Synthesis of 2′-C-α-(hydroxyalkyl) and 2′-C-α- alkylcytidine phosphoramidites: Analogues for probing solvent interactions with RNA

Journal of Organic Chemistry

Volumn 72, Issue 4, 2007, Pages 1198-1210

  Li, Nan Sheng ^a   Piccirilli, Joseph A ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTIDINE; PHOSPHORAMIDITES; URIDINE;

HYDROXYLATION; OLEFINS; ORGANIC SOLVENTS; RNA; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

2' C ALPHA (2 ACETOXYETHYL) N4 ACETYL 2' DEOXY 5' O (DIMETHOXYTRITYL)CYTIDINE 3' N,N DIISOPROPYL(CYANOETHYL)PHOSPHORAMIDITE; 2' C ALPHA (3 ACETOXYBUTYL) N4 ACETYL 2' DEOXY 5' O (DIMETHOXYTRITYL)CYTIDINE 3' N,N DIISOPROPYL(CYANOETHYL)PHOSPHORAMIDITE; 2' C ALPHA (3 ACETOXYPROPYL) N4 ACETYL 2' DEOXY 5' O (DIMETHOXYTRITYL)CYTIDINE 3' N,N DIISOPROPYL(CYANOETHYL)PHOSPHORAMIDITE; ALCOHOL; ALKENE; CYTIDINE DERIVATIVE; N4 ACETYL 2' C ALPHA BUTYL 2' DEOXY 5' O (DIMETHOXYTRITYL)CYTIDINE 3' N,N DIISOPROPYL(CYANOETHYL)PHOSPHORAMIDITE; N4 ACETYL 2' DEOXY 5' O (DIMETHOXYTRITYL) 2' C ALPHA ETHYLCYTIDINE 3' N,N DIISOPROPYL(CYANOETHYL)PHOSPHORAMIDITE; N4 ACETYL 2' DEOXY 5' O (DIMETHOXYTRITYL) 2' C ALPHA PROPYLCYTIDINE 3' N,N DIISOPROPYL(CYANOETHYL)PHOSPHORAMIDITE; NUCLEOSIDE DERIVATIVE; PHOSPHORAMIDOUS ACID DERIVATIVE; RNA; SOLVENT; UNCLASSIFIED DRUG; URIDINE; WATER; CYTIDINE; DRUG DERIVATIVE; ORGANOPHOSPHORUS COMPOUND;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR PROBE; ORGANIC CHEMISTRY; SYNTHESIS; CHEMISTRY;

CYTIDINE; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; RNA; WATER;

EID: 33846949022     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062002t     Document Type: Article

References (31)

1. Pavey, J. B. J.; Lawrence, A. J.; Potter, A. J.; Cosstick, R.; O'Neil, I. A. Tetrahedron Lett. 1998, 39, 6967.
2. Peng, C. G.; Damha, M. J. Nucleic Acids Res. 2005, 33, 7019.
3. Mesmaeker, A. D.; Lebreton, J.; Hoffmann, P.; Freier, S. M. Synlett 1993, 677.
4. Sukeda, M.; Shuto, S.; Sugimoto, I.; Ichikawa, S.; Matsuda, A J. Org. Chem. 2000, 65, 8988.
5. Fehring, V.; Knights, S.; Chan, M.-Y.; O'Neil, I. A.; Cosstick, R. Org. Biomol. Chem. 2003, 1, 123.
6. Hermanson, G. T. Bioconjugate Techniques; Academic Press: San Diego, CA, 1995.
7. Goodwin, J. T.; Osborne, S. E.; Scholle, E. J.; Glick, G. D. J. Am. Chem. Soc. 1996, 118, 5207.
8. Wibley, J. E. A.; Waters, T. R.; Haushalter, K.; Verdine, G. L.; Pearl, L. Mol. Cells 2003, 11, 1647.
9. Jarrell, K. A.; Dietrich, R. C.; Perlman, P. S. Mol. Cell. Biol. 1988, 8, 2361.
10. Griffin, E. A.; Qin, P. Z.; Michels, W. J.; Pyle, A. M. Chem. Biol. 1995, 2, 761.
11. Gordon, P. M.; Fong, R.; Deb, S.; Li, N.-S.; Schwans, J. P.; Ye, J.-D.; Piccirilli, J. A. Chem. Biol. 2004, 11, 237.
12. Li, N.-S.; Piccirilli, J. A. J. Org. Chem. 2003, 68, 6799.
13. Li, N.-S.; Piccirilli, J. A. J. Org. Chem. 2004, 69, 4751.
14. Grotli, M.; Undheim, K. Acta Chem. Scand. 1995, 49, 217.
15. Beigelman, L.; Karpeisky, A.; Matulic-Adamic, J.; Haeberli, P.; Sweedler, D.; Usman, N. Nucleic Acids Res. 1995, 23, 4434.
16. Lawrence, A. J.; Pavey, J. B. J.; O'Neil, I. A.; Cosstick, R. Tetrahedron Lett. 1995, 36, 6341.
17. Lawrence, A. J.; Pavey, J. B. J.; Cosstick, R.; O'Neil, I. A. J. Org. Chem. 1996, 61, 9213.
18. Rhei, S. O.; Pfleiderer, W. Nucleosides Nucleotides 1992, 11, 835.
19. Robins, M. J.; Wilson, J. S.; Hansske, F. J. Am. Chem. Soc. 1983, 105, 4059.
20. Serebryany, V.; Beigelman, L. N. Tetrahedron Lett. 2002, 43, 1983.
21. Tang, X.-Q.; Liao, X.; Piccirilli, J. A. J. Org. Chem. 1999, 64, 747.
22. Furusawa, K.; Ueno, K.; Katsura, T. Chem. Lett. 1990, 97.
23. Corey, E. J.; Nagata, R. Tetrahedron Lett. 1987, 28, 5391.
24. Nakamura, E.; Machii, D.; Inubushi, T. J. Am. Chem. Soc. 1989, 111, 6849.
25. Christensen, L. F.; Broom, A. D. J. Org. Chem. 1972, 37, 3398.
26. Cicero, D. O.; Neuner, P. J. S.; Franzese, O.; D'Onofrio, C.; Iribarren, A. M. Bioorg. Med. Chem. Lett. 1994, 4, 861.
27. Iino, T.; Yoshimura, Y.; Matsuda, A. Tetrahedron 1994, 50, 10397.
28. Xi, Z.; Agback, P.; Plavec, J.; Sandstrom, A.; Chattopadhyaya, J. Tetrahedron 1992, 48, 349.
29. Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Academic Press: San Diego, CA, 1988.
30. Kabalka, G. W.; Li, N.-S.; Pace, R. D. Synth. Commun. 1995, 25, 2135.
31. Lane, C. F. Chem. Rev. 1976, 76, 773.