Highly efficient complexations of a porphyrin dimer with remarkably small differences between nucleosides and nucleotides/the predominance of stacking interactions for nucleic acid components [3]

Journal of the American Chemical Society

Volumn 122, Issue 24, 2000, Pages 5881-5882

  Sirish, Mallena ^a   Schneider, Hans Jörg ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE; NUCLEOTIDE; PORPHYRIN DERIVATIVE;

COMPLEX FORMATION; DILUTION; LETTER; MOLECULAR INTERACTION; STRUCTURE ANALYSIS; TITRIMETRY;

EID: 0034697641     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000208k     Document Type: Letter

References (34)

1. For reviews see: (a) Supramolecular Chemistry of Anions; Bianchi, A., Bowman-James, K., Garcia-Espana, E., Eds.; Wiley-VCH: New York, NY, 1997; pp 355-419. (b) Diederich, F. Cyclophanes; Royal Society of Chemistry: Cambridge, 1991. (c) Rebek, J., Jr. Acc. Chem. Res. 1990, 23, 399. Hamilton, A. D. Bioorganic Chemistry Frontiers; Dugas, H., Ed.; Springer: Berlin, Heidelberg, 1991; Vol. 2, p 115.
2. For reviews see: (a) Supramolecular Chemistry of Anions; Bianchi, A., Bowman-James, K., Garcia-Espana, E., Eds.; Wiley-VCH: New York, NY, 1997; pp 355-419. (b) Diederich, F. Cyclophanes; Royal Society of Chemistry: Cambridge, 1991. (c) Rebek, J., Jr. Acc. Chem. Res. 1990, 23, 399. Hamilton, A. D. Bioorganic Chemistry Frontiers; Dugas, H., Ed.; Springer: Berlin, Heidelberg, 1991; Vol. 2, p 115.
3. For reviews see: (a) Supramolecular Chemistry of Anions; Bianchi, A., Bowman-James, K., Garcia-Espana, E., Eds.; Wiley-VCH: New York, NY, 1997; pp 355-419. (b) Diederich, F. Cyclophanes; Royal Society of Chemistry: Cambridge, 1991. (c) Rebek, J., Jr. Acc. Chem. Res. 1990, 23, 399. Hamilton, A. D. Bioorganic Chemistry Frontiers; Dugas, H., Ed.; Springer: Berlin, Heidelberg, 1991; Vol. 2, p 115.
4. For reviews see: (a) Supramolecular Chemistry of Anions; Bianchi, A., Bowman-James, K., Garcia-Espana, E., Eds.; Wiley-VCH: New York, NY, 1997; pp 355-419. (b) Diederich, F. Cyclophanes; Royal Society of Chemistry: Cambridge, 1991. (c) Rebek, J., Jr. Acc. Chem. Res. 1990, 23, 399. Hamilton, A. D. Bioorganic Chemistry Frontiers; Dugas, H., Ed.; Springer: Berlin, Heidelberg, 1991; Vol. 2, p 115.
5. For recent references on nucleotide receptors, usually dominated by ion-pairing, see: (a) Shi, Y.; Schneider, H.-J. J. Chem. Soc., Perkin Trans. 2 1999, 1797. (b) Schwinte, P.; Darcy, R.; Okeeffe, F. J. Chem. Soc., Perkin Trans. 2 1998, 805. (c) Nation, D. A.; Lu, Q.; Martell, A. E. Inorg. Chim. Acta 1997, 263, 209. Aguil, J. A.; Garcia-Espana, E.; Guerrero, J. A.; Luis, S. V. Inorg. Chim. Acta 1996, 246, 287. (e) Ragunathan, K. G.; Schneider, H.-J. J. Chem. Soc., Perkin Trans. 2 1996, 2597. (f) Eliseev, A. V.; Schneider, H.-J. J. Am. Chem. Soc. 1994, 116, 6081. (g) Dhaenens, M.; Lehn, J. M.; Vigneron, J. P. Perkin Trans. 2 1993, 1379.
6. For recent references on nucleotide receptors, usually dominated by ion-pairing, see: (a) Shi, Y.; Schneider, H.-J. J. Chem. Soc., Perkin Trans. 2 1999, 1797. (b) Schwinte, P.; Darcy, R.; Okeeffe, F. J. Chem. Soc., Perkin Trans. 2 1998, 805. (c) Nation, D. A.; Lu, Q.; Martell, A. E. Inorg. Chim. Acta 1997, 263, 209. Aguil, J. A.; Garcia-Espana, E.; Guerrero, J. A.; Luis, S. V. Inorg. Chim. Acta 1996, 246, 287. (e) Ragunathan, K. G.; Schneider, H.-J. J. Chem. Soc., Perkin Trans. 2 1996, 2597. (f) Eliseev, A. V.; Schneider, H.-J. J. Am. Chem. Soc. 1994, 116, 6081. (g) Dhaenens, M.; Lehn, J. M.; Vigneron, J. P. Perkin Trans. 2 1993, 1379.
