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Volumn 125, Issue 33, 2003, Pages 9970-9982

New base pairing motifs. The synthesis and thermal stability of oligodeoxynucleotides containing imidazopyridopyrimidine nucleosides with the ability to form four hydrogen bonds

Author keywords

[No Author keywords available]

Indexed keywords

INTRAMOLECULAR CYCLIZATIONS;

EID: 0043022290     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0347686     Document Type: Article
Times cited : (108)

References (83)
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    • For examples except for antisense and antigene methodologies: (a) Goeddel, D. V.; Yansura, D. G.; Caruthers, M. H. Proc. Natl. Acad. Sci. U.S.A. 1978. 75, 3578-3582. (b) Taboury, J. A.; Adam, S.; Taillandier, E.; Neumann, J.-M.; Tran-Dinh, S.; Huynh-Dinh, T.; Langlois d'Estaintot, B.; Conti, M.; Igolen, J. Nucleic Acids Res. 1984, 12, 6291-6305. (c) Chollet, A.; Kawashima, E. Nucleic Acids Res. 1988, 16, 305-317. (d) Solomon, M. S.; Hopkins, P. B. J. Org. Chem. 1993, 58, 2232-2243. (e) Langouet, S.; Muller, M.; Guengerich, F. P. Biochemistry 1997, 36, 6069-6079. (f) Beaussire, J.-J.; Pochet, S. Tetrahedron 1998, 54, 13547-13556. (g) Yang, X.; Sugiyama, H.; Ikeda, S.; Saito, I.; Wang, A. H.-J. Biophys. J. 1998, 75, 1163-1171. (h) He, X.; Krawczyk, S. H.; Swaminathan, S.; Shea, R. G.; Dougherty, J. P.; Terhorst, T.; Law, V. S.; Griffin. L. C.; Coutre, S.; Bischofberger, N. J. Med. Chem. 1998, 41, 2234-2242. (i) Sherer, E. C.; Harris, S. A.; Soliva, R.; Orozco, M.; Laughton, C. A. J. Am. Chem. Soc. 1999, 121, 5981-5991. (j) Wang, Z.; Rizzo, C. J. Org. Lett. 2000, 2, 227-230. (k) Sugiyama, T.; Schweinberger, E.; Kazimierczuk, Z.; Ranmzaeva, N.; Rosemeyer, H.; Seela, F. Chem. Eur. J. 2000, 6, 369-378. (l) Sessler, J. L. ; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 39, 1300-1303. (m) Seela, F.; Debelak, H. Nucleic Acids Res. 2000, 28, 3224-3232. (n) Wilhelmsson, L. M.; Holmen, A.; Lincoln, P.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 2001, 123, 2434-2435. (l) Sessler, J. L.; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 39, 1300-1303. (m) Seela, F.; Debelak, H. Nucleic Acids Res. 2000, 28, 3224-3232. (n) Wilhelmsson, L. M.; Holmen, A.; Lincoln, P.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 2001, 123, 2434-2435.
