Nucleosides and Nucleotides. 174. Synthesis of Oligodeoxynucleotides Containing 4′-C-[2-[[N-(2-Aminoethyl)carbamoyl]oxy]ethyl]thymidine and Their Thermal Stability and Nuclease-Resistance Properties

Journal of Organic Chemistry

Volumn 63, Issue 5, 1998, Pages 1660-1667

  Ueno, Yoshihito ^a   Nagasawa, Yuki ^a   Sugimoto, Isamu ^a   Kojima, Naoshi ^a   Kanazaki, Makiko ^a   Shuto, Satoshi ^a   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001191968     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9720492     Document Type: Article

References (46)

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24. Although several methods for introducing carbon substituents at the 4′-position of nucleosides have been reported, these methods are not stereoselective and the carbon substituents that can be introduced are limited: (a) Secrist, J. A., III; Winter, W. J., Jr. J. Am. Chem. Soc. 1978, 100, 2554-2556. (b) Youssefyeh, R. D.; Verheyden, P. H.; Moffat, J. G. J. Org. Chem. 1979, 44, 1301-1309. (c) Haraguchi, K.; Tanak, H.; Miyasaka, T. Tetrahedron Lett. 1990, 31, 227-230. (d) Haraguchi, K.; Tanak, H.; Itoh, Y.; Saito, S.; Miyasaka, T. Tetrahedron Lett. 1992, 33, 2841-2844. (e) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854-5855. (f) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1996, 61, 851-858. (g) Marx, A.; Erdmann, P.; Senn, M.; Korner, S.; Jungo, T.; Petretta, M.; Imwinkelried, P.; Dussy, A.; Kulicke, K. J.; Macko, L.; Zehnder, M.; Giese, B. Helv. Chim. Acta 1996, 79, 1980-1994. (h) Waga, T.; Ohrui, H.; Meguro, H. Nucleosides Nucleotides 1996, 15, 287-304. (i) O.-Yang, C.; Wu, H. Y.; Frase-Smith, W. B.; Walder, K. A. M. Tetrahedron Lett. 1992, 33, 37-40. (j) Bousquie, I.; Madiot, M.; Florent, J.-C.; Monneret, C. Bioorg. Med. Chem. Lett. 1996, 6, 1815-1818.
25. Although several methods for introducing carbon substituents at the 4′-position of nucleosides have been reported, these methods are not stereoselective and the carbon substituents that can be introduced are limited: (a) Secrist, J. A., III; Winter, W. J., Jr. J. Am. Chem. Soc. 1978, 100, 2554-2556. (b) Youssefyeh, R. D.; Verheyden, P. H.; Moffat, J. G. J. Org. Chem. 1979, 44, 1301-1309. (c) Haraguchi, K.; Tanak, H.; Miyasaka, T. Tetrahedron Lett. 1990, 31, 227-230. (d) Haraguchi, K.; Tanak, H.; Itoh, Y.; Saito, S.; Miyasaka, T. Tetrahedron Lett. 1992, 33, 2841-2844. (e) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854-5855. (f) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1996, 61, 851-858. (g) Marx, A.; Erdmann, P.; Senn, M.; Korner, S.; Jungo, T.; Petretta, M.; Imwinkelried, P.; Dussy, A.; Kulicke, K. J.; Macko, L.; Zehnder, M.; Giese, B. Helv. Chim. Acta 1996, 79, 1980-1994. (h) Waga, T.; Ohrui, H.; Meguro, H. Nucleosides Nucleotides 1996, 15, 287-304. (i) O.-Yang, C.; Wu, H. Y.; Frase-Smith, W. B.; Walder, K. A. M. Tetrahedron Lett. 1992, 33, 37-40. (j) Bousquie, I.; Madiot, M.; Florent, J.-C.; Monneret, C. Bioorg. Med. Chem. Lett. 1996, 6, 1815-1818.