7. For recent references on nucleotide receptors, usually dominated by ion-pairing, see: (a) Shi, Y.; Schneider, H.-J. J. Chem. Soc., Perkin Trans. 2 1999, 1797. (b) Schwinte, P.; Darcy, R.; Okeeffe, F. J. Chem. Soc., Perkin Trans. 2 1998, 805. (c) Nation, D. A.; Lu, Q.; Martell, A. E. Inorg. Chim. Acta 1997, 263, 209. Aguil, J. A.; Garcia-Espana, E.; Guerrero, J. A.; Luis, S. V. Inorg. Chim. Acta 1996, 246, 287. (e) Ragunathan, K. G.; Schneider, H.-J. J. Chem. Soc., Perkin Trans. 2 1996, 2597. (f) Eliseev, A. V.; Schneider, H.-J. J. Am. Chem. Soc. 1994, 116, 6081. (g) Dhaenens, M.; Lehn, J. M.; Vigneron, J. P. Perkin Trans. 2 1993, 1379.
8. For recent references on nucleotide receptors, usually dominated by ion-pairing, see: (a) Shi, Y.; Schneider, H.-J. J. Chem. Soc., Perkin Trans. 2 1999, 1797. (b) Schwinte, P.; Darcy, R.; Okeeffe, F. J. Chem. Soc., Perkin Trans. 2 1998, 805. (c) Nation, D. A.; Lu, Q.; Martell, A. E. Inorg. Chim. Acta 1997, 263, 209. Aguil, J. A.; Garcia-Espana, E.; Guerrero, J. A.; Luis, S. V. Inorg. Chim. Acta 1996, 246, 287. (e) Ragunathan, K. G.; Schneider, H.-J. J. Chem. Soc., Perkin Trans. 2 1996, 2597. (f) Eliseev, A. V.; Schneider, H.-J. J. Am. Chem. Soc. 1994, 116, 6081. (g) Dhaenens, M.; Lehn, J. M.; Vigneron, J. P. Perkin Trans. 2 1993, 1379.
9. For recent references on nucleotide receptors, usually dominated by ion-pairing, see: (a) Shi, Y.; Schneider, H.-J. J. Chem. Soc., Perkin Trans. 2 1999, 1797. (b) Schwinte, P.; Darcy, R.; Okeeffe, F. J. Chem. Soc., Perkin Trans. 2 1998, 805. (c) Nation, D. A.; Lu, Q.; Martell, A. E. Inorg. Chim. Acta 1997, 263, 209. Aguil, J. A.; Garcia-Espana, E.; Guerrero, J. A.; Luis, S. V. Inorg. Chim. Acta 1996, 246, 287. (e) Ragunathan, K. G.; Schneider, H.-J. J. Chem. Soc., Perkin Trans. 2 1996, 2597. (f) Eliseev, A. V.; Schneider, H.-J. J. Am. Chem. Soc. 1994, 116, 6081. (g) Dhaenens, M.; Lehn, J. M.; Vigneron, J. P. Perkin Trans. 2 1993, 1379.
10. For recent references on nucleotide receptors, usually dominated by ion-pairing, see: (a) Shi, Y.; Schneider, H.-J. J. Chem. Soc., Perkin Trans. 2 1999, 1797. (b) Schwinte, P.; Darcy, R.; Okeeffe, F. J. Chem. Soc., Perkin Trans. 2 1998, 805. (c) Nation, D. A.; Lu, Q.; Martell, A. E. Inorg. Chim. Acta 1997, 263, 209. Aguil, J. A.; Garcia-Espana, E.; Guerrero, J. A.; Luis, S. V. Inorg. Chim. Acta 1996, 246, 287. (e) Ragunathan, K. G.; Schneider, H.-J. J. Chem. Soc., Perkin Trans. 2 1996, 2597. (f) Eliseev, A. V.; Schneider, H.-J. J. Am. Chem. Soc. 1994, 116, 6081. (g) Dhaenens, M.; Lehn, J. M.; Vigneron, J. P. Perkin Trans. 2 1993, 1379.
