A Four-Base Paired Genetic Helix with Expanded Size

Science

Volumn 302, Issue 5646, 2003, Pages 868-871

  Liu, Haibo ^a   Gao, Jianmin ^a   Lynch, Stephen R ^a   Saito, Y David ^a   Maynard, Lystranne ^a   Kool, Eric T ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; DNA; FLUORESCENCE; RNA; THERMODYNAMIC STABILITY;

GENETIC-PAIRING SYSTEMS;

GENES;

ADENINE; BENZENE; DNA; DNA BASE; RNA; THYMIDINE;

ARTICLE; BASE PAIRING; FLUORESCENCE; GENE STRUCTURE; MOLECULAR GENETICS; PRIORITY JOURNAL; THERMODYNAMICS;

ADENINE; BASE PAIRING; BASE SEQUENCE; BENZENE; CIRCULAR DICHROISM; HYDROGEN BONDING; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; NUCLEIC ACID CONFORMATION; NUCLEIC ACID DENATURATION; NUCLEIC ACID HYBRIDIZATION; OLIGODEOXYRIBONUCLEOTIDES; TEMPERATURE; THERMODYNAMICS; THYMINE;

EID: 0242332191     PISSN: 00368075     EISSN: None     Source Type: Journal    
DOI: 10.1126/science.1088334     Document Type: Article

References (28)

1. A. Murakami, K. R. Blake, P. S. Miller, Biochemistry 24, 4041 (1985).
2. M. Matsukura et al., Proc. Natl. Acad. Sci. U.S.A. 84 7706 (1987).
3. M. Egholm et al., Nature 365, 566 (1993).
4. A. Eschenmoser, Science 284, 2118 (1999).
5. A. A. Koshkin et al., Tetrahedron 54, 3607 (1998).
6. H. P. Rappaport, Nucleic Acids Res. 16, 7253 (1988).
7. S. A. Benner et al., Pure Appl. Chem. 70, 263 (1998).
8. T. J. Matray, E. T. Kool, J. Am. Chem. Soc. 120, 6191 (1998).
9. D. L. McMinn et al., J. Am. Chem. Soc. 121, 11585 (1999).
10. T. Mitsui et al., J. Am. Chem. Soc. 125, 5298 (2003).
11. K. Tanaka, A. Tengeiji, T. Kato, N. Toyama, M. Shionoya, Science 299, 1212 (2003).
12. R. A. Lessor, K. J. Gibson, N. J. Leonard, Biochemistry 23, 3868 (1984).
13. N. J. Leonard, M. A. Sprecker, A. G. Morrice, J. Am. Chem. Soc. 98, 3987 (1976).
14. J. Michel, J. J. Toulme, J. Vercauteren, S. Moreau, Nucleic Acids Res. 24, 1127 (1996).
15. M. Hoffer, Chem. Ber. 93, 2777 (1960).
16. Details of nucleoside phosphoramidite synthesis and characterization, of oligonucleotide synthesis, and of thermodynamics methods are given in the Supporting Online Material.
17. H. Liu, J. Gao, E. T. Kool, unpublished observations.
18. Hyperchromicity values of helices involving the expanded bases should not be directly compared with those of natural DNAs because the photophysical properties of xT and xA are different from those of T and A.
19. G. Prakash, E. T. Kool, J. Am. Chem. Soc. 114, 3523 (1992).
20. Thermal denaturation of the two single-stranded components alone under these conditions (5.0 μM in oligonucleotide) revealed transition temperatures of 26.5 and 27.5°C, significantly lower than that of the duplex.
21. F. Seela, A. Melenewski, C. Wei, Bioorg. Med. Chem. Lett. 17, 2173 (1997).
22. K. Groebke et al., Helv. Chim. Acta 81, 375 (1998).
23. M. F. H. Hoffmann, A. M. Brückner, T. Hupp, B. Engels, U. Diederichsen, Helv. Chim. Acta 83, 2580 (2000).
24. F. Seela, C. Wei, A. Melenewski, E. Feiling, Nucleosides Nucleotides 17, 2045 (1998).
25. H. Liu, J. Gao, L. Maynard, D. Saito, E. T. Kool, in preparation.
26. R. F. Kauffman, H. A. Lardy, J. R. Barrio, M. C. G. Barrio, N. J. Leonard, Biochemistry 17, 3686 (1978).
27. J. A. Piccirilli, T. Krauch, S. E. Moroney, S. A. Benner, Nature 343, 33 (1990).
28. We thank N. J. Leonard for helpful discussions. This work was supported by NIH grants GM63587 and GM52956. H. L. and J. G. acknowledge support from Stanford Graduate Fellowships.