Novel guanosine-cytidine dinucleoside that self-assembles into a trimeric supramolecule

Organic Letters

Volumn 5, Issue 15, 2003, Pages 2627-2630

  Sessler, Jonathan L ^a   Jayawickramarajah, Janarthanan ^a   Sathiosatham, Muhunthan ^a   Sherman, Courtney L ^a   Brodbelt, Jennifer S ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GUANOSINE CYTIDINE DINUCLEOSIDE; NUCLEOSIDE DERIVATIVE; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; GEL PERMEATION CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; VAPOR PRESSURE;

CHROMATOGRAPHY, GEL; CYTIDINE; GUANOSINE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR WEIGHT; PALLADIUM; PRESSURE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; VOLATILIZATION;

EID: 0141631582     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034765y     Document Type: Article

References (38)

1. For reviews, see: (a) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (b) Lehn, J.-M. Polym. Int. 2002, 51, 825-839. (c) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2383-2426. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) Fredericks, J. R.; Hamilton, A. D. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Ed.; Pergamon: New York, 1996; Vol. 9, pp 565-594. (f) Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097. For representative cyclic oligomers of particular interest, see: (g) Yang, J.; Fan, E.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 5314-5315. (h) Zafar, A.; Geib, S. J.; Hamuro, Y.; Hamilton, A. D. New. J. Chem. 1998, 137-141. (i) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (j) Forman, S. L.; Fettinger, J. C.; Pieraccini, S.; Gottarelli, G.; Davis, J. T. J. Am. Chem. Soc. 2000, 122, 4060-4067. (k) Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215-2217. (l) Sontjens, S. H. M.; Sijbesma, R. P.; van Genderen, M. H. P.; Meijer, E. W. Macromolecules 2001, 34, 3815-3818. (m) Mascal, M.; Hext, N. M.; Warmuth, R.; Moore, M. H.; Turkenburg, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 2204-2206. (n) Boucher, E.; Simard, M.; Wuest, J. D. J. Org. Chem. 1995, 60, 1408-1412. (o) Zerkowski, J. A.; Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 5473-5475.
2. For reviews, see: (a) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (b) Lehn, J.-M. Polym. Int. 2002, 51, 825-839. (c) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2383-2426. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) Fredericks, J. R.; Hamilton, A. D. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Ed.; Pergamon: New York, 1996; Vol. 9, pp 565-594. (f) Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097. For representative cyclic oligomers of particular interest, see: (g) Yang, J.; Fan, E.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 5314-5315. (h) Zafar, A.; Geib, S. J.; Hamuro, Y.; Hamilton, A. D. New. J. Chem. 1998, 137-141. (i) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (j) Forman, S. L.; Fettinger, J. C.; Pieraccini, S.; Gottarelli, G.; Davis, J. T. J. Am. Chem. Soc. 2000, 122, 4060-4067. (k) Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215-2217. (l) Sontjens, S. H. M.; Sijbesma, R. P.; van Genderen, M. H. P.; Meijer, E. W. Macromolecules 2001, 34, 3815-3818. (m) Mascal, M.; Hext, N. M.; Warmuth, R.; Moore, M. H.; Turkenburg, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 2204-2206. (n) Boucher, E.; Simard, M.; Wuest, J. D. J. Org. Chem. 1995, 60, 1408-1412. (o) Zerkowski, J. A.; Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 5473-5475.
3. For reviews, see: (a) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (b) Lehn, J.-M. Polym. Int. 2002, 51, 825-839. (c) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2383-2426. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) Fredericks, J. R.; Hamilton, A. D. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Ed.; Pergamon: New York, 1996; Vol. 9, pp 565-594. (f) Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097. For representative cyclic oligomers of particular interest, see: (g) Yang, J.; Fan, E.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 5314-5315. (h) Zafar, A.; Geib, S. J.; Hamuro, Y.; Hamilton, A. D. New. J. Chem. 1998, 137-141. (i) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (j) Forman, S. L.; Fettinger, J. C.; Pieraccini, S.; Gottarelli, G.; Davis, J. T. J. Am. Chem. Soc. 2000, 122, 4060-4067. (k) Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215-2217. (l) Sontjens, S. H. M.; Sijbesma, R. P.; van Genderen, M. H. P.; Meijer, E. W. Macromolecules 2001, 34, 3815-3818. (m) Mascal, M.; Hext, N. M.; Warmuth, R.; Moore, M. H.; Turkenburg, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 2204-2206. (n) Boucher, E.; Simard, M.; Wuest, J. D. J. Org. Chem. 1995, 60, 1408-1412. (o) Zerkowski, J. A.; Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 5473-5475.