11. For recent references on nucleotide receptors, usually dominated by ion-pairing, see: (a) Shi, Y.; Schneider, H.-J. J. Chem. Soc., Perkin Trans. 2 1999, 1797. (b) Schwinte, P.; Darcy, R.; Okeeffe, F. J. Chem. Soc., Perkin Trans. 2 1998, 805. (c) Nation, D. A.; Lu, Q.; Martell, A. E. Inorg. Chim. Acta 1997, 263, 209. Aguil, J. A.; Garcia-Espana, E.; Guerrero, J. A.; Luis, S. V. Inorg. Chim. Acta 1996, 246, 287. (e) Ragunathan, K. G.; Schneider, H.-J. J. Chem. Soc., Perkin Trans. 2 1996, 2597. (f) Eliseev, A. V.; Schneider, H.-J. J. Am. Chem. Soc. 1994, 116, 6081. (g) Dhaenens, M.; Lehn, J. M.; Vigneron, J. P. Perkin Trans. 2 1993, 1379.
12. For recent references on complexation with electroneutral nucleosides or nucleobase derivatives see: (a) Yu, L.; Schneider, H.-J. Eur. J. Org. Chem. 1999, 1619. (b) Conn, M. M.; Deslongchamps, G.; Mendoza, J. de; Rebek, J., Jr. J. Am. Chem. Soc. 1993, 115, 3548. (c) Rotello, V. M.; Viani, E. A.; Deslongchamps, G.; Murray, B. A.; Rebek, J., Jr. J. Am. Chem. Soc. 1993, 115, 797. (d) Jeong, K. S.; Tjivikua, T.; Muehldorf, A.; Deslongchamps, G.; Famulok, M.; Rebek, J., Jr. J. Am. Chem. Soc. 1991, 113, 201. (e) Hamilton, A. D.; Little, D. J. Chem. Soc., Chem. Commun. 1990, 297. (f) Inouye, M.; Itoh, M. S.; Nakazumi, H. J. Org. Chem. 1999, 64, 9393.
13. For recent references on complexation with electroneutral nucleosides or nucleobase derivatives see: (a) Yu, L.; Schneider, H.-J. Eur. J. Org. Chem. 1999, 1619. (b) Conn, M. M.; Deslongchamps, G.; Mendoza, J. de; Rebek, J., Jr. J. Am. Chem. Soc. 1993, 115, 3548. (c) Rotello, V. M.; Viani, E. A.; Deslongchamps, G.; Murray, B. A.; Rebek, J., Jr. J. Am. Chem. Soc. 1993, 115, 797. (d) Jeong, K. S.; Tjivikua, T.; Muehldorf, A.; Deslongchamps, G.; Famulok, M.; Rebek, J., Jr. J. Am. Chem. Soc. 1991, 113, 201. (e) Hamilton, A. D.; Little, D. J. Chem. Soc., Chem. Commun. 1990, 297. (f) Inouye, M.; Itoh, M. S.; Nakazumi, H. J. Org. Chem. 1999, 64, 9393.
14. For recent references on complexation with electroneutral nucleosides or nucleobase derivatives see: (a) Yu, L.; Schneider, H.-J. Eur. J. Org. Chem. 1999, 1619. (b) Conn, M. M.; Deslongchamps, G.; Mendoza, J. de; Rebek, J., Jr. J. Am. Chem. Soc. 1993, 115, 3548. (c) Rotello, V. M.; Viani, E. A.; Deslongchamps, G.; Murray, B. A.; Rebek, J., Jr. J. Am. Chem. Soc. 1993, 115, 797. (d) Jeong, K. S.; Tjivikua, T.; Muehldorf, A.; Deslongchamps, G.; Famulok, M.; Rebek, J., Jr. J. Am. Chem. Soc. 1991, 113, 201. (e) Hamilton, A. D.; Little, D. J. Chem. Soc., Chem. Commun. 1990, 297. (f) Inouye, M.; Itoh, M. S.; Nakazumi, H. J. Org. Chem. 1999, 64, 9393.
15. For recent references on complexation with electroneutral nucleosides or nucleobase derivatives see: (a) Yu, L.; Schneider, H.-J. Eur. J. Org. Chem. 1999, 1619. (b) Conn, M. M.; Deslongchamps, G.; Mendoza, J. de; Rebek, J., Jr. J. Am. Chem. Soc. 1993, 115, 3548. (c) Rotello, V. M.; Viani, E. A.; Deslongchamps, G.; Murray, B. A.; Rebek, J., Jr. J. Am. Chem. Soc. 1993, 115, 797. (d) Jeong, K. S.; Tjivikua, T.; Muehldorf, A.; Deslongchamps, G.; Famulok, M.; Rebek, J., Jr. J. Am. Chem. Soc. 1991, 113, 201. (e) Hamilton, A. D.; Little, D. J. Chem. Soc., Chem. Commun. 1990, 297. (f) Inouye, M.; Itoh, M. S.; Nakazumi, H. J. Org. Chem. 1999, 64, 9393.
