Synthesis of oligodeoxynucleotides incorporating 2-N-carbamoylguanine and evaluation of the hybridization properties

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 3, 2009, Pages 1398-1403

  Sasami, Takeshi ^a   Odawara, Yoko ^a   Ohkubo, Akihiro ^a   Sekine, Mitsuo ^a   Seio, Kohji ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Base discrimination; Decarbamoylation; DNA duplex stability; Modified guanosine

Indexed keywords

2 N CARBAMOYLGUANINE; DOUBLE STRANDED DNA; GUANINE DERIVATIVE; OLIGODEOXYNUCLEOTIDE DERIVATIVE; PHOSPHORAMIDOUS ACID; UNCLASSIFIED DRUG;

ARTICLE; BASE PAIRING; HYBRIDIZATION; NUCLEOTIDE METABOLISM; NUCLEOTIDE SEQUENCE; REACTION ANALYSIS; THERMOSTABILITY;

BASE PAIRING; CARBAMATES; DNA; GUANINE; NUCLEIC ACID HYBRIDIZATION; OLIGODEOXYRIBONUCLEOTIDES; ORGANOPHOSPHORUS COMPOUNDS; TRANSITION TEMPERATURE;

EID: 58949087363     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.11.042     Document Type: Article

References (25)

1. SantaLucia Jr. J., Allawi H.T., and Seneviratne P.A. Biochemistry 35 (1996) 3555
2. Allawi H.T., and SantaLucia Jr. J. Biochemistry 36 (1997) 10581
3. Allawi H.T., and SantaLucia Jr. J. Biochemistry 37 (1998) 2170
4. Ebel S., Lane A.N., and Brown T. Biochemistry 31 (1992) 12083
5. Skelly J.V., Edwards K.J., Jenkins T.C., and Neidle S. Proc. Natl. Acad. Sci. U.S.A. 90 (1993) 804
6. Faibis V., Cognet J.A.H., Boulard Y., Sowers L.C., and Fazakerley G.V. Biochemistry 35 (1996) 14452
7. Timofeev E., and Mirzabekov A. Nucleic Acids Res. 29 (2001) 2626
8. Kurian K.M., Watson C.J., and Wyllie A.H. J. Pathol. 187 (1999) 267
9. Seio K., Sasami T., Ohkubo A., Ando K., and Sekine M. J. Am. Chem. Soc. 129 (2007) 1026
10. Sasami T., Odawara Y., Ohkubo A., Sekine M., and Seio K. Tetrahedron Lett. 48 (2007) 5325
11. Shoda K., Okamoto I., Wada T., Seio K., and Sekine M. Bioorg. Med. Chem. Lett. 10 (2000) 1795
12. Kamimura T., Tsuchiya K., Urakami K., Koura K., Sekine M., Shinozuka K., Miura K., and Hata T. J. Am. Soc. Chem. 106 (1984) 4552
13. Nelson B.P., Grimsrud T.E., Liles M.R., Goodman R.M., and Corn R.M. Anal. Chem. 73 (2001) 1
14. Palecek E., Fojta M., and Jelen F. Biochemistry 56 (2002) 85
15. Kurreck J., Wyszko E., Gillen C., and Erdmann V.A. Nucleic Acids Res. 30 (2002) 1911
16. Agrawal S. Biochim. Biophys. Acta 1489 (1999) 53
17. Ti G.S., Gaffney B.L., and Jones R.A. J. Am. Chem. Soc. 104 (1982) 1316
18. Fan Y., Gaffney B.L., and Jones R.A. Org. Lett. 6 (2004) 2555
19. Sinha N.D., Biernat J., and Koster H. Tetrahedron Lett. 24 (1983) 5843
20. Beaucage, S. L.; Bergstrom, D. E.; Glick, G. D.; Jones, R. A. John Wiley & Sons, Inc.: New York, 2000.
21. Vansdadia R.N., Roda K.P., and Parekh H. J. Inst. Chem. 61 (1989) 65
22. Heinicke G., Hung T.V., Prager R.H., and Ward A.D. Aust. J. Chem. 37 (1984) 831
23. Suzuki M., Nagasawa C., and Sugai T. Tetrahedron 57 (2001) 4841
24. Zhu Q., Delaney M.O., and Greenberg M.M. Bioorg. Med. Chem. Lett. 11 (2001) 1105
25. Allawi H.T., and SantaLucia Jr. J. Nucleic Acids Res. 26 (1998) 4925