Synthesis of N,N-dialkylaniline-2'-deoxyuridine conjugates for DNA- mediated electron transfer studies

Nucleosides, Nucleotides and Nucleic Acids

Volumn 19, Issue 5-6, 2000, Pages 851-866

  Kerr, Charles E ^a   Eaton, Bruce E ^b   Netzel, Thomas L ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

^b WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 [2 (4 N,N DIMETHYLAMINOPHENYL)ETHYL)] 2' DEOXYURIDINE; 5 [3 (N METHYLPHENYLAMINO)PROPANOYL] 2' DEOXYURIDINE; ANILINE DERIVATIVE; DEOXYURIDINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; ELECTRON TRANSPORT; LIGAND BINDING; SPECTROSCOPY;

EID: 0034130867     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1080/15257770008033027     Document Type: Article

References (70)

1. Netzel, T. L. A Comparison of Theoretical and Experimental Studies of Electron Transfer Within DNA Duplexes in Organic and Inorganic Photochemistry; Ramamurthy, V. and Schanze, K. S., eds.; Marcel Dekker, Inc.: New York, 1998; Molecular and Supramolecular Photochemistry Series, 2, 1-54.
2. Netzel, T. L. A Comparison of Theoretical and Experimental Studies of Electron Transfer Within DNA Duplexes in Organic and Inorganic Photochemistry; Ramamurthy, V. and Schanze, K. S., eds.; Marcel Dekker, Inc.: New York, 1998; Molecular and Supramolecular Photochemistry Series, 2, 1-54.
3. Barbara, P. F.; Olson, E. J. J. Adv. Chem. Phys. 1999, 107, 647-676.
4. Barton, J. K. Pure Appl. Chem. 1998, 70, 873-879.
5. Giese, B.; Wessely, S.; Spormann, M.; Lindemann, U.; Meggers, E.; Michel-Beyerle, M. E. Angew. Chem., Int. Ed. Engl. 1999, 38, 996-997.
6. Meggers, E.; Michel-Beyerle, M. E.; Giese, B. J. Am. Chem. Soc. 1998, 120, 12950-12955.
7. Harriman, A. Angew. Chem., Int. Ed. Engl. 1999, 38, 945-949.
8. Fukui, K.; Tanaka, K. Angew. Chem., Int. Ed. Engl. 1998, 37, 158-161.
9. Lewis, F. D.; Wu, T.; Zhang, Y.; Letsinger, R. L.; Greenfield, S. R.; Wasielewski, M. R. Science 1997, 277, 673-676.
10. Ratner, M. Nature 1999, 397, 480-481.
11. Jortner, J.; Bixon, M.; Langenbacher, T.; Michel-Beyerle, M. E. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12759-12765.
12. Wilson, E. K. Chemical and Engineering News 1999, August 23, 43-48.
13. Lewis, F. D.; Liu, X.; Miller, S. E.; Wasielewski, M. R. J. Am. Chem. Soc. 1999, 121, 9746-9747.
14. Kelley, S. O.; Holmlin, R. E.; Stemp, E. D. A.; Barton, J. K. J. Am. Chem. Soc. 1997, 119, 9861-9870.
15. Kelley, S. O.; Jackson, N. M.; Hill, M. G.; Barton, J. K. Angew. Chem., Int. Ed. Engl. 1999, 38, 941-944.
16. Kelley, S. O.; Barton, J. K. Science 1999, 283, 375-381.
17. Wan, C.; Fiebig, T.; Kelley, S. O.; Treadway, C. R.; Barton, J. K.; Zewail, A. H. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 6014-6019.
18. Kelley, S. O.; Barton, J. K. Chem. Biol. 1998, 5, 413-425.
19. Stemp, E. D. A.; Arkin, M. R.; Barton, J. K. J. Amer. Chem. Soc. 1997, 119, 2921-2925.
20. Dandliker, P. J.; Holmlin, R. E.; Barton, J. K. Science 1997, 275, 1465-1468.
21. Dandliker, P. J.; Holmlin, R. E.; Barton, J. K. FASEB J. 1996, 10, 1659-1659.
22. Ly, D.; Sanii, L.; Schuster, G. B. J. Am. Chem. Soc. 1999, 121, 9400-9410.
23. Melvin, T.; Plumb, M. A.; Botchway, S. W.; O'Neill, P. O.; Parter, A. W. Photochem. Photobiol. 1995, 61, 584-591.
24. Netzel, T. L. "NSF Progress Report, Aug. '98 - July '99" U. S. National Science Foundation, 1999, CHE-9709318.
25. Netzel, T. L.; Nafisi, K.; Headrick, J.; Eaton, B. E. J. Phys. Chem. 1995, 99, 17948-17955.
26. Netzel, T. L.; Zhao, M.; Nafisi, K.; Headrick, J.; Sigman, M. S.; Eaton, B. E. J. Am. Chem. Soc. 1995, 117, 9119-9128.
27. Kerr, C. E.; Michell, C. D.; Ying, Y.-M.; Eaton, B. E.; Netzel, T. L. J. Phys. Chem. B 2000, 104, (in press).
28. Kerr, C. E.; Mitchell, C. D.; Headrick, J.; Eaton, B. E.; Netzel, T. L. J. Phys. Chem. B 2000, 104, (in press).
29. 2Br). Shida, T. Electronic Absorption Spectra of Radical Ions; Elsevier: New York, 1988, p 208.
30. th ACS National Meeting: New Orleans, 1996.
31. Crouch, G. Modified Uridine Nucleosides and DNA: New Concepts in Antiviral and Antineoplastic Therapy; Ph.D. Thesis, Washington State University: Pullman, 1996, WSU C5 1996 C7, pp 130.
