The Disclosure of the Stepwise Supramolecular Organization of Guanosine Derivatives: Serendipity or Programmed Design?

Gian Piero Spada; Giovanni Gottarelli

doi:10.1055/s-2004-817747

ACCOUNT

The Disclosure of the Stepwise Supramolecular Organization of Guanosine Derivatives: Serendipity or Programmed Design?

Gian Piero Spada, Giovanni Gottarelli*
Dipartimento di Chimica Organica ‘A. Mangini’, Alma Mater Studiorum - Università di Bologna, Via San Donato 15, 40127 Bologna, Italy
e-Mail: Giovanni.Gottarelli@unibo.it; e-Mail: GianPiero.Spada@unibo.it;

Abstract

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Abstract

The discovery of several supramolecular architectures generated by guanosine derivatives is described. The story started at the end of the ’80s from the fortuitous observation of a lyotropic behavior exhibited by a guanylic nucleotide in water. This observation stimulated extensive research on several guanosine derivatives which self-assemble in different architectures (discs, ribbons, helices,.) according to their structure and environment. These ordered structures can be used as scaffolds for photo- or electroactive moieties and for the fabrication of molecular electronic devices.

Key words

guanosine - G-quartet - G-ribbon - G-quadruplex - self-assembly - supramolecular chemistry - current rectifiers

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References

1 Lehn JM. Supramolecular Chemistry - Concepts and Perspectives VCH; Weinheim: 1995.

2 Bonazzi S. Capobianco M. De Morais MM. Garbesi A. Gottarelli G. Mariani P. Ponzi Bossi MG. Spada GP. Tondelli L. J. Am. Chem. Soc. 1991, 113: 5809

3 Bonazzi S. De Morais MM. Gottarelli G. Mariani P. Spada GP. Angew. Chem., Int. Ed. Engl. 1993, 32: 248

4 Ciuchi F. Di Nicola G. Franz H. Gottarelli G. Mariani P. Ponzi Bossi MG. Spada GP. J. Am. Chem. Soc. 1994, 116: 7064

5 Bang I. Biochem. Z. 1910, 26: 293

6 Gellert M. Lipsett MN. Davies DR. Proc. Nat. Acad. Sci. U.S.A. 1962, 48: 1463

7 Gushlbauer W. Chantot JF. Thiele DJ. Biomol. Struct. Dyn. 1990, 8: 491 ; and references therein

8 Zimmermann SB. Cohen GH. Davies DR. J. Mol. Biol. 1975, 92: 181

9 Laughlan G. Murchie AIH. Norman DG. Moore MH. Moody PCE. Lilley DMJ. Luisi B. Science 1994, 265: 520

10 Gilbert DE. Feigon J. Curr. Opin. Struc. Biol. 1999, 9: 305

11 Gottarelli G. Proni G. Spada GP. Liq. Cryst. 1997, 22: 563

12 Gottarelli G. Spada GP. Garbesi A. In Comprehensive Supramolecular Chemistry - Templating Self-assembly and Self-organisation Vol. 9: Sauvage JP. Hosseini MW. Pergamon; Oxford: 1996. p.483

13 Gottarelli G. Masiero S. Spada GP. J. Chem. Soc., Chem. Commun. 1995, 2555

14 Davis JT. Tirumala S. Jenssen J. Radler E. Fabris D. J. Org. Chem. 1995, 60: 4167

15 Smith FW. Feigon J. Nature (London, U.K.) 1992, 356: 164

16 Schultze P. Hud NV. Smith FW. Feigon J. Nucl. Acids Res. 1999, 27: 3018

17 Marlow AL. Mezzina E. Spada GP. Masiero S. Davis JT. Gottarelli G. J. Org. Chem. 1999, 64: 5116

18 Mezzina E. Mariani P. Itri R. Masiero S. Pieraccini S. Spada GP. Spinozzi F. Davis JT. Gottarelli G. Chem.-Eur. J. 2001, 7: 388

19 Forman SL. Fettinger JC. Pieraccini S. Gottarelli G. Davis JT. J. Am. Chem. Soc. 2000, 122: 4060

20 Manet I. Francini L. Masiero S. Pieraccini S. Spada GP. Gottarelli G. Helv. Chim. Acta 2001, 84: 2096

21 Andrisano V. Masiero S. Heijne EH. Pieraccini S. Spada GP. Gottarelli G. Angew. Chem. Int. Ed. 1999, 38: 2386

22 Pieraccini S. Gottarelli G. Mariani P. Masiero S. Saturni L. Spada GP. Chirality 2001, 13: 7

23 Gottarelli G. Masiero S. Mezzina E. Pieraccini S. Rabe JP. Samorì P. Spada GP. Chem.-Eur. J. 2000, 6: 3242

24 Giorgi T. Grepioni F. Manet I. Mariani P. Masiero S. Mezzina E. Pieraccini S. Saturni L. Spada GP. Gottarelli G. Chem.-Eur. J. 2002, 8: 2143

25 Kato T. Science 2002, 295: 2414

26 Araki K. Takasawa R. Yoshikawa I. Chem. Commun. 2001, 1826

27 Sato T. Seko M. Takasawa R. Yoshikawa I. Araki K. J. Mater. Chem. 2001, 11: 3018

28 Rinaldi R. Branca E. Cingolani R. Masiero S. Spada GP. Gottarelli G. Appl. Phys. Lett. 2001, 78: 3541

29 Rinaldi R. Maruccio G. Biasco A. Arima V. Cingolani R. Giorgi T. Masiero S. Spada GP. Gottarelli G. Nanotechnology 2002, 13: 398

30 Maruccio G. Visconti P. Arima V. D’Amico S. Blasco A. D’Amone E. Cingolani R. Rinaldi R. Masiero S. Giorgi T. Gottarelli G. Nanoletters 2003, 3: 479

31 Sessler JL. Sathiosatham M. Doerr K. Lynch V. Abboud KH. Angew. Chem. Int. Ed. 2000, 39: 1300

32 Giorgi T. Lena S. Mariani P. Cremonini MA. Masiero S. Pieraccini S. Rabe JP. Samorì P. Spada GP. Gottarelli G. J. Am. Chem. Soc. 2003, 125: 14741