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    • 0031660471 scopus 로고    scopus 로고
    • For examples except for antisense and antigene methodologies: (a) Goeddel, D. V.; Yansura, D. G.; Caruthers, M. H. Proc. Natl. Acad. Sci. U.S.A. 1978. 75, 3578-3582. (b) Taboury, J. A.; Adam, S.; Taillandier, E.; Neumann, J.-M.; Tran-Dinh, S.; Huynh-Dinh, T.; Langlois d'Estaintot, B.; Conti, M.; Igolen, J. Nucleic Acids Res. 1984, 12, 6291-6305. (c) Chollet, A.; Kawashima, E. Nucleic Acids Res. 1988, 16, 305-317. (d) Solomon, M. S.; Hopkins, P. B. J. Org. Chem. 1993, 58, 2232-2243. (e) Langouet, S.; Muller, M.; Guengerich, F. P. Biochemistry 1997, 36, 6069-6079. (f) Beaussire, J.-J.; Pochet, S. Tetrahedron 1998, 54, 13547-13556. (g) Yang, X.; Sugiyama, H.; Ikeda, S.; Saito, I.; Wang, A. H.-J. Biophys. J. 1998, 75, 1163-1171. (h) He, X.; Krawczyk, S. H.; Swaminathan, S.; Shea, R. G.; Dougherty, J. P.; Terhorst, T.; Law, V. S.; Griffin. L. C.; Coutre, S.; Bischofberger, N. J. Med. Chem. 1998, 41, 2234-2242. (i) Sherer, E. C.; Harris, S. A.; Soliva, R.; Orozco, M.; Laughton, C. A. J. Am. Chem. Soc. 1999, 121, 5981-5991. (j) Wang, Z.; Rizzo, C. J. Org. Lett. 2000, 2, 227-230. (k) Sugiyama, T.; Schweinberger, E.; Kazimierczuk, Z.; Ranmzaeva, N.; Rosemeyer, H.; Seela, F. Chem. Eur. J. 2000, 6, 369-378. (l) Sessler, J. L. ; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 39, 1300-1303. (m) Seela, F.; Debelak, H. Nucleic Acids Res. 2000, 28, 3224-3232. (n) Wilhelmsson, L. M.; Holmen, A.; Lincoln, P.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 2001, 123, 2434-2435. (l) Sessler, J. L.; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 39, 1300-1303. (m) Seela, F.; Debelak, H. Nucleic Acids Res. 2000, 28, 3224-3232. (n) Wilhelmsson, L. M.; Holmen, A.; Lincoln, P.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 2001, 123, 2434-2435.
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    • Yang, X.1    Sugiyama, H.2    Ikeda, S.3    Saito, I.4    Wang, A.H.-J.5
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    • For examples except for antisense and antigene methodologi (a) Goeddel, D. V.; Yansura, D. G.; Caruthers, M. H. Proc. Natl. Acad. Sci. U.S.A. 1978. 75, 3578-3582. (b) Taboury, J. A.; Adam, S.; Taillandier, E.; Neumann, J.-M.; Tran-Dinh, S.; Huynh-Dinh, T.; Langlois d'Estaintot, B.; Conti, M.; Igolen, J. Nucleic Acids Res. 1984, 12, 6291-6305. (c) Chollet, A.; Kawashima, E. Nucleic Acids Res. 1988, 16, 305-317. (d) Solomon, M. S.; Hopkins, P. B. J. Org. Chem. 1993, 58, 2232-2243. (e) Langouet, S.; Muller, M.; Guengerich, F. P. Biochemistry 1997, 36, 6069-6079. (f) Beaussire, J.-J.; Pochet, S. Tetrahedron 1998, 54, 13547-13556. (g) Yang, X.; Sugiyama, H.; Ikeda, S.; Saito, I.; Wang, A. H.-J. Biophys. J. 1998, 75, 1163-1171. (h) He, X.; Krawczyk, S. H.; Swaminathan, S.; Shea, R. G.; Dougherty, J. P.; Terhorst, T.; Law, V. S.; Griffin. L. C.; Coutre, S.; Bischofberger, N. J. Med. Chem. 1998, 41, 2234-2242. (i) Sherer, E. C.; Harris, S. A.; Soliva, R.; Orozco, M.; Laughton, C. A. J. Am. Chem. Soc. 1999, 121, 5981-5991. (j) Wang, Z.; Rizzo, C. J. Org. Lett. 2000, 2, 227-230. (k) Sugiyama, T.; Schweinberger, E.; Kazimierczuk, Z.; Ranmzaeva, N.; Rosemeyer, H.; Seela, F. Chem. Eur. J. 2000, 6, 369-378. (l) Sessler, J. L. ; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 39, 1300-1303. (m) Seela, F.; Debelak, H. Nucleic Acids Res. 2000, 28, 3224-3232. (n) Wilhelmsson, L. M.; Holmen, A.; Lincoln, P.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 2001, 123, 2434-2435. (l) Sessler, J. L.; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 39, 1300-1303. (m) Seela, F.; Debelak, H. Nucleic Acids Res. 2000, 28, 3224-3232. (n) Wilhelmsson, L. M.; Holmen, A.; Lincoln, P.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 2001, 123, 2434-2435.