32. Crouch, G. J.; Eaton, B. E. Nucleosides & Nucleotides 1994, 13, 939-944.
33. Mitchell, C. D.; Netzel, T. L. J. Phys. Chem. B 1999, 103, (in press).
34. Robins, M. J.; Vinayak, R. S.; Wood, S. G. Tetrahedron Lett. 1990, 31, 3731-3734.
35. Hobbs, F. W. J. Org. Chem. 1989, 54, 3420-3422.
36. Robins, M. J.; Barr, P. J. J. Org. Chem. 1983, 48, 1854-1862.
37. Robins, M. J.; Barr, P. J. Tetrahedron Lett. 1981, 22, 421-424.
38. Cruickshank, K. A.; Stockwell, D. L. Tetrahedron Lett. 1988, 29, 5221-5224.
39. Kerr, C. E. Allenic Iron Carbonyls, Nucleoside Analogs, and Enzymology of Oligonucleotide Preparations Using Nucleoside Analogs; Ph. D. Thesis, Washington State University: Pullman, 1997, WSU C5 1997 K42, pp 112.
40. Tolstikov, G. A.; Mustafin, A. G.; Gataullin, R. R.; Spirikhin, L. V.; Abdrakhmanov, I. B. Bull. Russ. Acad. Sci Div. Chem. Sci. (Engl. Transl.) 1992, 41, 1135.
41. Tolstikov, G. A.; Mustafin, A. G.; Gataullin, R. R.; Spirikhin, L. V.; Sultanova, V. S.; Abdrakhmanov, I. B. Russian Chemistry Bulletin 1993, 42, 563-566.
42. Korshun, V. A.; Manasova, E. V.; Balakin, K. V.; Prokhorenko, I. A.; Buchatskii, A. G.; Berlin, Y. A. Rus. J. Bioorg. Chem. 1996, 22, 807-809.
43. Korshun, V. A.; Manasova, E. V.; Balakin, K. V.; Malakhov, A. D.; Perepelov, A. V.; Sokolova, T. A.; Berlin, Y. A. Nucleosides & Nucleotides 1998, 17, 1809-1812.
44. Hurley, D. J.; Tor, Y. J. Am. Chem. Soc. 1998, 120, 2194-2195.
45. Khan, S. I.; Beilstein, A. E.; Grinstaff, M. W. Inorg. Chem. 1999, 38, 418-419.
46. Khan, S. I.; Grinstaff, M. W. J. Am. Chem. Soc. 1999, 121, 4704-4705.
47. Kahl, J. D.; Greenberg, M. M. J. Am. Chem. Soc. 1999, 121, 597-604.
48. Gibson, K. J.; Benkovic, S. J. Nuc. Acids Res. 1987, 15, 6455-6467.
49. Graham, D.; Parkinson, J. A.; Brown, T. J. Chem. Soc., Perkin Trans. 1998, 1131-1138.
50. Haralambidis, J.; Chai, M.; Tregear, G. W. Nuc. Acids Res. 1987, 15, 4857-4876.
51. Latham, J. A.; Johnson, R.; Toole, J. J. Nuc. Acids Res. 1994, 22, 2817-2822.
52. Shealy, Y. F.; O'Dell, C. A.; Arnett, G.; Shannon, W. H. J. Med. Chem. 1986, 29, 79-84.
53. Henrianna, P.; Schram, K. H.; Smith, D. L.; Gupta, S. P.; Townsend, L. B.; McCloskey, J. A. J. Org. Chem. 1982, 47, 3923-3932.
54. Lawson, A. M.; Stillwell, R. N.; Tacker, M. M.; Tsuboyama, K.; McCloskey, J. A. J. Am. Chem. Soc. 1971, 93, 1014-1023.
55. Al-Razzak, L. A.; Schwepler, D.; Decedue, C. J.; Balzarini, J.; De Clercq, E.; Mertes, M. P. J. Med. Chem. 1987, 30, 409-419.
56. Wigerinck, P.; Pannecoque, C.; Snoeck, R.; Claes, P.; De Clercq, E.; Heredwijn, P. J. Med. Chem. 1991, 34, 2383-2389.
57. Bigge, C. F.; Mertes, M. P. J. Org. Chem. 1981, 46, 1994-1997.
58. Hassan, M. E. Recl. Trav. Chim. Pays-Bas 1986, 105, 30-32.
59. Pein, C.-D.; Cech, D. Tetrahedron Lett. 1985, 26, 4915-4918.
60. Pein, C.-D.; Cech, D. Z Chem. 1985, 25, 328-329.
61. Reefschlaeger, J.; Pein, C.-D.; Cech, D. J. Med. Chem. 1988, 31, 393-397.
62. While it would appear helpful to use DMT-protected nucleosides throughout the synthesis of 2, the hydrogenation conditions necessary to reduce the alkyne linkage would remove the DMT group.
63. Coulson, D. R. Inorg. Syn. 1972, 13, 121-124.
64. EDMA was prepared by adaptation of the literature procedure for synthesis of ethynylferrocene: Wurst, K.; Elsner, O.; Schottenberger, H. Synlett 1995, 833-834.
65. 13C resonances were observed instead of the expected 27, possibly the result of diastereotopic arrangement of subgroups within the DMT group.
66. Alternately, flash chromatography performed by loading crude material in neat chloroform followed by elution with 17% EtOAc in chloroform may be used to isolate 14.
67. 6 instead of the expected 16. The septet produced by the solvent is probably obscuring one resonance, while another is likely coincident with some other analyte resonance. Unfortunately solubility severely limits the number of NMR solvents that can be used to study this nucleoside.
68. 2.
69. 13C resonances were observed instead of the expected 26, possibly the result of diastereotopic arrangement of subgroups within the DMT group.
70. The reported mass is the average of three separate measurements with the following values: 677.3279, 677.3312, 677.2961.