Nonenzymatic Oligomerization of Ribonucleotides on Guanosine-Rich Templates: Suppression of the Self-Pairing of Guanosine

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 8, 1997, Pages 842-845

  Kurz, Markus ^a   Göbel, Karin ^a   Hartel, Christian ^a   Göbel, Michael W ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

Molecular recognition; Oligonucleotides; RNA; Self replication

Indexed keywords

EID: 0031007782     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199708421     Document Type: Article

References (37)

1. Reviews: a) G. F. Joyce in Cold Spring Harbor Symposia on Quantitative Biology, Vol. LII, Cold Spring Harbor Press, Cold Spring Harbor, NY, 1987, pp. 41-51; b) A. Kanavarioti, Origins Life Evol. Biosphere 1994, 24, 479-494; c) L. E. Orgel, Acc. Chem. Res. 1995, 28, 109-118.
2. Reviews: a) G. F. Joyce in Cold Spring Harbor Symposia on Quantitative Biology, Vol. LII, Cold Spring Harbor Press, Cold Spring Harbor, NY, 1987, pp. 41-51; b) A. Kanavarioti, Origins Life Evol. Biosphere 1994, 24, 479-494; c) L. E. Orgel, Acc. Chem. Res. 1995, 28, 109-118.
3. Reviews: a) G. F. Joyce in Cold Spring Harbor Symposia on Quantitative Biology, Vol. LII, Cold Spring Harbor Press, Cold Spring Harbor, NY, 1987, pp. 41-51; b) A. Kanavarioti, Origins Life Evol. Biosphere 1994, 24, 479-494; c) L. E. Orgel, Acc. Chem. Res. 1995, 28, 109-118.
4. a) T. Wu, L. E. Orgel, J. Am. Chem. Soc. 1992, 114, 317-322;
5. b) ibid. 1992, 114, 5496-5501;
6. c) ibid. 1992, 114, 7963-7969;
7. d) A. R. Hill, Jr., L. E. Orgel, T. Wu, Origins Life Evol. Biosphere 1993, 23, 285-290;
8. e) A. Kanavarioti, C. F. Bernasconi, D. J. Alberas, E. E. Baird, J. Am. Chem. Soc. 1993, 115, 8537-8546.
9. Catalysis of the formation of RNA by metal ions: a) H. Sawai, K. Higa, K. Kuroda, J. Chem. Soc. Perkin Trans. 1 1992, 505-508; b) R. Rohatgi, D. P. Bartel, J. W. Szostak, J. Am. Chem. Soc. 1996, 118, 3332-3339; c) ibid. 1996, 118, 3340-3344; by minerals: d) G. Ertem, J. P. Ferris, Nature 1996, 379, 238-240; e) J. P. Ferris, A. R. Hill, R. H. Liu, L. E. Orgel, ibid. 1996, 381. 59-61; by peptides: f) B. Barbier, J. Visscher, A. W. Schwartz, J. Mol. Evol. 1993, 37, 554-558; by ribozymes: g) E. H. Ekland, J. W. Szostak, D. P. Bartel, Science 1995, 269, 373-376; h) E. H. Ekland, D. P. Bartel, Nature 1996, 382, 373-376.
10. Catalysis of the formation of RNA by metal ions: a) H. Sawai, K. Higa, K. Kuroda, J. Chem. Soc. Perkin Trans. 1 1992, 505-508; b) R. Rohatgi, D. P. Bartel, J. W. Szostak, J. Am. Chem. Soc. 1996, 118, 3332-3339; c) ibid. 1996, 118, 3340-3344; by minerals: d) G. Ertem, J. P. Ferris, Nature 1996, 379, 238-240; e) J. P. Ferris, A. R. Hill, R. H. Liu, L. E. Orgel, ibid. 1996, 381. 59-61; by peptides: f) B. Barbier, J. Visscher, A. W. Schwartz, J. Mol. Evol. 1993, 37, 554-558; by ribozymes: g) E. H. Ekland, J. W. Szostak, D. P. Bartel, Science 1995, 269, 373-376; h) E. H. Ekland, D. P. Bartel, Nature 1996, 382, 373-376.