4. For reviews, see: (a) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (b) Lehn, J.-M. Polym. Int. 2002, 51, 825-839. (c) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2383-2426. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) Fredericks, J. R.; Hamilton, A. D. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Ed.; Pergamon: New York, 1996; Vol. 9, pp 565-594. (f) Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097. For representative cyclic oligomers of particular interest, see: (g) Yang, J.; Fan, E.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 5314-5315. (h) Zafar, A.; Geib, S. J.; Hamuro, Y.; Hamilton, A. D. New. J. Chem. 1998, 137-141. (i) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (j) Forman, S. L.; Fettinger, J. C.; Pieraccini, S.; Gottarelli, G.; Davis, J. T. J. Am. Chem. Soc. 2000, 122, 4060-4067. (k) Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215-2217. (l) Sontjens, S. H. M.; Sijbesma, R. P.; van Genderen, M. H. P.; Meijer, E. W. Macromolecules 2001, 34, 3815-3818. (m) Mascal, M.; Hext, N. M.; Warmuth, R.; Moore, M. H.; Turkenburg, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 2204-2206. (n) Boucher, E.; Simard, M.; Wuest, J. D. J. Org. Chem. 1995, 60, 1408-1412. (o) Zerkowski, J. A.; Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 5473-5475.
5. For reviews, see: (a) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (b) Lehn, J.-M. Polym. Int. 2002, 51, 825-839. (c) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2383-2426. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) Fredericks, J. R.; Hamilton, A. D. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Ed.; Pergamon: New York, 1996; Vol. 9, pp 565-594. (f) Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097. For representative cyclic oligomers of particular interest, see: (g) Yang, J.; Fan, E.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 5314-5315. (h) Zafar, A.; Geib, S. J.; Hamuro, Y.; Hamilton, A. D. New. J. Chem. 1998, 137-141. (i) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (j) Forman, S. L.; Fettinger, J. C.; Pieraccini, S.; Gottarelli, G.; Davis, J. T. J. Am. Chem. Soc. 2000, 122, 4060-4067. (k) Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215-2217. (l) Sontjens, S. H. M.; Sijbesma, R. P.; van Genderen, M. H. P.; Meijer, E. W. Macromolecules 2001, 34, 3815-3818. (m) Mascal, M.; Hext, N. M.; Warmuth, R.; Moore, M. H.; Turkenburg, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 2204-2206. (n) Boucher, E.; Simard, M.; Wuest, J. D. J. Org. Chem. 1995, 60, 1408-1412. (o) Zerkowski, J. A.; Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 5473-5475.
6. For reviews, see: (a) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (b) Lehn, J.-M. Polym. Int. 2002, 51, 825-839. (c) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2383-2426. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) Fredericks, J. R.; Hamilton, A. D. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Ed.; Pergamon: New York, 1996; Vol. 9, pp 565-594. (f) Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097. For representative cyclic oligomers of particular interest, see: (g) Yang, J.; Fan, E.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 5314-5315. (h) Zafar, A.; Geib, S. J.; Hamuro, Y.; Hamilton, A. D. New. J. Chem. 1998, 137-141. (i) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (j) Forman, S. L.; Fettinger, J. C.; Pieraccini, S.; Gottarelli, G.; Davis, J. T. J. Am. Chem. Soc. 2000, 122, 4060-4067. (k) Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215-2217. (l) Sontjens, S. H. M.; Sijbesma, R. P.; van Genderen, M. H. P.; Meijer, E. W. Macromolecules 2001, 34, 3815-3818. (m) Mascal, M.; Hext, N. M.; Warmuth, R.; Moore, M. H.; Turkenburg, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 2204-2206. (n) Boucher, E.; Simard, M.; Wuest, J. D. J. Org. Chem. 1995, 60, 1408-1412. (o) Zerkowski, J. A.; Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 5473-5475.
