A versatile modification of on-column oligodeoxynucleotides using a copper-catalyzed oxidative acetylenic coupling reaction

Journal of the American Chemical Society

Volumn 125, Issue 38, 2003, Pages 11545-11552

  Minakawa, Noriaki ^a   Ono, Yayoi ^a   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COUPLING REACTION;

CATALYSIS; CHEMICAL MODIFICATION; COPPER; MOLECULES;

ORGANIC COMPOUNDS;

ACETYLENE; ANTHRAQUINONE; BIOTIN; COPPER; FLUORESCEIN; FUNCTIONAL GROUP; METHYLAMINE; OLIGODEOXYNUCLEOTIDE; RESIN;

ARTICLE; ASSAY; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; DNA FLANKING REGION; OXIDATION; SYNTHESIS;

ACETYLENE; ANTHRAQUINONES; BIOTIN; CATALYSIS; COPPER; FLUORESCEIN; OLIGONUCLEOTIDES; OXIDATION-REDUCTION;

EID: 0141869063     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036055t     Document Type: Article

References (58)

1. (a) Uhlmann, E.; Peyman, A. Chem. Rev. 1990, 90, 543-584.
2. (b) Crooke, S. T., Lebleu, B., Eds. Antisense Research and Application; CRC Press: Boca Raton, FL, 1993.
3. (a) Smith, L. M.; Sanders, J. Z.; Kaiser, R. J.; Hughes, P.; Dodd, C.; Connell, C. R.; Heiner, C.; Kent, S. B. H.; Hood, L. E. Nature 1986, 321, 674-679.
4. (b) Chehab, F. F.; Kan, Y. W. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 9178-9182.
5. (c) Ju, J.; Ruan, C.; Fuller, C. W.; Glazer, A. N.; Mathies, R. A. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 4347-4351.
6. Erlich, H. A.; Gelfand, D.; Sninsky, J. J. Science 1991, 252, 1643-1650.
7. (a) Zhang, P.; Beck, T.; Tan, W. Angew. Chem., Int. Ed. 2001, 40, 402-405.
8. (b) Kuhn, H.; Demidov, V. V.; Coull, J. M.; Fiandaca, M. J.; Gildea, B. D.; Frank-Kamenetskii, M. D. J. Am. Chem. Soc. 2002, 124, 1097-1102.
9. (c) Summerer, D.; Marx, A. Angew. Chem., Int. Ed. 2002, 41, 3620-3622.
10. (a) Fodor, S. P. A.; Read, J. L.; Pirrung, M. C.; Stryer, L.; Lu, A T.; Solas, D. Science 1991, 251, 767-773.
11. (b) Schena, M.; Shalon, D.; Davis, R. W.; Brown, P. O. Science 1995, 270, 467-470.
12. Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 1925-1963.
13. Goodchild, J. Bioconjugate Chem. 1990, 1, 165-187.
14. For examples: (a) Chehab, F. F.; Kan, Y. W. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 9178-9182.
15. (b) Randolph, J. B.; Waggoner, A. S. Nucleic Acids Res. 1997, 25, 2923-2929.
16. (c) Smith, L. M.; Fung, S.; Hunkapiller, M. W.; Hunkapiller, T. J.; Hood, L. E. Nucleic Acids Res. 1985, 13, 2399-2412.
17. (d) Jenkins, Y.; Barton, J. K. J. Am. Chem. Soc. 1992, 114, 8736-8738.
18. (e) Sigurdsson, S. T.; Eckstein, F. Nucleic Acids Res. 1996, 24, 3129-3133.
19. Except for ref 8, various postsynthetic modifications of ODN were reported. For examples: (a) Connolly, B. A. Nucleic Acids Res. 1985, 13, 4485-4502.
20. (b) Jones, D. S.; Barstad, P. A.; Feild, M. J.; Hachmann, J. P.; Hayag, M. S.; Hill, K. W.; Iverson, G. M.; Livingston, D. A.; Palanki, M. S.; Tibbetts, A. R.; Yu, L.; Coutts, S. M. J. Med. Chem. 1995, 38, 2138-2144.
21. (c) Rajur, S. B.; Roth, C. M.; Morgan, J. R.; Yarmush, M. L. Bioconjugate Chem. 1997, 8, 935-940.
22. (d) Zuckermann, R.; Corey, D.; Schultz, P. Nucleic Acids Res. 1987, 15, 5305-5320.
23. (e) Hanna, M. M.; Meyer, K. L. Bioconjugate Chem. 1996, 7, 401-412.
24. (f) Coleman, R. S.; Arthur, J. C.; McCary, J. L. Tetrahedron 1997, 53, 11191-11202.
25. (g) Ono, A.; Haginoya, N.; Kiyokawa, M.; Minakawa, N.; Matsuda, A. Bioorg. Med. Chem. Lett. 1994, 4, 361-366.
26. (h) Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconjugate Chem. 1997, 8, 271-280.
