Synthesis of light-responsive bridged nucleic acid and changes in affinity with complementary ssRNA

ChemBioChem

Volumn 10, Issue 11, 2009, Pages 1784-1788

  Morihiro, Kunihiko ^a   Kodama, Tetsuya ^a   Nishida, Masaru ^a   Imanishi, Takeshi ^a   Obika, Satoshi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Antisense agents; BNA; Nucleic acids; Photoirradiation; RNA

Indexed keywords

COMPLEMENTARY RNA; NUCLEIC ACID; NUCLEOPHILE; OLIGONUCLEOTIDE; SINGLE STRANDED RNA;

ARTICLE; BINDING AFFINITY; NUCLEIC ACID SYNTHESIS; PRIORITY JOURNAL; PROTEIN MODIFICATION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; RNA BINDING; RNA PURIFICATION; ULTRAVIOLET RADIATION;

ACETALS; BASE SEQUENCE; LIGHT; NUCLEIC ACIDS; OLIGONUCLEOTIDES; RNA; TRANSITION TEMPERATURE;

EID: 70349557920     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200900241     Document Type: Article

References (35)

1. a) D. Tuncel, M. Katterle, Chem. Eur. J. 2008, 14, 4110-4116
2. b) T. Yamamoto, H. C. Chen, E. Guigard, C. M. Kay, R. O. Ryan, Biochemistry 2008, 47, 11647-11652.
3. a) R. Tashiro, H. Sugiyama, J. Am. Chem. Soc. 2005, 127, 2094-2097
4. b) Y. Shiraishi, R. Miyamoto, T. Hirai, Tetrahedron Lett. 2007, 48, 6660-6664.
5. a) Q. Li, V. W. Yam, Angew. Chem. 2007, 119, 3556-3559
6. Q. Li, V. W. Yam, Angew. Chem. Int. Ed. 2007, 46, 3486-3489
7. b) K. A. Marvin, R. L. Kerby, H. Youn, G. P. Roberts, J. N. Burstyn, Biochemistry 2008, 47, 9016-9028.
8. H. Asanuma, T. Ito, T. Yoshida, X. Liang, M. Komiyama, Angew. Chem. 1999, 111, 2547-2549
9. H. Asanuma, T. Ito, T. Yoshida, X. Liang, M. Komiyama, Angew. Chem. Int. Ed. 1999, 38, 2393-2395.
10. a) G. Mayer, A. Heckel, Angew. Chem. 2006, 118, 5020-5042
11. G. Mayer, A. Heckel, Angew. Chem. Int. Ed. 2006, 45, 4900-4921
12. b) D. D. Young, A. Deiters, Org. Biomol. Chem. 2007, 5, 999-1005
13. c) G. C. R. Ellis-Davies, Nat. Methods 2007, 4, 619-628.
14. a) D. D. Young, H. Lusic, M. O. Lively, J. A. Yoder, A. Deiters, ChemBioChem 2008, 9, 2937-2940
15. b) S. Shah, S. Rangarajan, S. H. Friedman, Angew. Chem. 2005, 117, 1352-1356
16. S. Shah, S. Rangarajan, S. H. Friedman, Angew. Chem. Int. Ed. 2005, 44, 1328-1332
17. c) A. Heckel, G. Mayer, J. Am. Chem. Soc. 2005, 127, 822-823.
18. a) Y. Hari, S. Obika, R. Ohnishi, K. Eguchi, T. Osaki, H. Ohishi, T. Imanishi, Bioorg. Med. Chem. 2006, 14, 1029-1038
19. b) Y. Mitsuoka, T. Kodama, R. Ohnishi, Y. Hari, T. Imanishi, S. Obika, Nucleic Acids Res. 2009, 37, 1225-1238
20. c) M. Kuwahara, S. Obika, J. Nagashima, Y. Ohta, Y. Suto, H. Ozaki, H. Sawai, T. Imanishi, Nucleic Acids Res. 2008, 36, 4257-4265.
21. a) S. K. Singh, P. Nielsen, A. A. Koshkin, J. Wengel, Chem. Commun. 1998, 455-456
22. b) S. Obika, D. Nanbu, Y. Hari, K. Morio, Y. In, T. Ishida, T. Imanishi, Tetrahedron Lett. 1997, 38, 8735-8738
23. c) S. Obika, D. Nanbu, Y. Hari, J. Andoh, K. Morio, T. Doi, T. Imanishi, Tetrahedron Lett. 1998, 39, 5401-5404.
24. a) C. Altona, M. Sundaralingam, J. Am. Chem. Soc. 1972, 94, 8205-8212
25. b) S. Arnott, D. W. L. Hukins, S. D. Dover, Biochem. Biophys. Res. Commun. 1972, 48, 1392-1399.
26. a) U. Zehavi, B. Amit, A. Patchornik, J. Org. Chem. 1972, 37, 2281-2285
27. b) Z. Y. Zhang, B. D. Smith, Bioconjugate Chem. 1999, 10, 1150-1152
28. c) M. Endo, K. Nakayama, T. Majima, J. Org. Chem. 2004, 69, 4292-4298.
29. T. Wu, K. Nauwelaerts, A. van Aerschot, M. Froeyen, E. Lescrinier, P. Herdewijn, J. Org. Chem. 2006, 71, 5423-5431.
30. K. D. Nielsen, F. Kirpekar, P. Roepstorff, J. Wengel, Bioorg. Med. Chem. 1995, 3, 1493-1502.
31. R. D. Youssefyeh, J. P. H. Verheyden, J. G. Moffatt, J. Org. Chem. 1979, 44, 1301-1309.
32. NOESY spectrum of compound 4 showed no correlation between acetal-H and 1′-H and strong correlation between acetal-H, 1″-H and TIPDS-H; this data strongly supports the indicated configuration. It should be impossible to show such a NOESY spectrum for the other diastereomer.
33. 1H COSY NMR experiments, which showed that the photoproduct has two secondary hydroxyl groups (2′-OH and 3′-OH) and a benzoyl substituent at the 4′-C-hydroxymethyl group. See Supporting Information, S14.
34. a) H. G. Song, C. Moon, M. H. Park, J. I. Moon, C. Moon, J. Health Sci. 2008, 54, 464-470
35. b) A. Yoshida, H. Takemura, H. Inoue, T. Miyashita, T. Ueda, Cancer Res. 2006, 66, 5772-5780.