Pyranosyl-RNA Also Forms Hairpin Structures

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 8, 1997, Pages 870-873

  Micura, Ronald ^a   Bolli, Martin ^a   Windhab, Norbert ^b   Eschenmoser, Albert ^a  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY HOSPITAL FRANKFURT   (Germany)

Author keywords

Base pairing; Oligonucleotides; RNA

Indexed keywords

EID: 0030982329     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199708701     Document Type: Article

References (38)

1. M. Bolli, R. Micura, M. Ramaseshan, S. Pitsch, A. Eschenmoser, Helv. Chim. Acta 1997, 80, in press.
2. K. Kruger, P. J. Grabowski, A. J. Zaug, J. Sands, D. E. Gottschling, T. R. Cech, Cell 1982, 31, 147-157; P. Sharp, Angew. Chem. 1994, 106, 1292-1304; Angew. Chem. Int. Ed. Engl. 1994, 33, 1229-1240.
3. K. Kruger, P. J. Grabowski, A. J. Zaug, J. Sands, D. E. Gottschling, T. R. Cech, Cell 1982, 31, 147-157; P. Sharp, Angew. Chem. 1994, 106, 1292-1304; Angew. Chem. Int. Ed. Engl. 1994, 33, 1229-1240.
4. K. Kruger, P. J. Grabowski, A. J. Zaug, J. Sands, D. E. Gottschling, T. R. Cech, Cell 1982, 31, 147-157; P. Sharp, Angew. Chem. 1994, 106, 1292-1304; Angew. Chem. Int. Ed. Engl. 1994, 33, 1229-1240.
5. C. Guerrier-Takada, K. Gardiner, T. Marsh, N. Pace, S. Altman, Cell 1983, 35, 849-857.
6. The concept that an RNA molecule can function as a genotype and at the same type fulfill phenotypic functions appears to have been considered for the first time by S. Spiegelmann in connection with his in vitro evolution experiments on Qb-RNA in the presence of Qb-replicase: D. R. Mills, R. L. Peterson, S. Spiegelman, Proc. Natl. Acacl. Sci. USA 1967, 58, 217-224; D. R. Mills, F. R. Kramer, S. Spiegelman, Science 1973, 180, 916-927; G. Quinkert, H. Bang, D. Reichert, Helv. Chim. Acta 1996, 79, 1260-1278.
7. The concept that an RNA molecule can function as a genotype and at the same type fulfill phenotypic functions appears to have been considered for the first time by S. Spiegelmann in connection with his in vitro evolution experiments on Qb-RNA in the presence of Qb-replicase: D. R. Mills, R. L. Peterson, S. Spiegelman, Proc. Natl. Acacl. Sci. USA 1967, 58, 217-224; D. R. Mills, F. R. Kramer, S. Spiegelman, Science 1973, 180, 916-927; G. Quinkert, H. Bang, D. Reichert, Helv. Chim. Acta 1996, 79, 1260-1278.
8. The concept that an RNA molecule can function as a genotype and at the same type fulfill phenotypic functions appears to have been considered for the first time by S. Spiegelmann in connection with his in vitro evolution experiments on Qb-RNA in the presence of Qb-replicase: D. R. Mills, R. L. Peterson, S. Spiegelman, Proc. Natl. Acacl. Sci. USA 1967, 58, 217-224; D. R. Mills, F. R. Kramer, S. Spiegelman, Science 1973, 180, 916-927; G. Quinkert, H. Bang, D. Reichert, Helv. Chim. Acta 1996, 79, 1260-1278.
9. W. Gilbert, Nature 1986, 319, 618; G. F. Joyce, L. E. Orgel in The RNA World (Eds.: R. F. Gesteland, J. F. Atkins), Cold Spring Harbor Laboratory Press, 1993, pp. 1-25.
10. W. Gilbert, Nature 1986, 319, 618; G. F. Joyce, L. E. Orgel in The RNA World (Eds.: R. F. Gesteland, J. F. Atkins), Cold Spring Harbor Laboratory Press, 1993, pp. 1-25.