11. Catalysis of the formation of RNA by metal ions: a) H. Sawai, K. Higa, K. Kuroda, J. Chem. Soc. Perkin Trans. 1 1992, 505-508; b) R. Rohatgi, D. P. Bartel, J. W. Szostak, J. Am. Chem. Soc. 1996, 118, 3332-3339; c) ibid. 1996, 118, 3340-3344; by minerals: d) G. Ertem, J. P. Ferris, Nature 1996, 379, 238-240; e) J. P. Ferris, A. R. Hill, R. H. Liu, L. E. Orgel, ibid. 1996, 381. 59-61; by peptides: f) B. Barbier, J. Visscher, A. W. Schwartz, J. Mol. Evol. 1993, 37, 554-558; by ribozymes: g) E. H. Ekland, J. W. Szostak, D. P. Bartel, Science 1995, 269, 373-376; h) E. H. Ekland, D. P. Bartel, Nature 1996, 382, 373-376.
12. Catalysis of the formation of RNA by metal ions: a) H. Sawai, K. Higa, K. Kuroda, J. Chem. Soc. Perkin Trans. 1 1992, 505-508; b) R. Rohatgi, D. P. Bartel, J. W. Szostak, J. Am. Chem. Soc. 1996, 118, 3332-3339; c) ibid. 1996, 118, 3340-3344; by minerals: d) G. Ertem, J. P. Ferris, Nature 1996, 379, 238-240; e) J. P. Ferris, A. R. Hill, R. H. Liu, L. E. Orgel, ibid. 1996, 381. 59-61; by peptides: f) B. Barbier, J. Visscher, A. W. Schwartz, J. Mol. Evol. 1993, 37, 554-558; by ribozymes: g) E. H. Ekland, J. W. Szostak, D. P. Bartel, Science 1995, 269, 373-376; h) E. H. Ekland, D. P. Bartel, Nature 1996, 382, 373-376.
13. Catalysis of the formation of RNA by metal ions: a) H. Sawai, K. Higa, K. Kuroda, J. Chem. Soc. Perkin Trans. 1 1992, 505-508; b) R. Rohatgi, D. P. Bartel, J. W. Szostak, J. Am. Chem. Soc. 1996, 118, 3332-3339; c) ibid. 1996, 118, 3340-3344; by minerals: d) G. Ertem, J. P. Ferris, Nature 1996, 379, 238-240; e) J. P. Ferris, A. R. Hill, R. H. Liu, L. E. Orgel, ibid. 1996, 381. 59-61; by peptides: f) B. Barbier, J. Visscher, A. W. Schwartz, J. Mol. Evol. 1993, 37, 554-558; by ribozymes: g) E. H. Ekland, J. W. Szostak, D. P. Bartel, Science 1995, 269, 373-376; h) E. H. Ekland, D. P. Bartel, Nature 1996, 382, 373-376.
14. Catalysis of the formation of RNA by metal ions: a) H. Sawai, K. Higa, K. Kuroda, J. Chem. Soc. Perkin Trans. 1 1992, 505-508; b) R. Rohatgi, D. P. Bartel, J. W. Szostak, J. Am. Chem. Soc. 1996, 118, 3332-3339; c) ibid. 1996, 118, 3340-3344; by minerals: d) G. Ertem, J. P. Ferris, Nature 1996, 379, 238-240; e) J. P. Ferris, A. R. Hill, R. H. Liu, L. E. Orgel, ibid. 1996, 381. 59-61; by peptides: f) B. Barbier, J. Visscher, A. W. Schwartz, J. Mol. Evol. 1993, 37, 554-558; by ribozymes: g) E. H. Ekland, J. W. Szostak, D. P. Bartel, Science 1995, 269, 373-376; h) E. H. Ekland, D. P. Bartel, Nature 1996, 382, 373-376.