26. Although several methods for introducing carbon substituents at the 4′-position of nucleosides have been reported, these methods are not stereoselective and the carbon substituents that can be introduced are limited: (a) Secrist, J. A., III; Winter, W. J., Jr. J. Am. Chem. Soc. 1978, 100, 2554-2556. (b) Youssefyeh, R. D.; Verheyden, P. H.; Moffat, J. G. J. Org. Chem. 1979, 44, 1301-1309. (c) Haraguchi, K.; Tanak, H.; Miyasaka, T. Tetrahedron Lett. 1990, 31, 227-230. (d) Haraguchi, K.; Tanak, H.; Itoh, Y.; Saito, S.; Miyasaka, T. Tetrahedron Lett. 1992, 33, 2841-2844. (e) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854-5855. (f) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1996, 61, 851-858. (g) Marx, A.; Erdmann, P.; Senn, M.; Korner, S.; Jungo, T.; Petretta, M.; Imwinkelried, P.; Dussy, A.; Kulicke, K. J.; Macko, L.; Zehnder, M.; Giese, B. Helv. Chim. Acta 1996, 79, 1980-1994. (h) Waga, T.; Ohrui, H.; Meguro, H. Nucleosides Nucleotides 1996, 15, 287-304. (i) O.-Yang, C.; Wu, H. Y.; Frase-Smith, W. B.; Walder, K. A. M. Tetrahedron Lett. 1992, 33, 37-40. (j) Bousquie, I.; Madiot, M.; Florent, J.-C.; Monneret, C. Bioorg. Med. Chem. Lett. 1996, 6, 1815-1818.
27. Although several methods for introducing carbon substituents at the 4′-position of nucleosides have been reported, these methods are not stereoselective and the carbon substituents that can be introduced are limited: (a) Secrist, J. A., III; Winter, W. J., Jr. J. Am. Chem. Soc. 1978, 100, 2554-2556. (b) Youssefyeh, R. D.; Verheyden, P. H.; Moffat, J. G. J. Org. Chem. 1979, 44, 1301-1309. (c) Haraguchi, K.; Tanak, H.; Miyasaka, T. Tetrahedron Lett. 1990, 31, 227-230. (d) Haraguchi, K.; Tanak, H.; Itoh, Y.; Saito, S.; Miyasaka, T. Tetrahedron Lett. 1992, 33, 2841-2844. (e) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854-5855. (f) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1996, 61, 851-858. (g) Marx, A.; Erdmann, P.; Senn, M.; Korner, S.; Jungo, T.; Petretta, M.; Imwinkelried, P.; Dussy, A.; Kulicke, K. J.; Macko, L.; Zehnder, M.; Giese, B. Helv. Chim. Acta 1996, 79, 1980-1994. (h) Waga, T.; Ohrui, H.; Meguro, H. Nucleosides Nucleotides 1996, 15, 287-304. (i) O.-Yang, C.; Wu, H. Y.; Frase-Smith, W. B.; Walder, K. A. M. Tetrahedron Lett. 1992, 33, 37-40. (j) Bousquie, I.; Madiot, M.; Florent, J.-C.; Monneret, C. Bioorg. Med. Chem. Lett. 1996, 6, 1815-1818.
28. Although several methods for introducing carbon substituents at the 4′-position of nucleosides have been reported, these methods are not stereoselective and the carbon substituents that can be introduced are limited: (a) Secrist, J. A., III; Winter, W. J., Jr. J. Am. Chem. Soc. 1978, 100, 2554-2556. (b) Youssefyeh, R. D.; Verheyden, P. H.; Moffat, J. G. J. Org. Chem. 1979, 44, 1301-1309. (c) Haraguchi, K.; Tanak, H.; Miyasaka, T. Tetrahedron Lett. 1990, 31, 227-230. (d) Haraguchi, K.; Tanak, H.; Itoh, Y.; Saito, S.; Miyasaka, T. Tetrahedron Lett. 1992, 33, 2841-2844. (e) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854-5855. (f) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1996, 61, 851-858. (g) Marx, A.; Erdmann, P.; Senn, M.; Korner, S.; Jungo, T.; Petretta, M.; Imwinkelried, P.; Dussy, A.; Kulicke, K. J.; Macko, L.; Zehnder, M.; Giese, B. Helv. Chim. Acta 1996, 79, 1980-1994. (h) Waga, T.; Ohrui, H.; Meguro, H. Nucleosides Nucleotides 1996, 15, 287-304. (i) O.-Yang, C.; Wu, H. Y.; Frase-Smith, W. B.; Walder, K. A. M. Tetrahedron Lett. 1992, 33, 37-40. (j) Bousquie, I.; Madiot, M.; Florent, J.-C.; Monneret, C. Bioorg. Med. Chem. Lett. 1996, 6, 1815-1818.
