Synthesis of oligonucleotides containing bulky adducts at guanine N2 via the phosphoramidite of O2-triflate-O6-NPE 2'-deoxyxanthosine

Tetrahedron Letters

Volumn 41, Issue 19, 2000, Pages 3555-3558

  Cooper, Monica D ^a   Hodge, Richard P ^a   Tamura, Pamela J ^a   Wilkinson, Amanda S ^a   Harris, Constance M ^a   Harris, Thomas M ^a  

^a VANDERBILT UNIVERSITY   (United States)

Author keywords

Nucleic acids; Nucleosides; Polycyclic aromatic compounds; Purines

Indexed keywords

GUANINE DERIVATIVE; NUCLEIC ACID; NUCLEOSIDE; OLIGONUCLEOTIDE; POLYCYCLIC AROMATIC COMPOUND; PURINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034611937     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00461-5     Document Type: Article

References (22)

1. Baertschi, S. W.; Raney, K. D.; Stone, M. P.; Harris, T. M. J. Am. Chem. Soc. 1988, 110, 7929-7931.
2. Cosman, M.; Ibanez, V.; Geacintov, N. E.; Harvey, R. G. Carcinogenesis 1990, 11, 1667-1672.
3. Lee, H.; Hinz, M.; Stezowski, J. J.; Harvey, R. G. Tetrahedron Lett. 1990, 31, 6773-6776.
4. Custer, L.; Zajc, B.; Sayer, J. M.; Cullinane, C.; Phillips, D. R.; Cheh, A. M.; Jerina, D. M.; Bohr, V. A.; Mazur, S. J. Biochemistry 1999, 38, 569-581.
5. Steinbrecher, T.; Becker, A.; Stezowski, J. J.; Oesch, F.; Seidel, A. Tetrahedron Lett. 1993, 34, 1773-1774.
6. Harris, C. M.; Zhou, L.; Strand, E. A.; Harris, T. M. J. Am. Chem. Soc. 1991, 113, 4328-4329.
7. Harris, T. M.; Harris, C. M.; Kim, S. J.; Han, S.; Kim, H.-Y.; Zhou, L. Polycyclic Aromatic Compounds 1994, 6, 9-16.
8. Kim, S. J.; Jajoo, H. K.; Kim, H.-Y.; Zhou, L.; Horton, P.; Harris, C. M.; Harris, T. M. Bioorg. Med. Chem. 1995, 3, 811-822.
9. Page, J. E.; Zajc, B.; Oh-hara, T.; Lakshman, M. K.; Sayer, J. M.; Jerina, D. M.; Dipple, A. Biochemistry 1998, 37, 9127-9137.
10. Steinbrecher, T.; Wameling, C.; Oesch, F.; Seidel, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 404-406.
11. Edwards, C.; Boche, G.; Steinbrecher, T.; Scheer, S. J. Chem. Soc., Perkin Trans. 1 1997, 1887-1893.
12. Büchi, G.; Fowler, K. W.; Nadzan, A. M. J. Am. Chem. Soc. 1982, 104, 544-547.
13. Mitsunobu, O. Synthesis 1981, 1-28.
14. Trichtinger, T.; Charubala, R.; Pfleiderer, W. Tetrahedron Lett. 1983, 24, 711-714.
15. Zajc, B.; Lakshman, M. K.; Sayer, J. M.; Jerina, D. M. Tetrahedron Lett. 1992, 33, 3409-3412.
16. Eritja, R.; Horowitz, D. M.; Walker, P. A.; Ziehler-Martin, J. P.; Boosalis, M. S.; Goodman, M. F.; Itakura, K.; Kaplan, B. E. Nucleic Acids Res. 1986, 14, 8135-8153.
17. f 6, 0.95; 7, 0.35; monobutyrates, 0.80, 0.85; deacylated 5, 0.2.
18. Jones, R. Oligonucleotide Synthesis, A Practical Approach; Gait, M. J., Ed.; IRL Press: Washington, DC, 1984; pp. 22-34.
19. Barone, A. D.; Tang, J.-Y.; Caruthers, M. H. Nucleic Acids Res. 1984, 12, 4051-4061.
20. Bannwarth, W.; Trzeciak, A. Helv. Chim. Acta 1987, 70, 175-186.
21. +, found 550.0867.
22. McNees, A. G.; O'Donnell, M.; Horton, P. J.; Kim, H.-Y.; Kim, S. J.; Harris, C. M.; Harris, T. M.; Lloyd, R. S. J. Biol. Chem. 1997, 272, 33211-33219.