7. For reviews, see: (a) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (b) Lehn, J.-M. Polym. Int. 2002, 51, 825-839. (c) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2383-2426. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) Fredericks, J. R.; Hamilton, A. D. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Ed.; Pergamon: New York, 1996; Vol. 9, pp 565-594. (f) Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097. For representative cyclic oligomers of particular interest, see: (g) Yang, J.; Fan, E.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 5314-5315. (h) Zafar, A.; Geib, S. J.; Hamuro, Y.; Hamilton, A. D. New. J. Chem. 1998, 137-141. (i) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (j) Forman, S. L.; Fettinger, J. C.; Pieraccini, S.; Gottarelli, G.; Davis, J. T. J. Am. Chem. Soc. 2000, 122, 4060-4067. (k) Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215-2217. (l) Sontjens, S. H. M.; Sijbesma, R. P.; van Genderen, M. H. P.; Meijer, E. W. Macromolecules 2001, 34, 3815-3818. (m) Mascal, M.; Hext, N. M.; Warmuth, R.; Moore, M. H.; Turkenburg, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 2204-2206. (n) Boucher, E.; Simard, M.; Wuest, J. D. J. Org. Chem. 1995, 60, 1408-1412. (o) Zerkowski, J. A.; Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 5473-5475.
8. For reviews, see: (a) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (b) Lehn, J.-M. Polym. Int. 2002, 51, 825-839. (c) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2383-2426. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) Fredericks, J. R.; Hamilton, A. D. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Ed.; Pergamon: New York, 1996; Vol. 9, pp 565-594. (f) Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097. For representative cyclic oligomers of particular interest, see: (g) Yang, J.; Fan, E.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 5314-5315. (h) Zafar, A.; Geib, S. J.; Hamuro, Y.; Hamilton, A. D. New. J. Chem. 1998, 137-141. (i) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (j) Forman, S. L.; Fettinger, J. C.; Pieraccini, S.; Gottarelli, G.; Davis, J. T. J. Am. Chem. Soc. 2000, 122, 4060-4067. (k) Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215-2217. (l) Sontjens, S. H. M.; Sijbesma, R. P.; van Genderen, M. H. P.; Meijer, E. W. Macromolecules 2001, 34, 3815-3818. (m) Mascal, M.; Hext, N. M.; Warmuth, R.; Moore, M. H.; Turkenburg, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 2204-2206. (n) Boucher, E.; Simard, M.; Wuest, J. D. J. Org. Chem. 1995, 60, 1408-1412. (o) Zerkowski, J. A.; Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 5473-5475.
9. For reviews, see: (a) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (b) Lehn, J.-M. Polym. Int. 2002, 51, 825-839. (c) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2383-2426. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) Fredericks, J. R.; Hamilton, A. D. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Ed.; Pergamon: New York, 1996; Vol. 9, pp 565-594. (f) Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097. For representative cyclic oligomers of particular interest, see: (g) Yang, J.; Fan, E.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 5314-5315. (h) Zafar, A.; Geib, S. J.; Hamuro, Y.; Hamilton, A. D. New. J. Chem. 1998, 137-141. (i) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (j) Forman, S. L.; Fettinger, J. C.; Pieraccini, S.; Gottarelli, G.; Davis, J. T. J. Am. Chem. Soc. 2000, 122, 4060-4067. (k) Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215-2217. (l) Sontjens, S. H. M.; Sijbesma, R. P.; van Genderen, M. H. P.; Meijer, E. W. Macromolecules 2001, 34, 3815-3818. (m) Mascal, M.; Hext, N. M.; Warmuth, R.; Moore, M. H.; Turkenburg, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 2204-2206. (n) Boucher, E.; Simard, M.; Wuest, J. D. J. Org. Chem. 1995, 60, 1408-1412. (o) Zerkowski, J. A.; Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 5473-5475.