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    • For examples except for antisense and antigene methodologies: (a) Goeddel, D. V.; Yansura, D. G.; Caruthers, M. H. Proc. Natl. Acad. Sci. U.S.A. 1978. 75, 3578-3582. (b) Taboury, J. A.; Adam, S.; Taillandier, E.; Neumann, J.-M.; Tran-Dinh, S.; Huynh-Dinh, T.; Langlois d'Estaintot, B.; Conti, M.; Igolen, J. Nucleic Acids Res. 1984, 12, 6291-6305. (c) Chollet, A.; Kawashima, E. Nucleic Acids Res. 1988, 16, 305-317. (d) Solomon, M. S.; Hopkins, P. B. J. Org. Chem. 1993, 58, 2232-2243. (e) Langouet, S.; Muller, M.; Guengerich, F. P. Biochemistry 1997, 36, 6069-6079. (f) Beaussire, J.-J.; Pochet, S. Tetrahedron 1998, 54, 13547-13556. (g) Yang, X.; Sugiyama, H.; Ikeda, S.; Saito, I.; Wang, A. H.-J. Biophys. J. 1998, 75, 1163-1171. (h) He, X.; Krawczyk, S. H.; Swaminathan, S.; Shea, R. G.; Dougherty, J. P.; Terhorst, T.; Law, V. S.; Griffin. L. C.; Coutre, S.; Bischofberger, N. J. Med. Chem. 1998, 41, 2234-2242. (i) Sherer, E. C.; Harris, S. A.; Soliva, R.; Orozco, M.; Laughton, C. A. J. Am. Chem. Soc. 1999, 121, 5981-5991. (j) Wang, Z.; Rizzo, C. J. Org. Lett. 2000, 2, 227-230. (k) Sugiyama, T.; Schweinberger, E.; Kazimierczuk, Z.; Ranmzaeva, N.; Rosemeyer, H.; Seela, F. Chem. Eur. J. 2000, 6, 369-378. (l) Sessler, J. L. ; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 39, 1300-1303. (m) Seela, F.; Debelak, H. Nucleic Acids Res. 2000, 28, 3224-3232. (n) Wilhelmsson, L. M.; Holmen, A.; Lincoln, P.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 2001, 123, 2434-2435. (l) Sessler, J. L.; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 39, 1300-1303. (m) Seela, F.; Debelak, H. Nucleic Acids Res. 2000, 28, 3224-3232. (n) Wilhelmsson, L. M.; Holmen, A.; Lincoln, P.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 2001, 123, 2434-2435.
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    • Sherer, E.C.1    Harris, S.A.2    Soliva, R.3    Orozco, M.4    Laughton, C.A.5
  • 14
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    • For examples except for antisense and antigene methodologies: (a) Goeddel, D. V.; Yansura, D. G.; Caruthers, M. H. Proc. Natl. Acad. Sci. U.S.A. 1978. 75, 3578-3582. (b) Taboury, J. A.; Adam, S.; Taillandier, E.; Neumann, J.-M.; Tran-Dinh, S.; Huynh-Dinh, T.; Langlois d'Estaintot, B.; Conti, M.; Igolen, J. Nucleic Acids Res. 1984, 12, 6291-6305. (c) Chollet, A.; Kawashima, E. Nucleic Acids Res. 1988, 16, 305-317. (d) Solomon, M. S.; Hopkins, P. B. J. Org. Chem. 1993, 58, 2232-2243. (e) Langouet, S.; Muller, M.; Guengerich, F. P. Biochemistry 1997, 36, 6069-6079. (f) Beaussire, J.-J.; Pochet, S. Tetrahedron 1998, 54, 13547-13556. (g) Yang, X.; Sugiyama, H.; Ikeda, S.; Saito, I.; Wang, A. H.