16. For recent references on complexation with electroneutral nucleosides or nucleobase derivatives see: (a) Yu, L.; Schneider, H.-J. Eur. J. Org. Chem. 1999, 1619. (b) Conn, M. M.; Deslongchamps, G.; Mendoza, J. de; Rebek, J., Jr. J. Am. Chem. Soc. 1993, 115, 3548. (c) Rotello, V. M.; Viani, E. A.; Deslongchamps, G.; Murray, B. A.; Rebek, J., Jr. J. Am. Chem. Soc. 1993, 115, 797. (d) Jeong, K. S.; Tjivikua, T.; Muehldorf, A.; Deslongchamps, G.; Famulok, M.; Rebek, J., Jr. J. Am. Chem. Soc. 1991, 113, 201. (e) Hamilton, A. D.; Little, D. J. Chem. Soc., Chem. Commun. 1990, 297. (f) Inouye, M.; Itoh, M. S.; Nakazumi, H. J. Org. Chem. 1999, 64, 9393.
17. For recent references on complexation with electroneutral nucleosides or nucleobase derivatives see: (a) Yu, L.; Schneider, H.-J. Eur. J. Org. Chem. 1999, 1619. (b) Conn, M. M.; Deslongchamps, G.; Mendoza, J. de; Rebek, J., Jr. J. Am. Chem. Soc. 1993, 115, 3548. (c) Rotello, V. M.; Viani, E. A.; Deslongchamps, G.; Murray, B. A.; Rebek, J., Jr. J. Am. Chem. Soc. 1993, 115, 797. (d) Jeong, K. S.; Tjivikua, T.; Muehldorf, A.; Deslongchamps, G.; Famulok, M.; Rebek, J., Jr. J. Am. Chem. Soc. 1991, 113, 201. (e) Hamilton, A. D.; Little, D. J. Chem. Soc., Chem. Commun. 1990, 297. (f) Inouye, M.; Itoh, M. S.; Nakazumi, H. J. Org. Chem. 1999, 64, 9393.
18. General references on the use of porphyrin and analogues for supramolecular complexes see: (a) Sessler, J. L.; Sansom, P. I.; Andrievsky, A.; Kral, V. in ref 1a, p 355ff. For porphyrin dimers see: (b) Elemans, J. A. A. J. Org. Chem. 1999, 64, 7009. (c) Twyman, L. J. Tetrahedron Lett. 1999, 40, 6681. (d) Baudin, O. J. Org. Chem. 1997, 62, 5458. (e) Graça, M. Chem. Commun. 1999, 1771.
19. General references on the use of porphyrin and analogues for supramolecular complexes see: (a) Sessler, J. L.; Sansom, P. I.; Andrievsky, A.; Kral, V. in ref 1a, p 355ff. For porphyrin dimers see: (b) Elemans, J. A. A. J. Org. Chem. 1999, 64, 7009. (c) Twyman, L. J. Tetrahedron Lett. 1999, 40, 6681. (d) Baudin, O. J. Org. Chem. 1997, 62, 5458. (e) Graça, M. Chem. Commun. 1999, 1771.
20. General references on the use of porphyrin and analogues for supramolecular complexes see: (a) Sessler, J. L.; Sansom, P. I.; Andrievsky, A.; Kral, V. in ref 1a, p 355ff. For porphyrin dimers see: (b) Elemans, J. A. A. J. Org. Chem. 1999, 64, 7009. (c) Twyman, L. J. Tetrahedron Lett. 1999, 40, 6681. (d) Baudin, O. J. Org. Chem. 1997, 62, 5458. (e) Graça, M. Chem. Commun. 1999, 1771.
21. General references on the use of porphyrin and analogues for supramolecular complexes see: (a) Sessler, J. L.; Sansom, P. I.; Andrievsky, A.; Kral, V. in ref 1a, p 355ff. For porphyrin dimers see: (b) Elemans, J. A. A. J. Org. Chem. 1999, 64, 7009. (c) Twyman, L. J. Tetrahedron Lett. 1999, 40, 6681. (d) Baudin, O. J. Org. Chem. 1997, 62, 5458. (e) Graça, M. Chem. Commun. 1999, 1771.
