Electrospray tandem mass-spectrometric analysis of diastereo- and stereoisomeric pyrimidine nucleoside analogues based on the 1,3-dihydrobenzo[c] furan core

Carbohydrate Research

Volumn 338, Issue 22, 2003, Pages 2311-2324

  Len, Christophe ^a   Mackenzie, Grahame ^b   Ewing, David F ^b   Sheppard, George ^c   Banoub, Joseph ^c,d  

^a UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

^b UNIVERSITY OF HULL   (United Kingdom)

^c FISHERIES AND OCEANS CANADA   (Canada)

^d MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

Author keywords

Electrospray tandem mass spectrometry; Structural characterization; Thymine diastereoisomers; Uracil enantiomers of 1,3 dihydrobenzo c furan nucleosides

Indexed keywords

DISSOCIATION; MASS SPECTROMETRY; STEREOCHEMISTRY;

ELECTROSPRAY SPECTRA;

ISOMERS;

FURAN DERIVATIVE; PYRIMIDINE NUCLEOSIDE DERIVATIVE; URACIL DERIVATIVE;

ARTICLE; DIASTEREOISOMER; DISSOCIATION; DRUG STRUCTURE; ENANTIOMER; ENERGY; MASS SPECTROMETRY; MOLECULAR BIOLOGY; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOISOMERISM; TANDEM MASS SPECTROMETRY;

EID: 0142183304     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2003.08.017     Document Type: Article

References (29)

1. Mitsuya H., Weinhol K.J., Furman P.A., St Clair M.H., Nusinoff-Lejrman S., Gallo R.C., Bolognesi D.P., Barry D.W., Broder S. Proc. Natl. Acad. Sci. USA. 82:1985;7096-7100.
2. Cooney D.A., Dalal M., Mitsuya H., McMahon J.B., Nadkarni M., Balzarini J., Broder S., Johns D.G. Biochem. Pharmacol. 35:1986;2065-2068.
3. Ahluwalia G., Cooney D.A., Mitsuya H., Fridland A., Flora K.P., Hao Z., Dalal M., Broder S., Johns D.G. Biochem. Pharmacol. 35:1986;3797-3800.
4. Coates J.A., Cammack N.S., Jenkinson H.J., Jowett M.I., Pearson B.A., Pen C.R., Rouse P.L., Viner K.C., Cameron J.M. Antimicrob. Agents Chemother. 36:1992;733-739.
5. Balzarini J., Kang C.J., Dalal M., Herdewijn P., De Clercq E., Broder S., Johns D.G. Mol. Pharmacol. 32:1987;162-167.
6. Lea A.P., Faulds D. Drugs. 51:1996;846-864.
7. Simpson M.V., Chin C.D., Keilbaugh S.A., Lin T.S., Prusoff W.H. Biochem. Pharmacol. 38:1989;1033-1036.
8. Ewing D.F., Fahmi N., Len C., Mackenzie G., Ronco G., Villa P., Shaw G. Collect. Czech. Chem. Commun. 61:1996;S145-S146.
9. Ewing D.F., Fahmi N., Len C., Mackenzie G., Ronco G., Villa P., Shaw G. Nucleosides Nucleotides. 18:1999;2613-2630.
10. Ewing D.F., Fahmi N., Len C., Mackenzie G., Pranzo A. J. Chem. Soc. Perkin Trans. I. 21:2000;3561-3565.
11. Ewing D.F., Len C., Mackenzie G., Ronco G., Villa P. Tetrahedron: Asymmetry. 11:2000;4995-5002.
12. Humble R.W., Mackenzie G., Shaw G. Nucleosides Nucleotides. 3:1984;363-367.
13. Russ P.L., Hegedus L., Kelly J.A., Barchi J.J., Marquez V.E. Nucleosides Nucleotides. 11:1992;351.
14. Banoub J., Mackenzie G., Descotes G., Humble R.W., Shaw G., Becchi M., Fraisse D. Biomed. Environ. Mass Spectrom. 19:1990;97-99.
15. Banoub J., Becchi M., Descotes G., Fraisse D., Humble R.W., Mackenzie G. J. Carbohydr. Chem. 11:(4):1992;471-484.
16. Banoub J., Gentil E., Tber B., Fahmi N.E., Ronco G., Villa P., Mackenzie G. Spectroscopy Int. J. 12:1994;69-83.
17. Chauvin C., Thibault P., Plusquellec D., Banoub J. J. Carbohydr. Chem. 12:1993;459-475.
18. Baczko C., Nugier-Chauvin C., Banoub J., Thibault P., Plusquellec D. Carbohydr. Res. 269:1995;79.
19. Gentil E., Lesimple A., Le Bigot Y., Delmas M., Banoub J. Rapid Commun. Mass Spectrom. 8:1994;869-875.
20. Banoub J., Becchi M., Lafont D., Descotes G., Fraisse D. Rapid Commun. Mass Spectrom. 4:1990;536-540.
21. Helleur R.J., Thibault P., Shaw D.H., Banoub J. Org. Mass Spectrom. 27:1992;967-973.
22. Banoub J., Thibault P., Goueth P.Y., Ronco G., Villa P. J. Mass Spectrom. 32:1997;109-121.
23. Gentil E., Banoub J. J. Mass Spectrom. 31:1996;83-94.
24. Bateman K.P., Banoub J., Thibault P. Electrophoresis. 17:1996;1818-1828.
25. Banoub J., Combden S., Miller-Banoub J., Sheppard G., Hodder H. Nucleosides Nucleotides. 18:(11&12):1999;2751-2768.
26. Fenn J.B., Mann M., Meng C.K., Wong S.F., Withehouse C.M. Science. 246:1989;64-71.
27. Busch K.L., Glish G.L., McLuckey S. Mass Spectrometry-Mass Spectrometry: Techniques and Applications of Tandem Mass Spectrometry. 1988;217 VCM Publisher.
28. McLafferty F.W. Tandem Mass Spectrometry. 1983;532 Wiley Interscience, New York.
29. Crow F.W., Tomer B.K., Gross M.L., McCloskey J.A., Bergstrom D.E. Anal. Biochem. 139:1984;243-262.