-J. Biophys. J. 1998, 75, 1163-1171. (h) He, X.; Krawczyk, S. H.; Swaminathan, S.; Shea, R. G.; Dougherty, J. P.; Terhorst, T.; Law, V. S.; Griffin. L. C.; Coutre, S.; Bischofberger, N. J. Med. Chem. 1998, 41, 2234-2242. (i) Sherer, E. C.; Harris, S. A.; Soliva, R.; Orozco, M.; Laughton, C. A. J. Am. Chem. Soc. 1999, 121, 5981-5991. (j) Wang, Z.; Rizzo, C. J. Org. Lett. 2000, 2, 227-230. (k) Sugiyama, T.; Schweinberger, E.; Kazimierczuk, Z.; Ranmzaeva, N.; Rosemeyer, H.; Seela, F. Chem. Eur. J. 2000, 6, 369-378. (l) Sessler, J. L. ; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 39, 1300-1303. (m) Seela, F.; Debelak, H. Nucleic Acids Res. 2000, 28, 3224-3232. (n) Wilhelmsson, L. M.; Holmen, A.; Lincoln, P.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 2001, 123, 2434-2435. (l) Sessler, J. L.; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 39, 1300-1303. (m) Seela, F.; Debelak, H. Nucleic Acids Res. 2000, 28, 3224-3232. (n) Wilhelmsson, L. M.; Holmen, A.; Lincoln, P.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 2001, 123, 2434-2435.
    • (2000) Org. Lett. , vol.2 , pp. 227-230
    • Wang, Z.1    Rizzo, C.J.2
  • 15
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    • For examples except for antisense and antigene methodologies: (a) Goeddel, D. V.; Yansura, D. G.; Caruthers, M. H. Proc. Natl. Acad. Sci. U.S.A. 1978. 75, 3578-3582. (b) Taboury, J. A.; Adam, S.; Taillandier, E.; Neumann, J.-M.; Tran-Dinh, S.; Huynh-Dinh, T.; Langlois d'Estaintot, B.; Conti, M.; Igolen, J. Nucleic Acids Res. 1984, 12, 6291-6305. (c) Chollet, A.; Kawashima, E. Nucleic Acids Res. 1988, 16, 305-317. (d) Solomon, M. S.; Hopkins, P. B. J. Org. Chem. 1993, 58, 2232-2243. (e) Langouet, S.; Muller, M.; Guengerich, F. P. Biochemistry 1997, 36, 6069-6079. (f) Beaussire, J.-J.; Pochet, S. Tetrahedron 1998, 54, 13547-13556. (g) Yang, X.; Sugiyama, H.; Ikeda, S.; Saito, I.; Wang, A. H.-J. Biophys. J. 1998, 75, 1163-1171. (h) He, X.; Krawczyk, S. H.; Swaminathan, S.; Shea, R. G.; Dougherty, J. P.; Terhorst, T.; Law, V. S.; Griffin. L. C.; Coutre, S.; Bischofberger, N. J. Med. Chem. 1998, 41, 2234-2242. (i) Sherer, E. C.; Harris, S. A.; Soliva, R.; Orozco, M.; Laughton, C. A. J. Am. Chem. Soc. 1999, 121, 5981-5991. (j) Wang, Z.; Rizzo, C. J. Org. Lett. 2000, 2, 227-230. (k) Sugiyama, T.; Schweinberger, E.; Kazimierczuk, Z.; Ranmzaeva, N.; Rosemeyer, H.; Seela, F. Chem. Eur. J. 2000, 6, 369-378. (l) Sessler, J. L. ; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 39, 1300-1303. (m) Seela, F.; Debelak, H. Nucleic Acids Res. 2000, 28, 3224-3232. (n) Wilhelmsson, L. M.; Holmen, A.; Lincoln, P.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 2001, 123, 2434-2435. (l) Sessler, J. L.; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 39, 1300-1303. (m) Seela, F.; Debelak, H. Nucleic Acids Res. 2000, 28, 3224-3232. (n) Wilhelmsson, L. M.; Holmen, A.; Lincoln, P.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 2001, 123, 2434-2435.