15. Catalysis of the formation of RNA by metal ions: a) H. Sawai, K. Higa, K. Kuroda, J. Chem. Soc. Perkin Trans. 1 1992, 505-508; b) R. Rohatgi, D. P. Bartel, J. W. Szostak, J. Am. Chem. Soc. 1996, 118, 3332-3339; c) ibid. 1996, 118, 3340-3344; by minerals: d) G. Ertem, J. P. Ferris, Nature 1996, 379, 238-240; e) J. P. Ferris, A. R. Hill, R. H. Liu, L. E. Orgel, ibid. 1996, 381. 59-61; by peptides: f) B. Barbier, J. Visscher, A. W. Schwartz, J. Mol. Evol. 1993, 37, 554-558; by ribozymes: g) E. H. Ekland, J. W. Szostak, D. P. Bartel, Science 1995, 269, 373-376; h) E. H. Ekland, D. P. Bartel, Nature 1996, 382, 373-376.
16. Catalysis of the formation of RNA by metal ions: a) H. Sawai, K. Higa, K. Kuroda, J. Chem. Soc. Perkin Trans. 1 1992, 505-508; b) R. Rohatgi, D. P. Bartel, J. W. Szostak, J. Am. Chem. Soc. 1996, 118, 3332-3339; c) ibid. 1996, 118, 3340-3344; by minerals: d) G. Ertem, J. P. Ferris, Nature 1996, 379, 238-240; e) J. P. Ferris, A. R. Hill, R. H. Liu, L. E. Orgel, ibid. 1996, 381. 59-61; by peptides: f) B. Barbier, J. Visscher, A. W. Schwartz, J. Mol. Evol. 1993, 37, 554-558; by ribozymes: g) E. H. Ekland, J. W. Szostak, D. P. Bartel, Science 1995, 269, 373-376; h) E. H. Ekland, D. P. Bartel, Nature 1996, 382, 373-376.
17. Self-replicating oligonucleotides: a) G. von Kiedrowski, Angew. Chem. 1986, 98, 932-934; Angew. Chem. Int. Ed. Engl. 1986, 25, 932-935; b) G. von Kiedrowski, B. Wlotzka, J. Helbing, ibid. 1989, 101, 1259-1261 and 1989, 28, 1235-1237; c) G. von Kiedrowski, B. Wlotzka, J. Helbing, M. Matzen, S. Jordan, ibid. 1991, 103, 456-459, 1066 and 1991, 30, 423-426, 892; d) D. Sievers, G. von Kiedrowski, Nature 1994, 369, 221-224; e) T. Li, K. C. Nicolaou, ibid. 1994, 369, 218-221.
18. Self-replicating oligonucleotides: a) G. von Kiedrowski, Angew. Chem. 1986, 98, 932-934; Angew. Chem. Int. Ed. Engl. 1986, 25, 932-935; b) G. von Kiedrowski, B. Wlotzka, J. Helbing, ibid. 1989, 101, 1259-1261 and 1989, 28, 1235-1237; c) G. von Kiedrowski, B. Wlotzka, J. Helbing, M. Matzen, S. Jordan, ibid. 1991, 103, 456-459, 1066 and 1991, 30, 423-426, 892; d) D. Sievers, G. von Kiedrowski, Nature 1994, 369, 221-224; e) T. Li, K. C. Nicolaou, ibid. 1994, 369, 218-221.
19. Self-replicating oligonucleotides: a) G. von Kiedrowski, Angew. Chem. 1986, 98, 932-934; Angew. Chem. Int. Ed. Engl. 1986, 25, 932-935; b) G. von Kiedrowski, B. Wlotzka, J. Helbing, ibid. 1989, 101, 1259-1261 and 1989, 28, 1235-1237; c) G. von Kiedrowski, B. Wlotzka, J. Helbing, M. Matzen, S. Jordan, ibid. 1991, 103, 456-459, 1066 and 1991, 30, 423-426, 892; d) D. Sievers, G. von Kiedrowski, Nature 1994, 369, 221-224; e) T. Li, K. C. Nicolaou, ibid. 1994, 369, 218-221.
