Skip to main content
Proceedings of the National Academy of Sciences of the United States of America logoLink to Proceedings of the National Academy of Sciences of the United States of America
. 1977 Oct;74(10):4315–4319. doi: 10.1073/pnas.74.10.4315

Glycerophospholipid synthesis: improved general method and new analogs containing photoactivable groups.

C M Gupta, R Radhakrishnan, H G Khorana
PMCID: PMC431931  PMID: 270675

Abstract

Current methods for phospholipid synthesis involving acylation of sn-glycero-3-phosphorylcholine, lysolecithins, and related glycerophosphate esters are not satisfactory. With N,N-dimethyl-4-aminopyridine as a catalyst and moderate amounts of fatty acid anhydrides (1.2-1.5 mol equiv per OH group), diacyl or 1,2-mixed diacylphosphatidylcholines, N-protected phosphatidylethanolamines, and phosphatide acids now can be conveniently prepared in high yields (75-90%). New phospholipids containing photoactivable groups, such as trifluorodiazopropionyl, diazirinophenoxy, 2-nitro-4-azidophenoxy, m-azidophenoxy, and alpha, beta-unsaturated keto groups, in the fatty acyl chains have been prepared. These phospholipids are of interest in studies of lipid-lipid and lipid-protein interactions in biological membranes.

Full text

PDF
4317

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. AMES B. N., DUBIN D. T. The role of polyamines in the neutralization of bacteriophage deoxyribonucleic acid. J Biol Chem. 1960 Mar;235:769–775. [PubMed] [Google Scholar]
  2. Aneja R., Chadha J. S. Acyl-chloro-deoxyglycerophosphorylcholines: structure of the so-called cyclic lysolecithins. Biochim Biophys Acta. 1971 Jun 8;239(1):84–91. doi: 10.1016/0005-2760(71)90196-2. [DOI] [PubMed] [Google Scholar]
  3. BAER E., BUCHNEA D. Synthesis of saturated and unsaturated L-alpha-lecithins; acylation of the cadmium chloride compound of L-alpha-glycerylphosphorylcholine. Can J Biochem Physiol. 1959 Aug;37(8):953–959. [PubMed] [Google Scholar]
  4. BANDURSKI R. S., AXELROD B. The chromatographic identification of some biologically important phosphate esters. J Biol Chem. 1951 Nov;193(1):405–410. [PubMed] [Google Scholar]
  5. Boss W. F., Kelley C. J., Landsberger F. R. A novel synthesis of spin label derivatives of phosphatidylcholine. Anal Biochem. 1975 Mar;64(1):289–292. doi: 10.1016/0003-2697(75)90432-7. [DOI] [PubMed] [Google Scholar]
  6. Chakrabarti P., Khorana G. A new approach to the study of phospholipid-protein interactions in biological membranes. Synthesis of fatty acids and phospholipids containing photosensitive groups. Biochemistry. 1975 Nov 18;14(23):5021–5033. doi: 10.1021/bi00694a001. [DOI] [PubMed] [Google Scholar]
  7. Chang Y. Y., Kennedy E. P. Biosynthesis of phosphatidyl glycerophosphate in Escherichia coli. J Lipid Res. 1967 Sep;8(5):447–455. [PubMed] [Google Scholar]
  8. Chowdhry V., Vaughan R., Westheimer F. H. 2-diazo-3,3,3-trifluoropropionyl chloride: reagent for photoaffinity labeling. Proc Natl Acad Sci U S A. 1976 May;73(5):1406–1408. doi: 10.1073/pnas.73.5.1406. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Cubero Robles E., van den Berg D. Synthesis of lecithins by acylation of O-(sn-glycero-3-phosphoryl) choline with fatty acid anhydrides. Biochim Biophys Acta. 1969 Dec 17;187(4):520–526. doi: 10.1016/0005-2760(69)90049-6. [DOI] [PubMed] [Google Scholar]
  10. Goswami S. K., Frey C. F. Spray detection of phospholipids on thin-layer chromatograms. J Lipid Res. 1971 Jul;12(4):509–510. [PubMed] [Google Scholar]
  11. Greenberg G. R., Chakrabarti P., Khorana H. G. Incorporation of fatty acids containing photosensitive groups into phospholipids of Escherichia coli. Proc Natl Acad Sci U S A. 1976 Jan;73(1):86–90. doi: 10.1073/pnas.73.1.86. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. HANES C. S., ISHERWOOD F. A. Separation of the phosphoric esters on the filter paper chromatogram. Nature. 1949 Dec 31;164(4183):1107-12, illust. doi: 10.1038/1641107a0. [DOI] [PubMed] [Google Scholar]
  13. Keana J. F., Ertle A. R. Stearoyl paratoluenesulfonate. A powerful acylating agent for lipid synthesis. Chem Phys Lipids. 1976 Nov;17(4):402–406. doi: 10.1016/0009-3084(76)90041-4. [DOI] [PubMed] [Google Scholar]
  14. Lapidot Y., Barzilay I., Hajdu J. The synthesis of diacyl-dl-(and-L-) alpha-glycerol phosphate. Chem Phys Lipids. 1969 Apr;3(2):125–134. doi: 10.1016/0009-3084(69)90002-4. [DOI] [PubMed] [Google Scholar]
  15. Pugh E. L., Kates M. A simplified procedure for synthesis of di-[14C]acyl-labeled lecithins. J Lipid Res. 1975 Sep;16(5):392–394. [PubMed] [Google Scholar]
  16. Selinger Z., Lapidot Y. Synthesis of fatty acid anhydrides by reaction with dicyclohexylcarbodiimide. J Lipid Res. 1966 Jan;7(1):174–175. [PubMed] [Google Scholar]
  17. Slotboom A. J., Verheij H. M., De Haas G. H. Simplified pathways for the preparation of some well-defined phosphoglycerides. Chem Phys Lipids. 1973 Dec;11(4):295–317. doi: 10.1016/0009-3084(73)90067-4. [DOI] [PubMed] [Google Scholar]
  18. WOLFENDEN R., RAMMLER D. H., LIPMANN F. ON THE SITE OF ESTERIFICATION OF AMINO ACIDS TO SOLUBLE RNA. Biochemistry. 1964 Mar;3:329–338. doi: 10.1021/bi00891a006. [DOI] [PubMed] [Google Scholar]
  19. Warner T. G., Benson A. A. An improved method for the preparation of unsaturated phosphatidylcholines: acylation of sn-glycero-3-phosphorylcholine in the presence of sodium methylsulfinylmethide. J Lipid Res. 1977 Jul;18(4):548–552. [PubMed] [Google Scholar]

Articles from Proceedings of the National Academy of Sciences of the United States of America are provided here courtesy of National Academy of Sciences

RESOURCES