    • (2000) Chem. Eur. J. , vol.6 , pp. 369-378
    • Sugiyama, T.1    Schweinberger, E.2    Kazimierczuk, Z.3    Ranmzaeva, N.4    Rosemeyer, H.5    Seela, F.6
  • 16
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    • For examples except for antisense and antigene methodologies: (a) Goeddel, D. V.; Yansura, D. G.; Caruthers, M. H. Proc. Natl. Acad. Sci. U.S.A. 1978. 75, 3578-3582. (b) Taboury, J. A.; Adam, S.; Taillandier, E.; Neumann, J.-M.; Tran-Dinh, S.; Huynh-Dinh, T.; Langlois d'Estaintot, B.; Conti, M.; Igolen, J. Nucleic Acids Res. 1984, 12, 6291-6305. (c) Chollet, A.; Kawashima, E. Nucleic Acids Res. 1988, 16, 305-317. (d) Solomon, M. S.; Hopkins, P. B. J. Org. Chem. 1993, 58, 2232-2243. (e) Langouet, S.; Muller, M.; Guengerich, F. P. Biochemistry 1997, 36, 6069-6079. (f) Beaussire, J.-J.; Pochet, S. Tetrahedron 1998, 54, 13547-13556. (g) Yang, X.; Sugiyama, H.; Ikeda, S.; Saito, I.; Wang, A. H.-J. Biophys. J. 1998, 75, 1163-1171. (h) He, X.; Krawczyk, S. H.; Swaminathan, S.; Shea, R. G.; Dougherty, J. P.; Terhorst, T.; Law, V. S.; Griffin. L. C.; Coutre, S.; Bischofberger, N. J. Med. Chem. 1998, 41, 2234-2242. (i) Sherer, E. C.; Harris, S. A.; Soliva, R.; Orozco, M.; Laughton, C. A. J. Am. Chem. Soc. 1999, 121, 5981-5991. (j) Wang, Z.; Rizzo, C. J. Org. Lett. 2000, 2, 227-230. (k) Sugiyama, T.; Schweinberger, E.; Kazimierczuk, Z.; Ranmzaeva, N.; Rosemeyer, H.; Seela, F. Chem. Eur. J. 2000, 6, 369-378. (l) Sessler, J. L. ; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 39, 1300-1303. (m) Seela, F.; Debelak, H. Nucleic Acids Res. 2000, 28, 3224-3232. (n) Wilhelmsson, L. M.; Holmen, A.; Lincoln, P.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 2001, 123, 2434-2435. (l) Sessler, J. L.; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 39, 1300-1303. (m) Seela, F.; Debelak, H. Nucleic Acids Res. 2000, 28, 3224-3232. (n) Wilhelmsson, L. M.; Holmen, A.; Lincoln, P.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 2001, 123, 2434-2435.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 1300-1303
    • Sessler, J.L.1    Sathiosatham, M.2    Doerr, K.3    Lynch, V.4    Abboud, K.A.5
  • 17
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    • For examples except for antisense and antigene methodologies: (a) Goeddel, D. V.; Yansura, D. G.; Caruthers, M. H. Proc. Natl. Acad. Sci. U.S.A. 1978. 75, 3578-3582. (b) Taboury, J. A.; Adam, S.; Taillandier, E.; Neumann, J.-M.; Tran-Dinh, S.; Huynh-Dinh, T.; Langlois d'Estaintot, B.; Conti, M.; Igolen, J. Nucleic Acids Res. 1984, 12, 6291-6305. (c) Chollet, A.; Kawashima, E. Nucleic Acids Res. 1988, 16, 305-317. (d) Solomon, M. S.; Hopkins, P. B. J. Org. Chem. 1993, 58, 2232-2243. (e) Langouet, S.; Muller, M.; Guengerich, F. P. Biochemistry 1997, 36, 6069-6079. (f) Beaussire, J.-J.; Pochet, S. Tetrahedron 1998, 54, 13547-13556. (g) Yang, X.; Sugiyama, H.; Ikeda, S.; Saito, I.; Wang, A. H.