Efficient desulfurization of 2-thiopyrimidine nucleosides to the corresponding 4-pyrimidinone analogues using trans-2-(phenylsulfonyl)-3- phenyloxaziridine

Tetrahedron Letters

Volumn 45, Issue 36, 2004, Pages 6729-6731

  Sochacka, Elzbieta ^a   Fra̧tczak, Iwona ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

2 Thiopyrimidine nucleosides; 4 Pyrimidinone 1 d ribosides; Oxaziridine; Oxidative desulfurization

Indexed keywords

2 (PHENYLSULFONYL) 3 PHENYLOXAZIRIDINE; 4 PYRIMIDINONE 1 BETA DEXTRO RIBOSIDE; 4 PYRIMIDINONE DERIVATIVE; MONOMER; NUCLEOSIDE DERIVATIVE; OLIGONUCLEOTIDE; OXAZIRIDINE DERIVATIVE; PHOSPHORAMIDOUS ACID; PHOSPHORUS DERIVATIVE; SULFUR ACID DERIVATIVE; SULFUR DIOXIDE; UNCLASSIFIED DRUG;

ARTICLE; DESULFURIZATION; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; OXIDATION;

EID: 4344650914     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.07.052     Document Type: Article

References (27)

1. R.A. Zimmermann, M.J. Gait, and M.J. Moore H. Grosjean R. Benne Modification and Editing of RNA 1998 ASM Washinghton, DC 59 84 Chapter IV
2. D.J. Earnshaw, and M.J. Gait Biopolymers 48 1998 39 55
3. S. Verma, and F. Eckstein Annu. Rev. Biochem. 67 1998 99 134
4. J.A. Grasby, and M.J. Gait Biochimie 76 1994 1223 1234
5. D.R. Davis H. Grosjean R. Benne Modification and Editing of RNA 1998 ASM Washinghton, DC 85 102 Chapter V
6. Y. Yamamoto, S. Yokoyama, T. Miyazawa, K. Watanabe, and S. Higuchi FEBS Lett. 157 1983 95 99
7. H. Sierzputowska-Gracz, E. Sochacka, A. Malkiewicz, K. Kuo, C. Gehrke, and P.F. Agris J. Am. Chem. Soc. 109 1987 7171 7177
8. R.K. Kumar, and D.R. Davis Nucleic Acids Res. 25 1997 1272 1280
9. S.M. Testa, M.D. Disney, D.H. Turner, and R. Kierzek Biochemistry 38 1997 16655 16662
10. K. Shohda, I. Okamoto, S. Wada, K. Seio, and M. Sekine Bioorg. Med. Chem. Lett. 10 2000 1795 1798
11. T. Ogihara, and O. Mitsunobu Chemistry Lett. 1982 1621 1624
12. S.B. Rajur, and L.W. McLaughlin Tetrahedron Lett. 33 1992 6081 6084
13. R.G. Kuimelis, and K.P. Nambiar Tetrahedron Lett. 34 1993 3813 3816
14. R. Saladino, E. Mincione, C. Cearsini, and M. Mezzetti Tetrahedron 52 1996 6759 6780
15. B. Masquida, and E. Westhof RNA 6 2000 9 15
16. K. Takai, and S. Yokoyama Nucleic Acids Res. 31 2003 6383 6391
17. F.A. Davis, and A.C. Sheppard Tetrahedron 45 1989 5703 5742
18. T. Wada, Y. Sato, F. Honda, S. Kawahara, and M. Sekine J. Am. Chem. Soc. 119 1997 12710 12721
19. D.A. Gianolio, and L.W. McLaughlin Nucleos. Nucleot. 18 1999 1751 1769
20. E. Sochacka Nucleos. Nucleot. Nucleic Acids 20 2001 1871 1879
21. H. Vorbruggen Chem. Ber. 114 1981 1279 1286
22. -
23. J.H. Karchmer The Analytical Chemistry of Sulfur and its Compounds 1970 Wiley-Interscience New York pp 163-167
24. P.F. Agris, A. Malkiewicz, A. Kraszewski, K. Everett, B. Nawrot, E. Sochacka, J. Jankowska, and R. Guenther Biochimie 77 1995 1272 1280
25. R.K. Kumar, and D.R. Davis Nucleic Acids Res. 25 1997 6383 6391
26. M.J. Dahma, and K.K. Ogilvie Methods Mol. Biol. 20 1993 81 115
27. +