Highly selective and sensitive template-directed photoligation of DNA via 5-carbamoylvinyl-2′-deoxycytidine

Organic Letters

Volumn 8, Issue 22, 2006, Pages 5049-5051

  Yoshimura, Yoshinaga ^a,b   Okamura, Daisuke ^a   Ogino, Masayuki ^a   Fujimoto, Kenzo ^a,b  

^a JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5 CARBAMOYLVINYL 2' DEOXYCYTIDINE; 5-CARBAMOYLVINYL-2'-DEOXYCYTIDINE; DEOXYCYTIDINE; DNA; DRUG DERIVATIVE; OLIGONUCLEOTIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; FLUORESCENCE; NUCLEOTIDE SEQUENCE; PHOTOCHEMISTRY;

BASE SEQUENCE; DEOXYCYTIDINE; DNA; FLUORESCENCE; MOLECULAR STRUCTURE; OLIGONUCLEOTIDES; PHOTOCHEMISTRY;

EID: 33750907113     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0619462     Document Type: Article

References (21)

1. (a) Landegren, U.; Kaiser, R.; Sanders, J.; Hood, L. Science 1988, 241, 1077-1080.
2. (b) Luo, J.; Bergstrom, D. E.; Barany, F. Nucleic Acids Res. 1996, 24, 3071-3078.
3. Xu, Y.; Karalkar, N. B.; Kool, E. T. Nat. Biotechnol. 2001, 19, 148-152.
4. McCarthy, J. J.; Hilfiker, R. Nat. Biotechnol. 2000, 18, 505-508.
5. (a) Zhong, X. B.; Reynolds, R.; Kidd, J. R.; Kidd, K. K.; Jenison, R.; Marlar, R. A.; Ward, D. C. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 11559-11564.
6. (b) Deng, J.-Y.; Zhang, X.-E.; Mang, Y.; Zhang, Z.-P.; Zhou, Y.-F.; Liu, Q.; Lu, H.-B.; Fu, Z.-J. Biosens. Bioelectron. 2004, 19, 1277-1283.
7. (a) Yoshimura, Y.; Noguchi, Y.; Sato, H.; Fujimoto, K. ChemBioChem 2006, 7, 598-601.
8. (b) Ogasawara, S.; Fujimoto, K. Angew. Chem., Int. Ed. 2006, 45, 4512-4515.
9. (a) Fujimoto, K.; Matsuda, S.; Takahashi, N.; Saito, I. J. Am. Chem. Soc. 2000, 122, 5646-5647.
10. (b) Fujimoto, K.; Ogawa, N.; Hayashi, M.; Matsuda, S.; Saito, I. Tetrahedron Lett. 2000, 41, 9437-9440.
11. (c) Saito, I.; Miyauchi, Y.; Saito, Y.; Fujimoto, K. Tetrahedron Lett. 2005, 46, 97-99.
12. (d) Ogasawara, S.; Fujimoto, K. ChemBioChem 2005, 6, 1756-1760.
13. (e) Fujimoto, K.; Matsuda, S.; Yoshimura, Y.; Matsumura, T.; Hayashi, M.; Saito, I. Chem. Commun. 2006, 3223-3225.
14. Fujimoto, K.; Matsuda, S.; Ogawa, N.; Hayashi, M.; Saito, I. Tetrahedron Lett. 2000, 41, 6451-6454.
15. (a) Xu, Y.-Z.; Zheng, Q.; Swann, P. F. J. Org. Chem. 1992, 57, 3839-3845.
16. (b) Scherr, M.; Klebba, C.; Häner, R.; Ganser, A.; Engels, J. W. Bioorg. Med. Chem. Lett. 1997, 7, 1791-1796.
17. -1.
18. 2) at 0°C for 20 min. After irradiation, the progress of the photoreaction was monitored by CGE. The yield was calculated on the basisof ODN1(C).
19. VC-T): Φ = 0.092.
20. +], found 3436.08.
21. When ODN containing 7-carboxyvinyl-7-deaza-2′-deoxyguanosine at the 5′ end was photoirradiated with ODNs containing a pyrimidine base at the 3′ end in the presence of template ODN, efficient photoligation was observed without any byproduct formation.