-J. Biophys. J. 1998, 75, 1163-1171. (h) He, X.; Krawczyk, S. H.; Swaminathan, S.; Shea, R. G.; Dougherty, J. P.; Terhorst, T.; Law, V. S.; Griffin. L. C.; Coutre, S.; Bischofberger, N. J. Med. Chem. 1998, 41, 2234-2242. (i) Sherer, E. C.; Harris, S. A.; Soliva, R.; Orozco, M.; Laughton, C. A. J. Am. Chem. Soc. 1999, 121, 5981-5991. (j) Wang, Z.; Rizzo, C. J. Org. Lett. 2000, 2, 227-230. (k) Sugiyama, T.; Schweinberger, E.; Kazimierczuk, Z.; Ranmzaeva, N.; Rosemeyer, H.; Seela, F. Chem. Eur. J. 2000, 6, 369-378. (l) Sessler, J. L. ; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 39, 1300-1303. (m) Seela, F.; Debelak, H. Nucleic Acids Res. 2000, 28, 3224-3232. (n) Wilhelmsson, L. M.; Holmen, A.; Lincoln, P.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 2001, 123, 2434-2435. (l) Sessler, J. L.; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 39, 1300-1303. (m) Seela, F.; Debelak, H. Nucleic Acids Res. 2000, 28, 3224-3232. (n) Wilhelmsson, L. M.; Holmen, A.; Lincoln, P.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 2001, 123, 2434-2435.
    • (2000) Nucleic Acids Res. , vol.28 , pp. 3224-3232
    • Seela, F.1    Debelak, H.2
  • 18
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    • For examples except for antisense and antigene methodologies: (a) Goeddel, D. V.; Yansura, D. G.; Caruthers, M. H. Proc. Natl. Acad. Sci. U.S.A. 1978. 75, 3578-3582. (b) Taboury, J. A.; Adam, S.; Taillandier, E.; Neumann, J.-M.; Tran-Dinh, S.; Huynh-Dinh, T.; Langlois d'Estaintot, B.; Conti, M.; Igolen, J. Nucleic Acids Res. 1984, 12, 6291-6305. (c) Chollet, A.; Kawashima, E. Nucleic Acids Res. 1988, 16, 305-317. (d) Solomon, M. S.; Hopkins, P. B. J. Org. Chem. 1993, 58, 2232-2243. (e) Langouet, S.; Muller, M.; Guengerich, F. P. Biochemistry 1997, 36, 6069-6079. (f) Beaussire, J.-J.; Pochet, S. Tetrahedron 1998, 54, 13547-13556. (g) Yang, X.; Sugiyama, H.; Ikeda, S.; Saito, I.; Wang, A. H.-J. Biophys. J. 1998, 75, 1163-1171. (h) He, X.; Krawczyk, S. H.; Swaminathan, S.; Shea, R. G.; Dougherty, J. P.; Terhorst, T.; Law, V. S.; Griffin. L. C.; Coutre, S.; Bischofberger, N. J. Med. Chem. 1998, 41, 2234-2242. (i) Sherer, E. C.; Harris, S. A.; Soliva, R.; Orozco, M.; Laughton, C. A. J. Am. Chem. Soc. 1999, 121, 5981-5991. (j) Wang, Z.; Rizzo, C. J. Org. Lett. 2000, 2, 227-230. (k) Sugiyama, T.; Schweinberger, E.; Kazimierczuk, Z.; Ranmzaeva, N.; Rosemeyer, H.; Seela, F. Chem. Eur. J. 2000, 6, 369-378. (l) Sessler, J. L. ; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 39, 1300-1303. (m) Seela, F.; Debelak, H. Nucleic Acids Res. 2000, 28, 3224-3232. (n) Wilhelmsson, L. M.; Holmen, A.; Lincoln, P.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 2001, 123, 2434-2435. (l) Sessler, J. L.; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 39, 1300-1303. (m) Seela, F.; Debelak, H. Nucleic Acids Res. 2000, 28, 3224-3232. (n) Wilhelmsson, L. M.; Holmen, A.; Lincoln, P.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 2001, 123, 2434-2435.
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    • note
    • N, respectively.
