Soft metal-mediated base pairing with novel synthetic nucleosides possessing an O,S-donor ligand

Journal of Organic Chemistry

Volumn 73, Issue 16, 2008, Pages 6092-6098

  Takezawa, Yusuke ^a   Tanaka, Kentaro ^b   Yori, Maiko ^a   Tashiro, Shohei ^a   Shiro, Motoo ^c   Shionoya, Mitsuhiko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

^c RIGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BASE PAIRINGS; BASE PAIRS; BUILDING BLOCKS; CHEMICAL EQUATIONS; DNA DUPLEXES; DONOR LIGANDS; METAL INCORPORATION; NUCLEOBASE; SITE-SELECTIVE; TRANSITION METAL IONS;

CHEMICAL REACTIONS; LIGANDS; METAL IONS; NUCLEIC ACIDS; NUCLEOTIDES; ORGANIC ACIDS; PALLADIUM; TRANSITION METAL COMPOUNDS; TRANSITION METALS;

METALS;

DOUBLE STRANDED DNA; LEAD; LIGAND; MERCAPTOPYRIDONE; METAL; NUCLEIC ACID BASE; NUCLEOSIDE; PLATINUM; PYRIDONE DERIVATIVE; PYRITHIONE; TRANSITION ELEMENT;

ARTICLE; BASE PAIRING; HYDROPHOBICITY; SYNTHESIS;

DNA; LIGANDS; MODELS, MOLECULAR; NICKEL; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; NUCLEIC ACID CONFORMATION; NUCLEOSIDES; ORGANOMETALLIC COMPOUNDS; ORGANOPLATINUM COMPOUNDS; PALLADIUM; PLATINUM; PYRIDINES; PYRIDONES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 50149091746     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800587d     Document Type: Article

References (57)