10. For reviews, see: (a) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (b) Lehn, J.-M. Polym. Int. 2002, 51, 825-839. (c) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2383-2426. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) Fredericks, J. R.; Hamilton, A. D. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Ed.; Pergamon: New York, 1996; Vol. 9, pp 565-594. (f) Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097. For representative cyclic oligomers of particular interest, see: (g) Yang, J.; Fan, E.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 5314-5315. (h) Zafar, A.; Geib, S. J.; Hamuro, Y.; Hamilton, A. D. New. J. Chem. 1998, 137-141. (i) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (j) Forman, S. L.; Fettinger, J. C.; Pieraccini, S.; Gottarelli, G.; Davis, J. T. J. Am. Chem. Soc. 2000, 122, 4060-4067. (k) Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215-2217. (l) Sontjens, S. H. M.; Sijbesma, R. P.; van Genderen, M. H. P.; Meijer, E. W. Macromolecules 2001, 34, 3815-3818. (m) Mascal, M.; Hext, N. M.; Warmuth, R.; Moore, M. H.; Turkenburg, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 2204-2206. (n) Boucher, E.; Simard, M.; Wuest, J. D. J. Org. Chem. 1995, 60, 1408-1412. (o) Zerkowski, J. A.; Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 5473-5475.
11. For reviews, see: (a) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (b) Lehn, J.-M. Polym. Int. 2002, 51, 825-839. (c) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2383-2426. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) Fredericks, J. R.; Hamilton, A. D. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Ed.; Pergamon: New York, 1996; Vol. 9, pp 565-594. (f) Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097. For representative cyclic oligomers of particular interest, see: (g) Yang, J.; Fan, E.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 5314-5315. (h) Zafar, A.; Geib, S. J.; Hamuro, Y.; Hamilton, A. D. New. J. Chem. 1998, 137-141. (i) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (j) Forman, S. L.; Fettinger, J. C.; Pieraccini, S.; Gottarelli, G.; Davis, J. T. J. Am. Chem. Soc. 2000, 122, 4060-4067. (k) Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215-2217. (l) Sontjens, S. H. M.; Sijbesma, R. P.; van Genderen, M. H. P.; Meijer, E. W. Macromolecules 2001, 34, 3815-3818. (m) Mascal, M.; Hext, N. M.; Warmuth, R.; Moore, M. H.; Turkenburg, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 2204-2206. (n) Boucher, E.; Simard, M.; Wuest, J. D. J. Org. Chem. 1995, 60, 1408-1412. (o) Zerkowski, J. A.; Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 5473-5475.
12. For reviews, see: (a) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (b) Lehn, J.-M. Polym. Int. 2002, 51, 825-839. (c) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2383-2426. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) Fredericks, J. R.; Hamilton, A. D. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Ed.; Pergamon: New York, 1996; Vol. 9, pp 565-594. (f) Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097. For representative cyclic oligomers of particular interest, see: (g) Yang, J.; Fan, E.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 5314-5315. (h) Zafar, A.; Geib, S. J.; Hamuro, Y.; Hamilton, A. D. New. J. Chem. 1998, 137-141. (i) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (j) Forman, S. L.; Fettinger, J. C.; Pieraccini, S.; Gottarelli, G.; Davis, J. T. J. Am. Chem. Soc. 2000, 122, 4060-4067. (k) Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215-2217. (l) Sontjens, S. H. M.; Sijbesma, R. P.; van Genderen, M. H. P.; Meijer, E. W. Macromolecules 2001, 34, 3815-3818. (m) Mascal, M.; Hext, N. M.; Warmuth, R.; Moore, M. H.; Turkenburg, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 2204-2206. (n) Boucher, E.; Simard, M.; Wuest, J. D. J. Org. Chem. 1995, 60, 1408-1412. (o) Zerkowski, J. A.; Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 5473-5475.
