Nonenzymatic oligomerization of RNA by TNA templates

Organic Letters

Volumn 8, Issue 25, 2006, Pages 5809-5811

  Heuberger, Benjamin O ^a   Switzer, Christopher ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOSINE; ERYTHROSE; GUANOSINE PHOSPHATE; NUCLEIC ACID; RIBONUCLEASE; RNA; TETROSE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; CONFORMATION;

5'-GUANYLIC ACID; CYTOSINE; MODELS, CHEMICAL; NUCLEIC ACID CONFORMATION; NUCLEIC ACIDS; RIBONUCLEASES; RNA; TETROSES;

EID: 33846280487     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062368s     Document Type: Article

References (38)

1. (a) Ricardo, A.; Carrigan, M. A.; Olcott, A. N.; Benner, S. A. Science 2004, 303, 196.
2. (b) Springsteen, G.; Joyce, G. F. J. Am. Chem. Soc. 2004, 126, 9578.
3. (c) Müller, D.; Pitsch, S.; Kittaka, A.; Wagner, E.; Wintner, C. E.; Eschenmoser, A. Helv. Chim. Acta 1990, 73, 1410.
4. Joyce, G. F. Nature 2002, 418, 214.
5. (a) Schöning, K.-U.; Scholz, P.; Guntha, S.; Wu, X.; Krishnamurthy, R.; Eschenmoser, A. Science 2000, 290, 1347.
6. (b) Schöning, K.-U.; Scholz, P.; Wu, X. L.; Guntha, S.; Delgado, G.; Krishnamurthy, R.; Eschenmoser, A. Helv. Chim. Acta 2002, 85, 4111.
7. (c) Pallan, P. S.; Wilds, C. J.; Wawrzak, Z.; Krishnamurthy, R.; Eschenmoser, A.; Egli, M. Angew. Chem., Int. Ed. 2003, 42, 5893.
8. Pitsch, S.; Eschenmoser, A.; Gedulin, B.; Hui, S.; Arrhenius, G. Origins Life Evol. Biosphere 1995, 25, 297.
9. Herdewijn, P. Angew. Chem., Int. Ed. 2001, 40, 2249.
10. For past work exploring nonenzymatic oligomerization on natural nucleotide templates, see: (a) Inoue, T.; Orgel, L. E. J. Am. Chem. Soc. 1981, 103, 7666.
11. (b) Joyce, G. F.; Visser, G. M.; VanBoeckel, C. A. A.; VanBoom, J. H.; Orgel, L. E.; VanWestrenen, J. Nature 1984, 310, 602.
12. (c) Chen, C. B.; Inoue, T.; Orgel, L. E. J. Mol. Biol. 1985, 181, 271.
13. (d) Joyce, G. F.; Orgel, L. E. J. Mol. Biol. 1986, 188, 433.
14. (e) Acevedo, O. L.; Orgel, L. E. J. Mol. Biol. 1987, 197, 187.
15. (f) Wu, T. F.; Orgel, L. E. J. Am. Chem. Soc. 1992, 114, 317.
16. (g) Hill, A. R., Jr.; Orgel, L. E.; Wu, T. F. Origins Life Evol. Biosphere 1993, 23, 285.
17. (h) Zielinski, M.; Kozlov, I. A.; Orgel, L. E. Helv. Chim. Acta 2000, 83, 1678.
18. (i) Kanavarioti, A.; Bernasconi, C. F.; Baird, E. E. J. Am. Chem. Soc. 1998, 120, 8575.
19. (j) Kanavarioti, A.; Baird, E. E.; Hurley, T. B.; Carruthers, J. A.; Gangopadhyay, S. J. Org. Chem. 1999, 64, 8323.
20. (k) Kurz, M.; Gobel, K.; Hartel, C.; Gobel, M. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 842.
21. (l) Hey, M.; Hartel, C.; Gobel, M. W. Helv. Chim. Acta 2003, 86, 844.
22. For past work exploring nonenzymatic oligomerization on nonstandard nucleotide templates, see: (a) Rembold, H.; Robins, R. K.; Seela, F.; Orgel, L. E. J. Mol. Evol. 1994, 38, 211.
23. (b) Bohler, C.; Nielsen, P. E.; Orgel, L. E. Nature 1995, 376, 578.
24. (c) Ertem, G.; Ferris, J. P. Nature 1996, 379, 238.
25. (d) Prakash, T. P.; Roberts, C.; Switzer, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 1522.
26. (e) Kozlov, I. A.; Politis, P. K.; Pitsch, S.; Herdewijn, P.; Orgel, L. E. J. Am. Chem. Soc. 1999, 121, 1108.
27. (f) Kozlov, I. A.; Orgel, L. E. Helv. Chim. Acta 1999, 82, 1799.
28. (g) Chaput, J. C.; Switzer, C. J. Am. Chem. Soc. 2000, 122, 12866.
29. (h) Chaput, J. C.; Switzer, C. J. Mol. Evol. 2000, 51, 464.
30. (i) Kozlov, I. A.; Zielinski, M.; Allart, B.; Kerremans, L.; Van Aerschot, A.; Busson, R.; Herdewijn, P.; Orgel, L. E. Chem.-Eur. J. 2000, 6, 151.
31. (j) Hartel, C.; Gobel, M. W. Helv. Chim. Acta 2000, 83, 2541.
32. (k) Chaput, J. C.; Sinha, S.; Switzer, C. Chem. Commun. 2002, 15, 1568.
33. Cairns-Smith, A. G. Genetic Takeover and the Mineral Origins of Life; Cambridge University Press: Cambridge, 1982.
34. 3b Templates were synthesized on an ABI 394 DNA synthesizer using standard protocols. Guanosine 5′-phosphoro-2-methyl-imidazolide was prepared from guanosine 5′-monophosphate according to the reported procedure: Joyce, G. F.; Inoue, T.; Orgel, L. E. J. Mol. Biol. 1984, 176, 279.
35. Morcillo, J.; Gallego, E.; Peral, F. J. Mol. Struct. 1987, 157, 353.
36. Nelson, K. E.; Levy, M.; Miller, S. L. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 3868.
37. Schmidt, J. G.; Nielsen, P. E.; Orgel, L. E. Nucl. Acids Res. 1997, 25, 4797.
38. 3b