1. (a) Henry, A. A.; Romesberg, F. E. Curr. Opin. Chem. Biol. 2003, 7, 727-733.
2. (b) Hirao, I. Curr. Opin. Chem. Biol. 2006, 10, 622-627, and references therein.
3. For example: (a) Bergstorm, D. E. In Current Protocols in Nucleic Acid Chemistry; Beaucage, S. L., Bergstorm, D. E., Glick, G. D., Jones, R. A. Eds.; Wiley: New York, 2001; Unit 1.4.
4. (b) Kool, E. T. Acc. Chem. Res. 2002, 35, 936-943.
5. (c) Okamoto, A. Bull. Chem. Soc. Jpn. 2005, 78, 2083-2097.
6. For example: (a) Switzer, C.; Moroney, S. E.; Benner, S. A. J. Am. Chem. Soc. 1989, 111, 8322-8323.
7. (b) Piccirilli, J. A.; Krauch, T.; Moroney, S. E.; Benner, S. A. Nature 1990, 343, 33-37.
8. (c) Sismour, A. M.; Benner, S. A. Nucleic Acids Res. 2005, 33, 5640-5646.
9. For example: (a) Schweitzer, B. A.; Kool, E. T. J. Am. Chem. Soc. 1995, 117, 1863-1872.
10. (b) Leconte, A. M.; Chen, L.; Romesberg, F. E. J. Am. Chem. Soc. 2005, 127, 12470-12471.
11. (c) Hirao, I.; Kimoto, M.; Mitsui, T.; Fujiwara, T.; Kawai, R.; Sato, A.; Harada, Y.; Yokoyama, S. Nat. Methods 2006, 3, 729-735.
12. (d) Hirao, I.; Mitsui, T.; Kimoto, M.; Yokoyama, S. J. Am. Chem. Soc. 2007, 129, 15549-15555.
13. (a) Shionoya, M.; Tanaka, K. Curr. Opin. Chem. Biol. 2004, 8, 592-597.
14. (b) Tanaka, K.; Shionoya, M. Chem. Lett. 2006, 35, 695-699.
15. (c) Tanaka, K.; Shionoya, M. Coord. Chem. Rev. 2007, 251, 2732-2742.
16. (d) Clever, G. H.; Kaul, C.; Carell, T. Angew. Chem., Int. Ed. 2007, 46, 6226-6236.
17. Tanaka, K.; Shionoya, M. J. Org. Chem. 1999, 64, 5002-5003.
18. (a) Cao, H.; Tanaka, K.; Shionoya, M. Chem. Pharm. Bull. 2000, 48, 1745-1748.
19. (b) Tanaka, K.; Tasaka, M.; Cao, H.; Shionoya, M. Eur. J. Pharm. Sci 2001, 13, 77-83.
20. (c) Tasaka, M.; Tanaka, K.; Shiro, M.; Shionoya, M. Supramol. Chem. 2001, 13, 671-675.
21. (d) Tanaka, K.; Tasaka, M.; Cao, H.; Shionoya, M. Supramol. Chem. 2002, 14, 255-261.
22. (e) Shionoya, M.; Tanaka, K. Bull. Chem. Soc. Jpn. 2000, 73, 1945-1954.
23. Tanaka, K.; Yamada, Y.; Shionoya, M. J. Am. Chem. Soc. 2002, 124, 8802-8803.
24. Tanaka, K.; Tengeiji, A.; Kato, T.; Toyama, N.; Shiro, M.; Shionoya, M. J. Am. Chem. Soc. 2002, 124, 12494-12498.
25. Müller, J.; Böhme, D.; Lax, P.; Cerda, M. M.; Roitzsch, M. Chem. - Eur. J. 2005, 11, 6246-6253.
26. (a) Weizman, H.; Tor, Y. J. Am. Chem. Soc. 2001, 123, 3375-3376.
27. (b) Zhang, L.; Meggers, E. J. Am. Chem. Soc. 2005, 127, 74-75.
28. (c) Switzer, C.; Sinha, S.; Kim, P. H.; Heuberger, B. D. Angew. Chem., Int. Ed. 2005, 44, 1529-1532.
29. (d) Switzer, C.; Shin, D. Chem. Commun. 2005, 1342-1344.
30. (a) Meggers, E.; Holland, P. L.; Tolman, W. B.; Romesberg, F. E.; Schultz, P. G. J. Am. Chem. Soc. 2000, 122, 10714-10715.
31. (b) Atwell, S.; Meggers, E.; Spraggon, G.; Schultz, P. G. J. Am. Chem. Soc. 2001, 123, 12364-12367.
32. (c) Zimmermann, N.; Meggers, E.; Schultz, P. G. Bioorg. Chem. 2004, 32, 13-25.
33. (d) Shin, D.; Switzer, C. Chem. Commun. 2007, 4401-4403.
34. (e) Heuberger, B. D.; Shin, D.; Switzer, C. Org. Lett. 2008, 10, 1091-1094.
35. Zimmermann, N.; Meggers, E.; Schultz, P. G. J. Am. Chem. Soc. 2002, 124, 13684-13685.
36. (a) Clever, G. H.; Polborn, K.; Carell, T. Angew. Chem., Int. Ed. 2005, 44, 7204-7208.
37. (b) Clever, G. H.; Söltl, Y.; Burks, H.; Spahl, W.; Carell, T. Chem. - Eur. J. 2006, 12, 8708-8718.
38. (c) Clever, G. H.; Carell, T. Angew. Chem., Int. Ed. 2007, 46, 250-253.
39. (a) Brotschi, C.; Leumann, C. J. Nucleosides Nucleotides Nucleic Acids 2003, 22, 1195-1197.
40. (b) Polonius, F.-A.; Müller, J. Angew. Chem., Int. Ed. 2007, 46, 5602-5604.
41. Tanaka, K.; Tengeiji, A.; Kato, T.; Toyama, N.; Shionoya, M. Science 2003, 299, 1212-1213.
42. (a) Tanaka, K.; Clever, G. H.; Takezawa, Y.; Yamada, Y.; Kaul, C.; Shionoya, M.; Carell, T. Nat. Nanotech. 2006, 1, 190-194.
43. See also: (b) Müller, J. Nature 2006, 444, 698.
44. 2+-T metallo-base pair. See: (a) Kukleynik, Z.; Marzilli, L. G. Inorg. Chem. 1996, 35, 5654-5662.
45. (b) Miyake, Y.; Togashi, H.; Tashiro, M.; Yamaguchi, H.; Oda, S.; Kudo, M.; Tanaka, Y.; Kondo, Y.; Sawa, R.; Fujimoto, T.; Machinami, T.; Ono, A. J. Am. Chem. Soc. 2006, 128, 2172-2173.
46. Okada, T.; Tanaka, K.; Shiro, M.; Shionoya, M. Chem. Commun. 2005, 1484-1486.
47. Katoh, A.; Tsukahara, T.; Saito, R.; Ghosh, K. K.; Yoshikawa, Y.; Kojima, Y.; Tamura, A.; Sakurai, H. Chem. Lett. 2002, 31, 114-115.
48. (a) Lewis, J. A.; Cohen, S. M. Inorg. Chem. 2004, 43, 6534-6536.
49. (b) Monga, V.; Patrick, B. O.; Orvig, C. Inorg. Chem. 2005, 44, 2666-2677.
50. (c) Monga, V.; Thompson, K. H.; Yuen, V. G.; Sharma, V.; Patrick, B. O.; McNeill, J. H.; Orvig, C. Inorg. Chem. 2005, 44, 2678-2688.
51. (a) Lewis, J. A.; Puerta, D. T.; Cohen, S. M. Inorg. Chem. 2003, 42, 7455-7459.
52. (b) Lewis, J. A.; Tran, B. L.; Puerta, D. T.; Rumberger, E. M.; Hendrickson, D. N.; Cohen, S. M. Dalton Trans. 2005, 2588-2596.
53. Trécourt, F.; Mallet, M.; Mengin, O.; Gervais, B.; Quéguiner, G. Tetrahedron 1993, 49, 8373-8380.
54. Lister, T.; Prager, R. H.; Tsaconas, M.; Wilkinson, K. L. Aust. J. Chem. 2003, 56, 913-916.
55. This compound was prepared according to an improved procedure in which acetyl chloride was used as an HCl generator. See: (a) Rolland, V.; Kotera, M.; Lhomme, J. Synth. Commun. 1997, 27, 3505-3511.
56. Dash, B.; Dora, E. K.; Panda, C. S. Heterocycles 1982, 19, 2093-2098.
57. -1 for the carbonyl group of hydroxypyridone (Figure S3, Supporting Information).