The conformationally constrained N-methanocarba-dT analogue adopts an unexpected C4′-exo sugar pucker in the structure of a DNA hairpin

Biochemistry

Volumn 51, Issue 13, 2012, Pages 2639-2641

  Pallan, Pradeep S ^a   Marquez, Victor E ^b   Egli, Martin ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DNA HAIRPIN; FURANOSE; SUGAR PUCKER;

HEXANE; SCAFFOLDS;

SUGARS;

DNA B; NORTH METHANOCARBA 2 DEOXYTHYMIDINE; UNCLASSIFIED DRUG;

ARTICLE; CONCEPTUAL FRAMEWORK; CRYSTALLIZATION; DNA HAIRPIN; ENZYME CONFORMATION; NONHUMAN; PRIORITY JOURNAL;

CARBOHYDRATES; DNA; MODELS, MOLECULAR; NUCLEIC ACID CONFORMATION;

EID: 84859394741     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi300215k     Document Type: Article

References (35)

1. Marquez, V. E. (2008) in Modified Nucleosides in Biochemistry, Biotechnology and Medicine (Herdewijn, P., Ed.) pp 307-341, Wiley-VCH, Weinheim, Germany.
2. Mathé, C. and Périgaud, C. (2008) Eur. J. Org. Chem. 1489-1505
3. Crooke, S. T. (2007) in Antisense Drug Technology: Principles, Strategies, and Applications, 2nd ed., CRC Press, Boca Raton, FL.
4. Bennett, C. F. and Swayze, E. E. (2010) Annu. Rev. Pharmacol. Toxicol. 50, 259-293
5. Rakesh, N. and Wengel, J. (2010) Chem. Biodiversity 7, 536-542
6. Herdewijn, P. (2010) Chem. Biodiversity 7, 1-59
7. Leumann, C. J. (2005) Chimia 59, 776-779
8. Trujillo, C. A., Nery, A. A., Alves, J. M., Martins, A. H., and Ulrich, H. (2007) Clin. Ophthalmol. 1, 393-402
9. Manoharan, M. (1999) Biochim. Biophys. Acta 1489, 117-130
10. Manoharan, M., Akinc, A., Pandey, R. K., Qin, J., Hadwiger, P., John, M., Mills, K., Charisse, K., Maier, M. A., Nechev, L., Greene, E. M., Pallan, P. S., Rozners, E., Rajeev, K. G., and Egli, M. (2011) Angew. Chem., Int. Ed. 50, 2284-2288
11. Wengel, J. (1999) Acc. Chem. Res. 32, 301-310
12. Tereshko, V., Gryaznov, S., and Egli, M. (1998) J. Am. Chem. Soc. 120, 269-283
13. Gryaznov, S. (2010) Chem. Biodiversity 9, 477-493
14. Prakash, T. P. (2011) Chem. Biodiversity 8, 1616-1641
15. Egli, M. and Pallan, P. S. (2010) Chem. Biodiversity 7, 60-89
16. Pallan, P. S., Greene, E., Jicman, P., Pandey, R., Manoharan, M., Rozners, E., and Egli, M. (2011) Nucleic Acids Res. 39, 3482-3495
17. Kaur, H., Wengel, J., and Maiti, S. (2008) Biochemistry 47, 1218-1227
18. Altona, C. and Sundaralingam, M. (1972) J. Am. Chem. Soc. 94, 8205-8212
19. Ezzitouni, A. and Marquez, V. E. (1997) J. Chem. Soc., Perkin Trans. 1, 1073-1078
20. Marquez, V. E., Ben-Kasus, T., Barchi, J. J., Jr., Green, K. M., Nicklaus, M. C., and Agbaria, R. (2004) J. Am. Chem. Soc. 126, 543-549
21. Boyer, P. L., Julias, J. G., Marquez, V. E., and Hughes, S. H. (2005) J. Mol. Biol. 345, 441-450
22. Eoff., R. L., McGrath, C. E., Maddukuri, L., Salamanca-Pinzón, S. G., Marquez, V. E., Marnett, L. J., Guengerich, F. P., and Egli, M. (2010) Angew. Chem., Int. Ed. 49, 7481-7485
23. Maier, M. A., Choi, Y., Gaus, H., Barchi, J. J., Jr., Marquez, V. E., and Manoharan, M. (2004) Nucleic Acids Res. 32, 3642-3650
24. Wu, Z., Maderia, M., Barchi, J. J., Jr., Marquez, V. E., and Bax, A. (2005) Proc. Natl. Acad. Sci. U.S.A. 102, 24-28
25. Maderia, M., Shenoy, S., Van, Q. N., Marquez, V. E., and Barchi, J. J., Jr. (2007) Nucleic Acids Res. 35, 1978-1991
26. Macias, A. T., Banavali, N. K., and MacKerell, A. D., Jr. (2007) Biopolymers 85, 438-449
27. Gessner, R. V., Quigley, G. J., and Egli, M. (1994) J. Mol. Biol. 236, 1154-1168
28. Sun, G., Voigt, J. H., Marquez, V. E., and Nicklaus, M. C. (2005) Nucleosides, Nucleotides Nucleic Acids 24, 1029-1032
29. Goodsell, D. S. (2010) Nat. Educ. 3, 39
30. Vanegas, P. L., Hudson, G. A., Davis, A. R., Kelly, S. C., Kirkpatrick, C. C., and Znosko, B. M. (2012) Nucleic Acids Res. 40, 439-444
31. Chattopadhyaya, R., Ikuta, S., Grzeskowiak, K., and Dickerson, R. E. (1988) Nature 334, 175-179
32. Holbrook, S. R., Cheong, C., Tinoco, I., Jr., and Kim, S. H. (1991) Nature 353, 579-581
33. Egli, M., Tereshko, V., Murshudov, G. N., Sanishvili, R., Liu, X., and Lewis, F. D. (2003) J. Am. Chem. Soc. 125, 10842-10849
34. Pallan, P. S., Prakash, T. P., Li, F., Eoff, R. L., Manoharan, M., and Egli, M. (2009) Chem. Commun., 15, 2017-2019
35. Martín-Pintado, N., Yahyaee Anzahaeeb, M., Campos, R., Damha, M. J., and González, C. (2011) 94th Canadian Chemistry Conference, June 5-9.