20. Self-replicating oligonucleotides: a) G. von Kiedrowski, Angew. Chem. 1986, 98, 932-934; Angew. Chem. Int. Ed. Engl. 1986, 25, 932-935; b) G. von Kiedrowski, B. Wlotzka, J. Helbing, ibid. 1989, 101, 1259-1261 and 1989, 28, 1235-1237; c) G. von Kiedrowski, B. Wlotzka, J. Helbing, M. Matzen, S. Jordan, ibid. 1991, 103, 456-459, 1066 and 1991, 30, 423-426, 892; d) D. Sievers, G. von Kiedrowski, Nature 1994, 369, 221-224; e) T. Li, K. C. Nicolaou, ibid. 1994, 369, 218-221.
21. Self-replicating oligonucleotides: a) G. von Kiedrowski, Angew. Chem. 1986, 98, 932-934; Angew. Chem. Int. Ed. Engl. 1986, 25, 932-935; b) G. von Kiedrowski, B. Wlotzka, J. Helbing, ibid. 1989, 101, 1259-1261 and 1989, 28, 1235-1237; c) G. von Kiedrowski, B. Wlotzka, J. Helbing, M. Matzen, S. Jordan, ibid. 1991, 103, 456-459, 1066 and 1991, 30, 423-426, 892; d) D. Sievers, G. von Kiedrowski, Nature 1994, 369, 221-224; e) T. Li, K. C. Nicolaou, ibid. 1994, 369, 218-221.
22. Self-replicating oligonucleotides: a) G. von Kiedrowski, Angew. Chem. 1986, 98, 932-934; Angew. Chem. Int. Ed. Engl. 1986, 25, 932-935; b) G. von Kiedrowski, B. Wlotzka, J. Helbing, ibid. 1989, 101, 1259-1261 and 1989, 28, 1235-1237; c) G. von Kiedrowski, B. Wlotzka, J. Helbing, M. Matzen, S. Jordan, ibid. 1991, 103, 456-459, 1066 and 1991, 30, 423-426, 892; d) D. Sievers, G. von Kiedrowski, Nature 1994, 369, 221-224; e) T. Li, K. C. Nicolaou, ibid. 1994, 369, 218-221.
23. Self-replicating oligonucleotides: a) G. von Kiedrowski, Angew. Chem. 1986, 98, 932-934; Angew. Chem. Int. Ed. Engl. 1986, 25, 932-935; b) G. von Kiedrowski, B. Wlotzka, J. Helbing, ibid. 1989, 101, 1259-1261 and 1989, 28, 1235-1237; c) G. von Kiedrowski, B. Wlotzka, J. Helbing, M. Matzen, S. Jordan, ibid. 1991, 103, 456-459, 1066 and 1991, 30, 423-426, 892; d) D. Sievers, G. von Kiedrowski, Nature 1994, 369, 221-224; e) T. Li, K. C. Nicolaou, ibid. 1994, 369, 218-221.
24. Self-replicating oligonucleotides: a) G. von Kiedrowski, Angew. Chem. 1986, 98, 932-934; Angew. Chem. Int. Ed. Engl. 1986, 25, 932-935; b) G. von Kiedrowski, B. Wlotzka, J. Helbing, ibid. 1989, 101, 1259-1261 and 1989, 28, 1235-1237; c) G. von Kiedrowski, B. Wlotzka, J. Helbing, M. Matzen, S. Jordan, ibid. 1991, 103, 456-459, 1066 and 1991, 30, 423-426, 892; d) D. Sievers, G. von Kiedrowski, Nature 1994, 369, 221-224; e) T. Li, K. C. Nicolaou, ibid. 1994, 369, 218-221.
25. Self-replicating, non-nucleic acid based systems: a) A. Terfort, G. von Kiedrowski, Angew. Chem. 1992, 104, 626-628; Angew. Chem. Int. Ed. Engl. 1992, 31, 654-656; b) E. A. Wintner, B. Tsao, J. Rebek, Jr., J. Org. Chem. 1995, 60, 7997-8001; c) D. N. Reinhoudt, D. M. Rudkevich, F. de Jong, J. Am. Chem. Soc. 1996, 118, 6880-6889; d) R. Wick, P. Walde, P. L. Luisi, ibid. 1995, 117, 1435-1436.