29. Although several methods for introducing carbon substituents at the 4′-position of nucleosides have been reported, these methods are not stereoselective and the carbon substituents that can be introduced are limited: (a) Secrist, J. A., III; Winter, W. J., Jr. J. Am. Chem. Soc. 1978, 100, 2554-2556. (b) Youssefyeh, R. D.; Verheyden, P. H.; Moffat, J. G. J. Org. Chem. 1979, 44, 1301-1309. (c) Haraguchi, K.; Tanak, H.; Miyasaka, T. Tetrahedron Lett. 1990, 31, 227-230. (d) Haraguchi, K.; Tanak, H.; Itoh, Y.; Saito, S.; Miyasaka, T. Tetrahedron Lett. 1992, 33, 2841-2844. (e) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854-5855. (f) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1996, 61, 851-858. (g) Marx, A.; Erdmann, P.; Senn, M.; Korner, S.; Jungo, T.; Petretta, M.; Imwinkelried, P.; Dussy, A.; Kulicke, K. J.; Macko, L.; Zehnder, M.; Giese, B. Helv. Chim. Acta 1996, 79, 1980-1994. (h) Waga, T.; Ohrui, H.; Meguro, H. Nucleosides Nucleotides 1996, 15, 287-304. (i) O.-Yang, C.; Wu, H. Y.; Frase-Smith, W. B.; Walder, K. A. M. Tetrahedron Lett. 1992, 33, 37-40. (j) Bousquie, I.; Madiot, M.; Florent, J.-C.; Monneret, C. Bioorg. Med. Chem. Lett. 1996, 6, 1815-1818.
30. Although several methods for introducing carbon substituents at the 4′-position of nucleosides have been reported, these methods are not stereoselective and the carbon substituents that can be introduced are limited: (a) Secrist, J. A., III; Winter, W. J., Jr. J. Am. Chem. Soc. 1978, 100, 2554-2556. (b) Youssefyeh, R. D.; Verheyden, P. H.; Moffat, J. G. J. Org. Chem. 1979, 44, 1301-1309. (c) Haraguchi, K.; Tanak, H.; Miyasaka, T. Tetrahedron Lett. 1990, 31, 227-230. (d) Haraguchi, K.; Tanak, H.; Itoh, Y.; Saito, S.; Miyasaka, T. Tetrahedron Lett. 1992, 33, 2841-2844. (e) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854-5855. (f) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1996, 61, 851-858. (g) Marx, A.; Erdmann, P.; Senn, M.; Korner, S.; Jungo, T.; Petretta, M.; Imwinkelried, P.; Dussy, A.; Kulicke, K. J.; Macko, L.; Zehnder, M.; Giese, B. Helv. Chim. Acta 1996, 79, 1980-1994. (h) Waga, T.; Ohrui, H.; Meguro, H. Nucleosides Nucleotides 1996, 15, 287-304. (i) O.-Yang, C.; Wu, H. Y.; Frase-Smith, W. B.; Walder, K. A. M. Tetrahedron Lett. 1992, 33, 37-40. (j) Bousquie, I.; Madiot, M.; Florent, J.-C.; Monneret, C. Bioorg. Med. Chem. Lett. 1996, 6, 1815-1818.