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    • note
    • 2,4-Diaminopyrimidine and 2,4-dimethoxypyrimidine were also examined as starting materials to prepare the tributylstannylpyrimidine derivatives. In the former case, introduction of the tributylstannyl group did not work well, while in the latter, it was very difficult to carry out the intramolecular cyclization to give the desired tricyclic skeletons after the Stille coupling reaction.
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    • Additional references for the synthesis of 5-8: (a) Minakawa, N.; Takeda, T.; Sasaki, T.; Matsuda, A.; Ueda, T. J. Med. Chem. 1991, 34, 778-786. (b) Harris, M. G.; Stewart, R. Can. J. Chem. 1977, 55, 3800-3806. (c) Das, B.; Kundu, N. G. Synthetic Commun. 1988, 18, 855-867.
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    • Additional references for the synthesis of 5-8: (a) Minakawa, N.; Takeda, T.; Sasaki, T.; Matsuda, A.; Ueda, T. J. Med. Chem. 1991, 34, 778-786. (b) Harris, M. G.; Stewart, R. Can. J. Chem. 1977, 55, 3800-3806. (c) Das, B.; Kundu, N. G. Synthetic Commun. 1988, 18, 855-867.
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    • Additional references for the synthesis of 5-8: (a) Minakawa, N.; Takeda, T.; Sasaki, T.; Matsuda, A.; Ueda, T. J. Med. Chem. 1991, 34, 778-786. (b) Harris, M. G.; Stewart, R. Can. J. Chem. 1977, 55, 3800-3806. (c) Das, B.; Kundu, N. G. Synthetic Commun. 1988, 18, 855-867.
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    • Das, B.1    Kundu, N.G.2
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    • note
    • The maximal absorption of 5 was observed at 237 nm, while those of 7 were observed at 244 and 280 nm. respectively.
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    • This reaction was a modification of reductive deamination reported by Nair and Chamberlain, see Nair, V.; Chamberlain, S. D. Synthesis 1984, 401-403.
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    • note
    • As in the case of 13, treatment of 12 with methanolic ammonia did not give the diamino derivative 11.
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    • References for the synthesis of phosphoramidites: (a) Kamaike, K.; Hasegawa, Y.; Ishido, Y. Nucleosides Nucleotides 1988, 7, 37-43. (b) Froehler, B. C.; Matteucci, M. D. Nucleic Acids Res. 1983, 11, 8031-8036. (c) Caruthers, M. H.; McBride, L. J.; Bracco, L. P.; Dubendorff, J. W. Nucleosides Nucleotides 1985, 4, 95-105.
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    • References for the synthesis of phosphoramidites: (a) Kamaike, K.; Hasegawa, Y.; Ishido, Y. Nucleosides Nucleotides 1988, 7, 37-43. (b) Froehler, B. C.; Matteucci, M. D. Nucleic Acids Res. 1983, 11, 8031-8036. (c) Caruthers, M. H.; McBride, L. J.; Bracco, L. P.; Dubendorff, J. W. Nucleosides Nucleotides 1985, 4, 95-105.
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    • Froehler, B.C.1    Matteucci, M.D.2
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    • References for the synthesis of phosphoramidites: (a) Kamaike, K.; Hasegawa, Y.; Ishido, Y. Nucleosides Nucleotides 1988, 7, 37-43. (b) Froehler, B. C.; Matteucci, M. D. Nucleic Acids Res. 1983, 11, 8031-8036. (c) Caruthers, M. H.; McBride, L. J.; Bracco, L. P.; Dubendorff, J. W. Nucleosides Nucleotides 1985, 4, 95-105.
    • (1985) Nucleosides Nucleotides , vol.4 , pp. 95-105
    • Caruthers, M.H.1    McBride, L.J.2    Bracco, L.P.3    Dubendorff, J.W.4
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    • note
    • O; see ref 11.
  • 76
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    • note
    • The synthesis of IQ was done via the Stille coupling reaction of 1-(2-deoxy-3,5-di-O-triisopropylsilyl-β-D-ribofuranosyl) -5-iodoimidazole-4-carbonitrile with N-acetyl-2-tributylstannylaniline: see Supporting Information.


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