26. Self-replicating, non-nucleic acid based systems: a) A. Terfort, G. von Kiedrowski, Angew. Chem. 1992, 104, 626-628; Angew. Chem. Int. Ed. Engl. 1992, 31, 654-656; b) E. A. Wintner, B. Tsao, J. Rebek, Jr., J. Org. Chem. 1995, 60, 7997-8001; c) D. N. Reinhoudt, D. M. Rudkevich, F. de Jong, J. Am. Chem. Soc. 1996, 118, 6880-6889; d) R. Wick, P. Walde, P. L. Luisi, ibid. 1995, 117, 1435-1436.
27. Self-replicating, non-nucleic acid based systems: a) A. Terfort, G. von Kiedrowski, Angew. Chem. 1992, 104, 626-628; Angew. Chem. Int. Ed. Engl. 1992, 31, 654-656; b) E. A. Wintner, B. Tsao, J. Rebek, Jr., J. Org. Chem. 1995, 60, 7997-8001; c) D. N. Reinhoudt, D. M. Rudkevich, F. de Jong, J. Am. Chem. Soc. 1996, 118, 6880-6889; d) R. Wick, P. Walde, P. L. Luisi, ibid. 1995, 117, 1435-1436.
28. Self-replicating, non-nucleic acid based systems: a) A. Terfort, G. von Kiedrowski, Angew. Chem. 1992, 104, 626-628; Angew. Chem. Int. Ed. Engl. 1992, 31, 654-656; b) E. A. Wintner, B. Tsao, J. Rebek, Jr., J. Org. Chem. 1995, 60, 7997-8001; c) D. N. Reinhoudt, D. M. Rudkevich, F. de Jong, J. Am. Chem. Soc. 1996, 118, 6880-6889; d) R. Wick, P. Walde, P. L. Luisi, ibid. 1995, 117, 1435-1436.
29. Self-replicating, non-nucleic acid based systems: a) A. Terfort, G. von Kiedrowski, Angew. Chem. 1992, 104, 626-628; Angew. Chem. Int. Ed. Engl. 1992, 31, 654-656; b) E. A. Wintner, B. Tsao, J. Rebek, Jr., J. Org. Chem. 1995, 60, 7997-8001; c) D. N. Reinhoudt, D. M. Rudkevich, F. de Jong, J. Am. Chem. Soc. 1996, 118, 6880-6889; d) R. Wick, P. Walde, P. L. Luisi, ibid. 1995, 117, 1435-1436.
30. In an experimental approach to find an answer to the question why nature had preferred RNA and DNA over other plausible alternatives. Eschenmoser and colleagues investigated "pyranosyl-RNA". In this structure type, the phenomenon of guanosine self-association does not occur, thus making it an excellent substrate for template-directed ligation and replication reactions: 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.
31. H. Reinbold, R. K. Robins, F. Seela, L. E. Orgel, J. Mol. Evol. 1994, 38, 211-214.
32. H. Reinbold, L. E. Orgel, J. Mol. Evol. 1994, 38, 205-210.
33. K. Schütz, M. Kurz, M. W. Göbel, Tetrahedron Lett. 1995, 36, 8407-8410.
34. Since the products are completely degraded by ribonucleaseT1 to the phosphorylated primer, in accordance with the finding of Orgel et al. the first ribonucleotide must be bound through the 3′-hydroxy group of the primer (see also Scheme 1 top).
35. D. M. Gray, S.-H. Hung, K. H. Johnson, Methods Enzymol. 1995, 246, 19-71.
36. a) P. Balagurumoorthy, S. K. Brahmachari, D. Mohanty, M. Bansal, V. Sasisekharan, Nucl. Acids Res. 1992, 20, 4061-4067;
37. b) M. Lu, Q. Guo, N. R. Kallenbach, Biochemistry 1993, 32, 598-601.