31. Although several methods for introducing carbon substituents at the 4′-position of nucleosides have been reported, these methods are not stereoselective and the carbon substituents that can be introduced are limited: (a) Secrist, J. A., III; Winter, W. J., Jr. J. Am. Chem. Soc. 1978, 100, 2554-2556. (b) Youssefyeh, R. D.; Verheyden, P. H.; Moffat, J. G. J. Org. Chem. 1979, 44, 1301-1309. (c) Haraguchi, K.; Tanak, H.; Miyasaka, T. Tetrahedron Lett. 1990, 31, 227-230. (d) Haraguchi, K.; Tanak, H.; Itoh, Y.; Saito, S.; Miyasaka, T. Tetrahedron Lett. 1992, 33, 2841-2844. (e) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854-5855. (f) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1996, 61, 851-858. (g) Marx, A.; Erdmann, P.; Senn, M.; Korner, S.; Jungo, T.; Petretta, M.; Imwinkelried, P.; Dussy, A.; Kulicke, K. J.; Macko, L.; Zehnder, M.; Giese, B. Helv. Chim. Acta 1996, 79, 1980-1994. (h) Waga, T.; Ohrui, H.; Meguro, H. Nucleosides Nucleotides 1996, 15, 287-304. (i) O.-Yang, C.; Wu, H. Y.; Frase-Smith, W. B.; Walder, K. A. M. Tetrahedron Lett. 1992, 33, 37-40. (j) Bousquie, I.; Madiot, M.; Florent, J.-C.; Monneret, C. Bioorg. Med. Chem. Lett. 1996, 6, 1815-1818.
32. Although several methods for introducing carbon substituents at the 4′-position of nucleosides have been reported, these methods are not stereoselective and the carbon substituents that can be introduced are limited: (a) Secrist, J. A., III; Winter, W. J., Jr. J. Am. Chem. Soc. 1978, 100, 2554-2556. (b) Youssefyeh, R. D.; Verheyden, P. H.; Moffat, J. G. J. Org. Chem. 1979, 44, 1301-1309. (c) Haraguchi, K.; Tanak, H.; Miyasaka, T. Tetrahedron Lett. 1990, 31, 227-230. (d) Haraguchi, K.; Tanak, H.; Itoh, Y.; Saito, S.; Miyasaka, T. Tetrahedron Lett. 1992, 33, 2841-2844. (e) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854-5855. (f) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1996, 61, 851-858. (g) Marx, A.; Erdmann, P.; Senn, M.; Korner, S.; Jungo, T.; Petretta, M.; Imwinkelried, P.; Dussy, A.; Kulicke, K. J.; Macko, L.; Zehnder, M.; Giese, B. Helv. Chim. Acta 1996, 79, 1980-1994. (h) Waga, T.; Ohrui, H.; Meguro, H. Nucleosides Nucleotides 1996, 15, 287-304. (i) O.-Yang, C.; Wu, H. Y.; Frase-Smith, W. B.; Walder, K. A. M. Tetrahedron Lett. 1992, 33, 37-40. (j) Bousquie, I.; Madiot, M.; Florent, J.-C.; Monneret, C. Bioorg. Med. Chem. Lett. 1996, 6, 1815-1818.
33. Although several methods for introducing carbon substituents at the 4′-position of nucleosides have been reported, these methods are not stereoselective and the carbon substituents that can be introduced are limited: (a) Secrist, J. A., III; Winter, W. J., Jr. J. Am. Chem. Soc. 1978, 100, 2554-2556. (b) Youssefyeh, R. D.; Verheyden, P. H.; Moffat, J. G. J. Org. Chem. 1979, 44, 1301-1309. (c) Haraguchi, K.; Tanak, H.; Miyasaka, T. Tetrahedron Lett. 1990, 31, 227-230. (d) Haraguchi, K.; Tanak, H.; Itoh, Y.; Saito, S.; Miyasaka, T. Tetrahedron Lett. 1992, 33, 2841-2844. (e) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854-5855. (f) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1996, 61, 851-858. (g) Marx, A.; Erdmann, P.; Senn, M.; Korner, S.; Jungo, T.; Petretta, M.; Imwinkelried, P.; Dussy, A.; Kulicke, K. J.; Macko, L.; Zehnder, M.; Giese, B. Helv. Chim. Acta 1996, 79, 1980-1994. (h) Waga, T.; Ohrui, H.; Meguro, H. Nucleosides Nucleotides 1996, 15, 287-304. (i) O.-Yang, C.; Wu, H. Y.; Frase-Smith, W. B.; Walder, K. A. M. Tetrahedron Lett. 1992, 33, 37-40. (j) Bousquie, I.; Madiot, M.; Florent, J.-C.; Monneret, C. Bioorg. Med. Chem. Lett. 1996, 6, 1815-1818.
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