27. (i) Nomura, Y.; Ueno, Y.; Matsuda, A. Nucleic Acids Res. 1997, 25, 2784-2791.
28. (j) MacMillan, A. M.; Verdine, G. L. J. Org. Chem. 1990, 55, 5931-5933.
29. (k) Xu, Y.-Z.; Zheng, Q.; Swann, P. Tetrahedron 1992, 48, 1729-1740.
30. (l) Gao, H.; Fathi, R.; Gaffney, B. L.; Goswami, B.; Kung, P.-P.; Rhee, Y.; Jin, R.; Jones, R. A. J. Org. Chem. 1992, 57, 5931-5933.
31. (m) Kim, S. J.; Stone, M. P.; Harris, C. M.; Harris, T. M. J. Am. Chem. Soc. 1992, 114, 5480-5481.
32. (a) Kahl, J. D.; Greenberg, M. M. J. Am. Chem. Soc. 1999, 121, 597-604.
33. (b) Hwang, J.-T.; Greenberg, M. M. Org. Lett. 1999, 1, 2021-2024.
34. (c) Hwang, J.-T.; Greenberg, M. M. J. Org. Chem. 2001, 66, 363-369.
35. (a) Khan, S. I.; Grinstaff, M. W. J. Am. Chem. Soc. 1999, 121, 4704-4705.
36. (b) Beilstein, A. E.; Grinstaff, M. W. Chem. Commun. 2000, 509-510.
37. For examples: (a) Hill, K. W.; Taunton-Rigby, J.; Carter, J. D.; Kropp, E.; Vagle, K.; Pieken, W.; McGee, D. P. C.; Husar, G. M.; Leuck, M.; Anziano, D. J.; Sebesta, D. P. J. Org. Chem. 2001, 66, 5352-5358.
38. (b) Graham, D.; Grondin, A.; Mchugh, C.; Fruk, L.; Smith, W. E. Tetrahedron Lett. 2002, 43, 4785-4788.
39. (c) Okamoto, A.; Taiji, T.; Tainaka, K.; Saito, I. Bioorg. Med. Chem. Lett. 2002, 12, 1895-1896.
40. (d) Seo, T. S.; Li, Z.; Ruparel, H.; Ju, J. J. Org. Chem. 2003, 68, 609-612.
41. For a review, see: Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39. 2632-2657.
42. Crisp, G. T.; Flynn, B. L. J. Org. Chem. 1993. 58, 6614-6619.
43. Graham, D.; Parkinson, J. A.; Brown, T. J. Chem. Soc., Perkin Trans. 1 1998, 1131-1138.
44. Hurley, D. J.; Tor, Y. J. Am. Chem. Soc. 2002, 124, 3749-3762.
45. When the reaction was carried out in the absence of 15, ODN3 was obtained in approximately 20% yield, which was analyzed by MALDI-TOF/MASS measurement.
46. ODNI-9 possess DMTr groups on their 5′-termini, except when the ODNs are used for MALDI-TOF/MASS measurements and primer extension assays.
47. (a) Brown, T.; Pritchard, C. E.; Turner, G.; Salisbury, S. A. J. Chem. Soc., Chem. Commun. 1989, 891-893.
48. (b) Weiler, J.; Hoheisel, J. D. Anal. Biochem. 1990, 189, 218-227.
49. In the original paper by Brown et al., FMOC-sarcosine was used.
50. When 7 was subjected to the acetylenic coupling reaction under the same conditions, the product of cleavage of the succinyl linker was detected in approximately 20% yield.
51. Although we did not prepare a hexamer on CPG500 analogous to 27 (possessing a methylamino-modified linker), our preliminary attempt using a hexamer on CPG500 possessing a succinyl linker did not give the coupling product when the EdU unit was introduced at the internal 3′-end.
52. Bellon, L.; Wincott, F. In Solid-Phase Synthesis. A Practical Guide; Kates, S. A., Albericio, F., Eds.; Marcel Dekker Inc.: New York, 2000; pp 475-528 and references therein.
53. Resins and Reagent Catalog, Technical Handbook; Argonaut Technologies, Inc.; pp 144-148.
54. (a) De Napoli, L.; Galeone, A.; Mayol, L.; Messere, A.; Piccialli, G.; Santacroce, C. J. Chem. Soc., Perkin Trans. 1 1993, 747-749.
55. (b) De Napoli, L.; Galeone, A.; Mayol, L.; Messere, A.; Montesarchio, D. ; Piccialli, G. Bioorg. Med. Chem. 1995, 3, 1325-1329.
56. Forns, P.; Fields, G. B. In Solid-Phase Synthesis. A Practical Guide; Kates, S. A., Albericio, F., Eds.; Marcel Dekker Inc.: New York, 2000; pp 1-77 and references therein.
57. The synthesis of 29a-c was presented in the Supporting Information.
58. Gisin, B. F. Anal. Chim. Acta 1972, 58, 248-249.