Chemical Primer Extension: Individual Steps of Spontaneous Replication
Jan A. Rojas Stütz
Institute for Organic Chemistry, University of Karlsruhe (TH), D-76131 Karlsruhe, (phone: +49-721-6082091; fax: +49-721-6084825)
Search for more papers by this authorEric Kervio
Institute for Organic Chemistry, University of Karlsruhe (TH), D-76131 Karlsruhe, (phone: +49-721-6082091; fax: +49-721-6084825)
Search for more papers by this authorChristopher Deck
Institute for Organic Chemistry, University of Karlsruhe (TH), D-76131 Karlsruhe, (phone: +49-721-6082091; fax: +49-721-6084825)
Search for more papers by this authorClemens Richert
Institute for Organic Chemistry, University of Karlsruhe (TH), D-76131 Karlsruhe, (phone: +49-721-6082091; fax: +49-721-6084825)
Search for more papers by this authorJan A. Rojas Stütz
Institute for Organic Chemistry, University of Karlsruhe (TH), D-76131 Karlsruhe, (phone: +49-721-6082091; fax: +49-721-6084825)
Search for more papers by this authorEric Kervio
Institute for Organic Chemistry, University of Karlsruhe (TH), D-76131 Karlsruhe, (phone: +49-721-6082091; fax: +49-721-6084825)
Search for more papers by this authorChristopher Deck
Institute for Organic Chemistry, University of Karlsruhe (TH), D-76131 Karlsruhe, (phone: +49-721-6082091; fax: +49-721-6084825)
Search for more papers by this authorClemens Richert
Institute for Organic Chemistry, University of Karlsruhe (TH), D-76131 Karlsruhe, (phone: +49-721-6082091; fax: +49-721-6084825)
Search for more papers by this authorAbstract
The replication of genetic information, as we know it from today's biology, relies on template-directed, polymerase-catalyzed extension of primers. It is known that short stretches of complementary RNA can form on templates in the absence of enzymes. This account summarizes recent work on efficient enzyme-free primer extension, both with 3′-amino-terminal deoxyribonucleotide primers and with primers made of unmodified RNA. Near-quantitative primer extension with half-life times on the order of hours has been demonstrated by using azaoxybenzotriazolides of nucleotides and downstream-binding oligomers. Further, small non-nucleosidic substituents placed on the terminus of the template or the downstream-binding oligomer have been shown to increase the rate and fidelity of primer-extension reactions. Since all four templating bases (A, C, G, T/U) direct sequence-selective primer-extension steps, we feel that there is renewed hope that full, nonenzymatic replication from monomers may eventually be achieved.
References
- 1 R. Naylor, P. T. Gilham, Biochemistry 1966, 5, 2722.
- 2 A. Luther, R. Brandsch, G. von Kiedrowski, Nature 1998, 396, 245.
- 3a L. E. Orgel, Crit. Rev. Biochem. Mol. Biol. 2004, 39, 99;
- 3b I. A. Kozlov, L. E. Orgel, Mol. Biol. 2000, 34, 781.
- 4 S. Pitsch, A. Eschenmoser, B. Degulin, S. Hui, G. Arrhenius, Origins Life Evol. Biosphere 1995, 25, 297.
- 5 T. Haertle, L. E. Orgel, J. Mol. Biol. 1986, 188, 77.
- 6 Z. Y. Zhan, D. G. Lynn, J. Am. Chem. Soc. 1997, 119, 12420.
- 7 J. Sulston, R. Lohrmann, L. E. Orgel, H. T. Miles, Prod. Natl. Acad. Sci. U.S.A. 1968, 59, 726.
- 8 T. Wu, L. E. Orgel, J. Am. Chem. Soc. 1992, 114, 7963.
- 9 G. F. Joyce, L. E. Orgel, J. Mol. Biol. 1988, 202, 677.
- 10 M. Hey, C. Hartel, M. W. Göbel, Helv. Chim. Acta 2003, 86, 844.
- 11 T. Wu, L. E. Orgel, J. Am. Chem. Soc. 1992, 114, 317.
- 12 I. A. Kozlov, S. Pitsch, L. E. Orgel, Proc. Natl. Acad. Sci. U.S.A 1998, 95, 13448.
- 13 A. Kanavarioti, M. W. Stronach, R. J. Ketner, T. B. Hurley, J. Org. Chem. 1995, 60, 623.
- 14 W. S. Zielinski, L. E. Orgel, Nature 1987, 327, 346.
- 15 W. S. Zielinski, L. E. Orgel, Nucleic Acids Res. 1987, 15, 1699.