11. A. Eschenmoser, M. Dobler, Helv. Chim. Acta 1992, 75, 218-259; "Toward a Chemical Etiology of the Natural Nucleic Acids' Structure": A. Eschenmoser in the Proceedings of the conference 'The R. A. Welch Foundation, 37th Conference on Chemical Research, 40 Years of the DNA Double Helix', R. A. Welch Foundation, Houston TX 1993, 201-235; A. Eschenmoser, E. Loewenthal, Chem. Soc. Rev. 1992, 21, 1-16.
12. A. Eschenmoser, M. Dobler, Helv. Chim. Acta 1992, 75, 218-259; "Toward a Chemical Etiology of the Natural Nucleic Acids' Structure": A. Eschenmoser in the Proceedings of the conference 'The R. A. Welch Foundation, 37th Conference on Chemical Research, 40 Years of the DNA Double Helix', R. A. Welch Foundation, Houston TX 1993, 201-235; A. Eschenmoser, E. Loewenthal, Chem. Soc. Rev. 1992, 21, 1-16.
13. A. Eschenmoser, M. Dobler, Helv. Chim. Acta 1992, 75, 218-259; "Toward a Chemical Etiology of the Natural Nucleic Acids' Structure": A. Eschenmoser in the Proceedings of the conference 'The R. A. Welch Foundation, 37th Conference on Chemical Research, 40 Years of the DNA Double Helix', R. A. Welch Foundation, Houston TX 1993, 201-235; A. Eschenmoser, E. Loewenthal, Chem. Soc. Rev. 1992, 21, 1-16.
14. A. Eschenmoser in Mensch und Natur, special issue on the 250th anniversary of the Naturforschenden Gesellschaft in Zürich 1746-1996 (Eds.: Redaktion-skommission der NGZ), Koprint AG, Alpnach Dorf, 1996, pp. 62-72; English version: A. Eschenmoser, M. V. Kisakürek, Helv. Chim. Acta 1996, 79, 1249-1259.
15. A. Eschenmoser in Mensch und Natur, special issue on the 250th anniversary of the Naturforschenden Gesellschaft in Zürich 1746-1996 (Eds.: Redaktion-skommission der NGZ), Koprint AG, Alpnach Dorf, 1996, pp. 62-72; English version: A. Eschenmoser, M. V. Kisakürek, Helv. Chim. Acta 1996, 79, 1249-1259.
16. S. Pitsch, S. Wendeborn, B. Jaun, A. Eschenmoser, Helv. Chim. Acta 1993, 76, 2161-2183.
17. S. Pitsch, R. Krishnamurthy, M. Bolli, S. Wendeborn, A. Holzner, M. Minton, C. Lesueur, I. Schlönvogt, B. Jaun, A. Eschenmoser, Helv. Chim. Acta 1995, 78, 1621-1635.
18. I. Schlönvogt, S. Pitsch, C. Lesueur, A. Eschenmoser, B. Jaun R. M. Wolf, Helv. Chim. Acta 1996, 79, 2316-2345.
19. R. Krishnamurthy, S. Pitsch, M. Minton, C. Miculka, N. Windhab, A. Eschenmoser, Angew. Chem. 1996, 108, 1619-1623; Angew. Chem. Int. Ed. Engl. 1996, 35, 1537-1541.
20. R. Krishnamurthy, S. Pitsch, M. Minton, C. Miculka, N. Windhab, A. Eschenmoser, Angew. Chem. 1996, 108, 1619-1623; Angew. Chem. Int. Ed. Engl. 1996, 35, 1537-1541.
21. For the structural analysis of a p-RNA duplex by NMR spectroscopy, see [10].
22. See also the studies on enzymatic in vitro evolution of RNA: M. Eigen, W. Gardiner, Pure Appl. Chem. 1984, 56, 967-978; A. D. Ellington, J. W. Szostak, Nature 1990, 346, 818-822; A. A. Beaudry, G. F. Joyce, Science 1992, 257, 635-641; M. Famulok, J. Am. Chem. Soc. 1994, 116, 1698-1706.
23. See also the studies on enzymatic in vitro evolution of RNA: M. Eigen, W. Gardiner, Pure Appl. Chem. 1984, 56, 967-978; A. D. Ellington, J. W. Szostak, Nature 1990, 346, 818-822; A. A. Beaudry, G. F. Joyce, Science 1992, 257, 635-641; M. Famulok, J. Am. Chem. Soc. 1994, 116, 1698-1706.
