecular motion in phospholipid bilayers formed from unsaturated lecithins J. Biol. Chem. 250 1975 4470 4476
4. G. Borsotti, G. Guglielmetti, S. Spera, and E. Battistel Synthesis of phosphatidylcholine containing ricinoleic acid Tetrahedron 57 2001 10219 10227
5. H. Brockerhoff, and M. Yurkowski Simplified preparation of l-α-glyceryl phosphoryl choline Can. J. Biochem. 43 1965 1777
6. J.S. Chada Preparation of crystalline l-α-glycerophosphorylcholine- cadmium chloride adduct from commercial egg lecithin Chem. Phys. Lipids 4 1970 104 108
7. E. Cubero Robles, and D. Van den Berg Synthesis of lecithins by acylation of O-(sn-glycero-3-phosphoryl) choline with fatty acid anhydrides Biochim. Biophys. Acta 187 1969 520 526
8. P.J. Davis, and K.M.W. Keough Differential scanning calorimetric studies of aqueous dispersions of mixtures of cholesterol with some mixed-acid and single-acid phosphatidylcholines Biochemistry 22 1983 6334 6340
9. J.C. Dittmer, and R.L. Lester A simple, specific spray for the detection of phospholipids on thin-layer chromatograms J. Lipid Res. 5 1964 126 127
10. H. Eibl Synthesis of glycerophospholipids Chem. Phys. Lipids 26 1980 405 429
11. R. Eisler Mercury hazards from gold mining to humans, plants, and animals Rev. Environ. Contam. Toxicol. 181 2004 139 198
12. L. Friberg, C.-G. Elinder, T. Kjellstrom, and G.F. Nordberg Cadmium and Health: A Toxicological and Epidemiological Appraisal vol. III 1985 CRC Press Boca Raton
13. W.S.M. Guerts van Kessel, M. Tieman, and R.A. Demel Purification of phospholipids by preparative high pressure liquid chromatography Lipids 16 1981 58 63
14. C.M. Gupta, R. Radhakrishnan, and H.G. Khorana Glycerophospholipid synthesis: improved general method and new analogs containing photoactivable groups Proc. Natl. Acad. Sci. U.S.A. 74 1977 4315 4319
15. D.J. Hanahan l-α-Glycerylphosphorylcholine Biochem. Prep. 9 1962 55 58
16. G. Höefle, W. Steglich, and H. Vorbrüeggen 4- Dialkylaminopyridines as highly active acylation catalysts Angew. Chem. Int. Ed. Engl. 17 1978 569 583
17. K. Ichihara, A. Shibahara, K. Yamamoto, and T. Nakayama An improved method for rapid analysis of the fatty acids of glycerolipids Lipids 31 1996 535 539
18. K. Ichihara, C. Yamaguchi, H. Nishijima, and K. Saito Preparation of FAME from sterol esters J. Am. Oil Chem. Soc. 80 2003 833 834
19. R.G. Jensen, and R.E. Pitas Synthesis of some acylglycerols and phosphoglycerides Adv. Lipid Res. 14 1976 213 247
20. K.M.W. Keough, and P.J. Davis Gel to liquid-crystalline phase transitions in water dispersions of saturated mixed-acid phosphatidylcholines Biochemistry 18 1979 1453 1459
21. D.R. Kodali, D.A. Atkinson, T.G. Redgrave, and D.M. Small Synthesis and polymorphism of 1, 2-dipalmitoyl-3-acyl-sn-glycerol J. Am. Oil Chem. Soc. 61 1984 1078 1084
22. J.G. Lammers, T.J. Liefkens, and J. Van der Meer Syntheses and spectroscopic properties of α- and β-phosphatidylcholines and phosphatidylethanolamines Chem. Phys. Lipids 22 1978 293 305
23. J.T. Mason, C. Huang, and R.L. Biltonen Calorimetric investigations of saturated mixed-chain phosphatidylcholine bilayer dispersions Biochemistry 20 1981 6086 6092
24. J. Mattai, P.K. Sripada, and G.G. Shipley Mixed-chain phosphatidylcholine bilayers: structure and properties Biochemistry 26 1987 3287 3297
25. K.M. Patel, J.D. Morrisett, and J.T. Sparrow A convenient synthesis of phosphatidylcholines: acylation of sn-glycero-3-phosphocholine with fatty acid anhydride and 4-pyrrolidinopyridine J. Lipid Res. 20 1979 674 677
26. R. Radhakrishnan, R.J. Robson, Y. Takagaki, and H.G. Khorana Synthesis of modified fatty acids and glycerophospholipid analogs Methods Enzymol. 72 1981 408 433
27. O. Renkonen Breakdown of lecithin on aluminum oxide columns J. Lipid Res. 3 1962 181 183
28. D.G. Rhodes, Z. Xu, and R. Bittman Structure of polymerizable lipid bilayers. V: synthesis, bilayer structure and properties of diacetylenic ether and ester lipids Biochim. Biophys. Acta 1128 1992 93 104
29. D.N. Rhodes, and D.N. Lea Phospholipids 4. On the composition of hen's egg phospholipids Biochem. J. 65 1957 526 533
30. Z. Selinger, and Y. Lapidot Synthesis of fatty acid anhydrides by reaction with dicyclohexylcarbodiimide J. Lipid Res. 7 1966 174 175
31. K. Shiroishi, T. Kjellstrom, K. Kubota, P.E. Evrin, M. Anayama, O. Vesterberg, T. Shimada, M. Piscator, T. Iwata, and H. Nishino Urine analysis for detection of cadmium-induced renal changes, with special reference to β2-microglobulin. A cooperative study between Japan and Sweden Environ. Res. 13 1977 407 424
32. W.S. Singleton, M.S. Gray, M.L. Brown, and J.L. White Chromatographically homogeneous lecithin from egg phospholipids J. Am. Oil Chem. Soc. 42 1965 53 56
33. T.G. Warner, and A.A. Benson An improved method for the preparation of unsaturated phosphatidylcholines: acylation of sn-glycero-3-phosphorylcholine in the presence of sodium methylsulfinylmethide J. Lipid Res. 18 1977 548 552