13. For reviews, see: (a) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (b) Lehn, J.-M. Polym. Int. 2002, 51, 825-839. (c) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2383-2426. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) Fredericks, J. R.; Hamilton, A. D. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Ed.; Pergamon: New York, 1996; Vol. 9, pp 565-594. (f) Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097. For representative cyclic oligomers of particular interest, see: (g) Yang, J.; Fan, E.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 5314-5315. (h) Zafar, A.; Geib, S. J.; Hamuro, Y.; Hamilton, A. D. New. J. Chem. 1998, 137-141. (i) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (j) Forman, S. L.; Fettinger, J. C.; Pieraccini, S.; Gottarelli, G.; Davis, J. T. J. Am. Chem. Soc. 2000, 122, 4060-4067. (k) Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215-2217. (l) Sontjens, S. H. M.; Sijbesma, R. P.; van Genderen, M. H. P.; Meijer, E. W. Macromolecules 2001, 34, 3815-3818. (m) Mascal, M.; Hext, N. M.; Warmuth, R.; Moore, M. H.; Turkenburg, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 2204-2206. (n) Boucher, E.; Simard, M.; Wuest, J. D. J. Org. Chem. 1995, 60, 1408-1412. (o) Zerkowski, J. A.; Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 5473-5475.
14. For reviews, see: (a) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (b) Lehn, J.-M. Polym. Int. 2002, 51, 825-839. (c) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2383-2426. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) Fredericks, J. R.; Hamilton, A. D. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Ed.; Pergamon: New York, 1996; Vol. 9, pp 565-594. (f) Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097. For representative cyclic oligomers of particular interest, see: (g) Yang, J.; Fan, E.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 5314-5315. (h) Zafar, A.; Geib, S. J.; Hamuro, Y.; Hamilton, A. D. New. J. Chem. 1998, 137-141. (i) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (j) Forman, S. L.; Fettinger, J. C.; Pieraccini, S.; Gottarelli, G.; Davis, J. T. J. Am. Chem. Soc. 2000, 122, 4060-4067. (k) Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215-2217. (l) Sontjens, S. H. M.; Sijbesma, R. P.; van Genderen, M. H. P.; Meijer, E. W. Macromolecules 2001, 34, 3815-3818. (m) Mascal, M.; Hext, N. M.; Warmuth, R.; Moore, M. H.; Turkenburg, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 2204-2206. (n) Boucher, E.; Simard, M.; Wuest, J. D. J. Org. Chem. 1995, 60, 1408-1412. (o) Zerkowski, J. A.; Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 5473-5475.
15. For reviews, see: (a) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (b) Lehn, J.-M. Polym. Int. 2002, 51, 825-839. (c) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2383-2426. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. (e) Fredericks, J. R.; Hamilton, A. D. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Ed.; Pergamon: New York, 1996; Vol. 9, pp 565-594. (f) Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097. For representative cyclic oligomers of particular interest, see: (g) Yang, J.; Fan, E.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 5314-5315. (h) Zafar, A.; Geib, S. J.; Hamuro, Y.; Hamilton, A. D. New. J. Chem. 1998, 137-141. (i) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (j) Forman, S. L.; Fettinger, J. C.; Pieraccini, S.; Gottarelli, G.; Davis, J. T. J. Am. Chem. Soc. 2000, 122, 4060-4067. (k) Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215-2217. (l) Sontjens, S. H. M.; Sijbesma, R. P.; van Genderen, M. H. P.; Meijer, E. W. Macromolecules 2001, 34, 3815-3818. (m) Mascal, M.; Hext, N. M.; Warmuth, R.; Moore, M. H.; Turkenburg, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 2204-2206. (n) Boucher, E.; Simard, M.; Wuest, J. D. J. Org. Chem. 1995, 60, 1408-1412. (o) Zerkowski, J. A.; Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 5473-5475.
16. (a) Sessler, J. L.; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 19, 1300-1303.
17. (b) Sessler, J. L.; Wang, R. Angew. Chem., Int. Ed. 1998, 37, 1726-1729.