22. General references on the use of porphyrin and analogues for supramolecular complexes see: (a) Sessler, J. L.; Sansom, P. I.; Andrievsky, A.; Kral, V. in ref 1a, p 355ff. For porphyrin dimers see: (b) Elemans, J. A. A. J. Org. Chem. 1999, 64, 7009. (c) Twyman, L. J. Tetrahedron Lett. 1999, 40, 6681. (d) Baudin, O. J. Org. Chem. 1997, 62, 5458. (e) Graça, M. Chem. Commun. 1999, 1771.
23. Nucleotide complexation with porphyrin and related host compounds: (a) Pasternack, R. F.; Gibbs, E. J., Gaudemer, A.; Antebi, A.; Bassner, S.; De Poy, L.; Turner, D. H.; Williams, A.; Laplace, F.; Lansard, M. H.; Merienne, C.; Perree-Fauvet, M. J. Am. Chem. Soc. 1985, 107, 8179. (b) Kral, V.; Andrievsky, A.; Sessler, J. L. Chem. Com. 1995, 2349.
24. Nucleotide complexation with porphyrin and related host compounds: (a) Pasternack, R. F.; Gibbs, E. J., Gaudemer, A.; Antebi, A.; Bassner, S.; De Poy, L.; Turner, D. H.; Williams, A.; Laplace, F.; Lansard, M. H.; Merienne, C.; Perree-Fauvet, M. J. Am. Chem. Soc. 1985, 107, 8179. (b) Kral, V.; Andrievsky, A.; Sessler, J. L. Chem. Com. 1995, 2349.
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27. For other cases of dominating stacking interactions in nucleotide complexes see: (a) Constant, J. F.; Fahy, J.; Lhomme, J.; Anderson, J. E. Tetrahedron Lett. 1987, 28, 1777. (b) Zinic, M.; Tomišic, V.; Simeon, V.; Vigneron, J.-P.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1995, 1073. (c) Lorente, A.; Fernandez-Saiz, M.; Lehn, J.-M.; Vigneron, J.-P. Tetrahedron Lett. 1995, 36, 8279. Baudoin, O.; Teulade-Fichou, M.-P.; Vigneron, J.- P.; Lehn, J.-M. J. Org. Chem. 1997, 62, 5458.
28. For other cases of dominating stacking interactions in nucleotide complexes see: (a) Constant, J. F.; Fahy, J.; Lhomme, J.; Anderson, J. E. Tetrahedron Lett. 1987, 28, 1777. (b) Zinic, M.; Tomišic, V.; Simeon, V.; Vigneron, J.-P.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1995, 1073. (c) Lorente, A.; Fernandez-Saiz, M.; Lehn, J.-M.; Vigneron, J.-P. Tetrahedron Lett. 1995, 36, 8279. Baudoin, O.; Teulade-Fichou, M.-P.; Vigneron, J.- P.; Lehn, J.-M. J. Org. Chem. 1997, 62, 5458.
29. For other cases of dominating stacking interactions in nucleotide complexes see: (a) Constant, J. F.; Fahy, J.; Lhomme, J.; Anderson, J. E. Tetrahedron Lett. 1987, 28, 1777. (b) Zinic, M.; Tomišic, V.; Simeon, V.; Vigneron, J.-P.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1995, 1073. (c) Lorente, A.; Fernandez-Saiz, M.; Lehn, J.-M.; Vigneron, J.-P. Tetrahedron Lett. 1995, 36, 8279. Baudoin, O.; Teulade-Fichou, M.-P.; Vigneron, J.- P.; Lehn, J.-M. J. Org. Chem. 1997, 62, 5458.
30. For other cases of dominating stacking interactions in nucleotide complexes see: (a) Constant, J. F.; Fahy, J.; Lhomme, J.; Anderson, J. E. Tetrahedron Lett. 1987, 28, 1777. (b) Zinic, M.; Tomišic, V.; Simeon, V.; Vigneron, J.-P.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1995, 1073. (c) Lorente, A.; Fernandez-Saiz, M.; Lehn, J.-M.; Vigneron, J.-P. Tetrahedron Lett. 1995, 36, 8279. Baudoin, O.; Teulade-Fichou, M.-P.; Vigneron, J.-P.; Lehn, J.-M. J. Org. Chem. 1997, 62, 5458.
31. Sirish, M.; Schneider, H.-J. Chem. Commun. 2000, 23.
32. For an early model system, see: ref 7a.
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34. Schneider, H.-J.; Wang, M. J. Org. Chem. 1994, 59, 7454.