- 16 N. Griesang, K. Giessler, T. Lommel, C. Richert, Angew. Chem., Int. Ed. 2006, 45, 6144.
- 17 D. Sarracino, C. Richert, Bioorg. Med. Chem. Lett. 1996, 6, 2543.
- 18 C. F. Bleczinski, C. Richert, J. Am. Chem. Soc. 1999, 121, 10889.
- 19 S. Narayanan, J. Gall, C. Richert, Nucleic Acids Res. 2004, 32, 2901.
- 20 J. Tuma, W. H. Connors, D. H. Stitelman, C. Richert, J. Am. Chem. Soc. 2002, 124, 4236.
- 21 Z. Dogan, R. Paulini, J. A. Rojas Stütz, S. Narayanan, C. Richert, J. Am. Chem. Soc. 2004, 126, 4762.
- 22 L. A. Loeb, T. A. Kunkel, Annu. Rev. Biochem. 1982, 52, 429.
- 23 J. A. Rojas Stütz, C. Richert, J. Am. Chem. Soc. 2001, 123, 12718.
- 24 H. Suga, P. A. Lohse, J. W. Szostak, J. Am. Chem. Soc. 1998, 120, 1151.
- 25 L. E. Orgel, R. Lohrmann, Acc. Chem. Res. 1974, 7, 368.
- 26 B. Oró, J. Basile, S. Cortes, C. Shen, T. Yamron, Origins of Life 1984, 14, 237.
- 27 J. A. Rojas Stütz, Ph.D. Thesis, University of Karlsruhe (TH), Germany, 2004.
- 28 J. A. Rojas Stütz, C. Richert, Chem.–Eur. J. 2006, 12, 2472.
- 29 P. Hagenbuch, E. Kervio, A. Hochgesand, U. Plutowski, C. Richert, Angew. Chem., Int. Ed. 2005, 44, 6588.
- 30 A. Kanavarioti, C. F. Bernasconi, E. E. Baird, J. Am. Chem. Soc. 1998, 120, 8575.
- 31 M. Kurz, K. Göbel, C. Hartel, M. W. Göbel, Helv. Chim. Acta 1998, 81, 1156.
- 32 P. Baumhof, N. Griesang, M. Bächle, C. Richert, J. Org. Chem. 2006, 71, 1060.
- 33 T. Mukaiyama, M. Hashimoto, J. Am. Chem. Soc. 1972, 94, 8528.
- 34 R. Lohrmann, L. E. Orgel, Tetrahedron 1978, 34, 853.
- 35 K. J. Prahabar, T. D. Cole, J. P. Ferris, J. Am. Chem. Soc. 1994, 116, 10914.
- 36
L. A. Carpino, H. Imazumi, A. El-Faham, F. J. Ferrer, C. Zhang, Y. Lee, B. M. Foxman, P. Henklein, C. Hanay, C. Mügge, H. Wenschuh, J. Klose, M. Beyermann, M. Bienert, Angew. Chem., Int. Ed. 2002, 41, 441.
10.1002/1521-3773(20020201)41:3<441::AID-ANIE441>3.0.CO;2-N CAS PubMed Web of Science® Google Scholar
- 37 L. A. Carpino, J. Am. Chem. Soc. 1993, 115, 4397.
- 38 G. van der Marel, C. A. A. van Boeckel, G. Wille, J. H. van Boom, Tetrahedron Lett. 1981, 22, 3887.
- 39 N. Griesang, E. Kervio, C. Richert, Synthesis 2005, 2327.
- 40 S. R. Vogel, C. Deck, C. Richert, Chem. Commun. 2005, 4922.
- 41 S. R. Vogel, Ph.D. Thesis, University of Karlsruhe (TH), Germany, 2006.
- 42 C. Deck, Diploma Thesis, University of Karlsruhe (TH), Germany, 2006.
- 43 T. Inoue, L. E. Orgel, J. Mol. Biol. 1982, 162, 201.
- 44 T. Inoue, L. E. Orgel, J. Am. Chem. Soc. 1981, 103, 7666.
- 45 N. G. Dolinnaya, N. I. Sokolova, D. T. Ashirbekova, Z. A. Shabarova, Nucl. Acids Res. 1991, 19, 3067.
- 46 L. J. McBride, M. H. Caruthers, Tetrahedron Lett. 1983, 24, 245.
- 47 M. H. Caruthers, A. D. Barone, S. L. Beaucage, D. R. Dodds, E. F. Fisher, L. J. McBride, M. Matteucci, Z. Stabinsky, J. Y. Tang, Methods Enzymol. 1987, 154, 287.