24. See also the studies on enzymatic in vitro evolution of RNA: M. Eigen, W. Gardiner, Pure Appl. Chem. 1984, 56, 967-978; A. D. Ellington, J. W. Szostak, Nature 1990, 346, 818-822; A. A. Beaudry, G. F. Joyce, Science 1992, 257, 635-641; M. Famulok, J. Am. Chem. Soc. 1994, 116, 1698-1706.
25. See also the studies on enzymatic in vitro evolution of RNA: M. Eigen, W. Gardiner, Pure Appl. Chem. 1984, 56, 967-978; A. D. Ellington, J. W. Szostak, Nature 1990, 346, 818-822; A. A. Beaudry, G. F. Joyce, Science 1992, 257, 635-641; M. Famulok, J. Am. Chem. Soc. 1994, 116, 1698-1706.
26. S. Pitsch, S. Wendeborn, R. Krishnamurthy, M. Bolli, M. Minton, A. Holzner, C. Miculka, N. Windhab, A. Eschenmoser, Helv. Chim. Acta 1997, 80, submitted.
27. U. Pieles, W. Zürcher, M. Schär, H. E. Moser, Nucleic Acids Res. 1993, 21, 3191-3196.
28. L. Marky, K. Breslauer, Biopolymers 1987, 26, 1601-1620.
29. For the characterization and structural elucidation of synthetic hairpin oligonucleotide sequences in the RNA and DNA series, see P. W. Davis, W. Thurmes, I. Tinoco, Jr., Nucleic Acids Res. 1993, 21, 537-545; D. R. Groebe, O. C. Uhlenbeck, ibid. 1988, 15, 11725-11735; C. W. Hilbers, C. A. G. Haasnoot, S. H. de Bruin, J. J. M. Joodens, G. A. van der Marel, J. H. van Boom, Biochimie 1985, 67, 685-695.
30. For the characterization and structural elucidation of synthetic hairpin oligonucleotide sequences in the RNA and DNA series, see P. W. Davis, W. Thurmes, I. Tinoco, Jr., Nucleic Acids Res. 1993, 21, 537-545; D. R. Groebe, O. C. Uhlenbeck, ibid. 1988, 15, 11725-11735; C. W. Hilbers, C. A. G. Haasnoot, S. H. de Bruin, J. J. M. Joodens, G. A. van der Marel, J. H. van Boom, Biochimie 1985, 67, 685-695.
31. For the characterization and structural elucidation of synthetic hairpin oligonucleotide sequences in the RNA and DNA series, see P. W. Davis, W. Thurmes, I. Tinoco, Jr., Nucleic Acids Res. 1993, 21, 537-545; D. R. Groebe, O. C. Uhlenbeck, ibid. 1988, 15, 11725-11735; C. W. Hilbers, C. A. G. Haasnoot, S. H. de Bruin, J. J. M. Joodens, G. A. van der Marel, J. H. van Boom, Biochimie 1985, 67, 685-695.
32. J. Hunziker, H.-J. Roth, M. Böhringer, A. Giger, U. Diederichsen, M. Göbel, R. Krishnan, B. Jaun, C. Leumann, A. Eschenmoser, Helv. Chim. Acta 1993, 76, 259-352 (see therein p. 331, Figure 31).
33. M. Egli, P. Lubini, M. Bolli, S. Pitsch, A. Eschenmoser, unpublished results.
34. M. Bolli, R. Micura, A. Eschenmoser, Chem. Biol., submitted.
35. These stability differences in p-RNA duplexes are particularly pronounced for pyrimidine-purine (relative to purine-pyrimidine) block sequences. For sequences with alternating bases the differences are smaller: however, no exceptions in the trend have yet been observed.
36. M. Petersheim, D. H. Turner, Biochem. 1983, 22, 256-263; S. M. Freier, B. J. Burger, D. Alkema, T. Neilson, D. H. Turner, ibid. 1983, 22, 6198-6206; M. Senior, R. A. Jones, K. J. Breslauer, ibid. 1988, 27, 3879-3885.
37. M. Petersheim, D. H. Turner, Biochem. 1983, 22, 256-263; S. M. Freier, B. J. Burger, D. Alkema, T. Neilson, D. H. Turner, ibid. 1983, 22, 6198-6206; M. Senior, R. A. Jones, K. J. Breslauer, ibid. 1988, 27, 3879-3885.
38. M. Petersheim, D. H. Turner, Biochem. 1983, 22, 256-263; S. M. Freier, B. J. Burger, D. Alkema, T. Neilson, D. H. Turner, ibid. 1983, 22, 6198-6206; M. Senior, R. A. Jones, K. J. Breslauer, ibid. 1988, 27, 3879-3885.