Synthesis of 1-lyso-2-palmitoyl-rac-glycero-3-phosphocholine and its regioisomers and structural elucidation by NMR spectroscopy and FAB tandem mass spectrometry

Tetrahedron

Volumn 59, Issue 16, 2003, Pages 2921-2928

  Kim, Young Ah ^a   Park, Myoung Soon ^a   Kim, Young Hwan ^b   Han, So Yeop ^a  

^a Ewha Womans University   (South Korea)

^b Korea Basic Science Institute (KBSI)   (South Korea)

Author keywords

1 lysophosphatidylcholine; Acyl migration; CID (collision induced dissociation); FAB MS (fast atom bombardment mass spectrometry); MS MS (tandem mass spectrometry); NMR (nuclear magnetic resonance); Regioisomer

Indexed keywords

1 LYSO 2 PALMITOYLGLYCERO 3 PHOSPHOCHOLINE; 1 LYSO 3 PALMITOYLGLYCERO 2 PHOSPHOCHOLINE; 1 PALMITOYL 2 LYSOGLYCERO 3 PHOSPHOCHOLINE; BROMINE; DIMETHYL SULFOXIDE; ETHYLENE CHLOROPHOSPHITE; ETHYLENE DERIVATIVE; GLYCEROL; HYDROXYL GROUP; LYSOPHOSPHATIDYLCHOLINE; TRIMETHYLAMINE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; ISOMER; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SILYLATION; STEREOSPECIFICITY; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY;

EID: 0037437112     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00282-5     Document Type: Article

References (35)

1. Shin B.A., Kim Y.R., Lee I.-S., Sung C.K., Hong J., Sim C.J., Im K.S., Jung J.H. J. Nat. Prod. 62:1999;1554.
2. Min J., Lee Y.-J., Kim Y.-A., Park H.-S., Han S.-Y., Jhon G.-J., Choi W. Biochim. Biophys. Acta. 1531:2001;77.
3. Asaoka Y., Oka M., Yoshida K., Sasaki Y., Nishizuka Y. Proc. Natl Acad. Sci. USA. 89:1992;6447.
4. Yuan Y., Schoenwaelder S.M., Salem H.H., Jackson S.P. J. Biol. Chem. 271:1996;27090.
5. Yuan Y., Jackson S.P., Newnham H.H., Mitchell C.A., Salem H.H. Blood. 86:1995;4166.
6. Wong J.T., Tran K., Pierce G.N., Chan A.C., Choy P.C. J. Biol. Chem. 273:1998;6830.
7. Durante W., Liao L., Peyton K.J., Schafer A.I. J. Biol. Chem. 272:1997;30154.
8. Pete M.J., Exton J.H. Biochim. Biophys. Acta. 1256:1995;367.
9. Thiès F., Delachambre M.C., Bentejac M., Lagarde M., Lecerf J. J. Neurochem. 59:1992;1110.
10. Hirano K., Tanaka A., Yoshizumi K., Tanaka T., Satouchi K. J. Biochem. 122:1997;1160.
11. Bernoud N., Fenart L., Molière P., Dehouck M.-P., Lagarde M., Cecchelli R., Lecerf J. J. Neurochem. 72:1999;338.
12. Morash S.C., Cook H.W., Spence M.W. Biochim. Biophys. Acta. 1004:1989;221.
13. (a) Kazi A.B., Shidmand S., Hajdu J. J. Org. Chem. 64:1999;9337
14. (b) Zhu C., Morimoto T., Nakajima S., Nitoda T., Baba N. J. Nat. Prod. 64:2001;98
15. (c) Das A.K., Hajra A.K. J. Lipid Res. 36:1995;2459
16. (d) Deng Y., Salomon R.G. J. Org. Chem. 63:1998;7789.
17. (a) Chandrakumar N.S., Hajdu J. J. Org. Chem. 48:1983;1197
18. (b) Piantadosi C., Marasco C.J., Morris-Natschke S.L., Meyer K.L., Gumus F., Surles J.R., Ishaq K.S. J. Med. Chem. 34:1991;1408
19. (c) Surles J.R., Morris-Natschke S., Marx M.H., Piantadosi C. Lipids. 28:1993;55
20. (d) Baburina I., Jackowski S. J. Biol. Chem. 273:1998;2169.
21. Bouzide A., Sauvé G. Tetrahedron Lett. 38:1997;5945.
22. Han S.-Y., Cho S.-H., Kim S.-Y., Seo J.-T., Moon S.-J., Jhon G.-J. Bioorg. Med. Chem. Lett. 9:1999;59.
23. (a) Byun H.-S., Sadlofsky J.A., Bittman R. J. Org. Chem. 63:1998;2560
24. (b) Byun H.-S., Erukulla R.K., Bittman R. J. Org. Chem. 59:1994;6495.
25. Burgos C.E., Ayer D.E., Johnson R.A. J. Org. Chem. 52:1987;4973.
26. Erukulla R.K., Byun H.-S., Bittman R. J. Org. Chem. 60:1995;7706.
27. Limb J.-K., Kim Y.H., Han S.-Y., Jhon G.-J. J. Lipid Res. 40:1999;2169.
28. Murari R., Abd El-Rahman M.M.A., Wedmid Y., Parthasarathy S., Baumann W.J. J. Org. Chem. 47:1982;2158.
29. Sacchi R., Addeo F., Paolillo L. Magn. Reson. Chem. 35:1997;S133.
30. (a) Kim Y.H., Yoo J.S., Kim M.S. Bull. Kor. Chem. Soc. 18:1997;874
31. (b) Kim Y.H., Choi J.-S., Yoo J.S., Park Y.-M., Kim M.S. Anal. Biochem. 267:1999;260
32. (c) Kim Y.H., So K.-Y., Limb J.-K., Jhon G.-J., Han S.-Y. Rapid Commun. Mass Spectrom. 14:2000;2230
33. (d) Kim Y.H., Gil J.H., Hong J., Yoo J.S. Microchem. J. 68:2001;143.
34. Han X., Gross R.W. J. Am. Chem. Soc. 118:1996;451.
35. Kim Y.H., Yoo J.S., Lee C.H., Goo Y.M., Kim M.S. J. Mass Spectrom. 32:1997;968.