18. (c) Sessler, J. L.; Wang, R. J. Org. Chem. 1998, 63, 4079-4091.
19. (d) Schall, O. F.; Gokel, G. W. J. Am. Chem. Soc. 1994, 116, 6089-6100.
20. (e) Chen, H. C.; Ogo, S.; Fish, R. H. J. Am. Chem. Soc. 1996, 118, 4993-5001.
21. (f) Mezzina, E.; Mariana, P.; Itri, R.; Masiero, S.; Pieraccini, S.; Spada, G. S.; Spinozzi, F.; Davis. J. T.; Gottarelli, G. Chem. Eur. J. 2001, 7, 389-395.
22. (g) Drain, C. M.; Fischer, R.; Nolen, E. G.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1993, 243-245.
23. (a) Marsh, A.; Silvestri, M.; Lehn, J.-M. Chem. Commun. 1996, 1527-1528.
24. (b) Mascal, M.; Hext, N. M.; Warmuth, R.; Arnall-Culliford, J. R.; Moore, M. H.; Turkenburg, J. P. J. Org. Chem. 1999, 64, 8479-8484.
25. (c) Ma, Y.; Kolotuchin, S. V.; Zimmerman, S. C. J. Am. Chem. Soc. 2002, 124, 13757-13769.
26. (d) Fenniri, H.; Mathivanan, P.; Vidale, K. L.; Sherman, D. M.; Hallenga, K.; Wood, K. V.; Stowell, J. G. J. Am. Chem. Soc. 2001, 123, 3854-3855.
27. (e) Fenniri, H.; Deng, B.; Ribbe, A. E. J. Am. Chem. Soc. 2002, 124, 11064.
28. Nagatsugi, F.; Uemura, K.; Nakashima, S.; Maeda, M.; Sasaki, S. Tetrahedron 1997, 53, 3035-3045.
29. Sessler, J. L.; Wang, B.; Harriman, A. J. Am. Chem. Soc. 1995, 117, 704-714.
30. Herrmann, W. A.; Brossmer, C.; Ofele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844-1849.
31. Bobek, M.; Kavai, I.; Sharma, R. A.; Grill, S.; Dutschman, G.; Cheng, Y.-C. J. Med. Chem. 1987, 30, 2154-2157.
32. Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1993, 115, 905-916.
33. For review in the utilization of mass spectrometry for characterization of supramolecular aggregates, see: Schalley, C. A. Mass. Spectrom. Rev. 2001, 20, 253-309.
34. Nonspecific higher order aggragegation in ESI may generate small ions between 1600 and 1700 TH in the top spectrum of Figure 3.
35. Control 3 was specifically chosen because, by protecting the exocyclic amine with an isobutyrylamide group, there is the possibility of forming an intramolecular hydrogen bond with the carbonyl moeity of the amide and the guanosine imino proton (NH-1). In this conformation, the protecting group not only eliminates the availability of two of the three Watson-Crick H-bonding sites of guanosine but also introduces steric crowding. Thus, it is unlikely that 3 will form Watson-Crick H-bonds in this conformation. However, if the intramolecluar H-bond is disrupted, then control compound 3 could form Watson-Crick H-bonds (using the amide NH as an alternative to the regular amino NH of guanosine) and hence possibly form a cyclic trimer. However, all the solution-phase studies are consistent with 3 being present as a monomer. In addition, it has been previously shown that the use of this protecting group serves to block Watson-Crick hydrogen bonding interactions (see: Sessler, J. L. ; Sathiosatham, M.; Brown, C. T.; Rhodes, T. A.; Wiederrecht, G. J. Am. Chem. Soc. 2001, 123, 3655-3660). Thus, the trimeric species observed in the mass spectra most likely reflects nonspecific gas-phase interactions, rather than a discrete ensemble such as I.
36. (a) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 271, 1095-1098.
37. (b) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37-44.
38. Michelson, U.; Hunter, C. A. Angew. Chem., Int. Ed. 2000, 39, 764-767.