A small catalytic RNA motif with Diels-Alderase activity

Chemistry and Biology

Volumn 6, Issue 3, 1999, Pages 167-176

  Seelig, Burckhard ^a   Jäschke, Andres ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Cycloaddition; In vitro selection; Oligonucleotide conjugates; Ribozymes; RNA catalysis

Indexed keywords

CATALYSIS; METABOLISM; RNA;

BETULACEAE;

EID: 0033102314     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(99)89008-5     Document Type: Article

References (26)

1. Gold, L., Polisky, B., Uhlenbeck, O. & Yarus, M. (1995). Diversity of oligonucleotide functions. Annu. Rev. Biochem. 64, 763-797.
2. Osborne, S.E. & Ellington, A.D. (1997). Nucleic acid selection and the challenge of combinatorial chemistry. Chem. Rev. 97, 349-370.
3. Robertson, M.P. & Ellington, A.D. (1998). How to make a nucleotide. Nature 395, 223-225.
4. Breaker, R.R. (1997). In vitro selection of catalytic polynucleotides. Chem. Rev. 97, 371-390.
5. Famulok, M. & Jenne, A. (1998). Oligonucleotide libraries - Variatio delectat. Curr. Opin. Chem. Biol. 2, 320-327.
6. Hilvert, D., Hill, K.W., Nared, K.D. & Auditor, M.-T.M. (1989). Antibody catalysis of a Dieis-Alder reaction. J. Am. Chem. Soc. 111, 9261-9262.
7. Gouverneur, V.E., Houk, K.N., de Pascual-Teresa, B., Beno, B., Janda, K.D. & Lerner, R.A. (1993). Control of the exo and endo pathways of the Diels-Alder reaction by antibody catalysis. Science 262, 204-208.
8. Kang, J., Santamaria, J., Hilmersson, G. & Rebek, J.J. (1998). Self-assembled molecular capsule catalyzes a Diels-Alder reaction. J. Am. Chem. Soc. 120, 7389-7390.
9. Morris, K.N., Tarasow, T.M., Julin, C.M, Simons, S.L., Hilvert, D. & Gold, L. (1994). Enrichment for RNA molecules that bind a Diels-Alder transition state analog. Proc. Natl Acad. Sci. USA 91, 13028-13032.
10. Tarasow, T.M., Tarasow, S.L. & Eaton, B.E. (1997). RNA-catalysed carbon-carbon bond formation. Nature 389, 54-57.
11. Seelig, B. & Jäschke, A. (1997). Site-specific modification of enzymatically synthesized RNA: Transcription initiation and Diels-Alder reaction. Tetrahedron Lett. 38, 7729-7732.
12. Seelig, B. & Jäschke, A. (1999). Ternary conjugates of guanosine monophosphate as initiator nucleotides for the enzymatic synthesis of 5′-modified RNAs. Bioconjugate Chem. 10, in press.
13. Rideout, D.C. & Breslow, R. (1980). Hydrophobic acceleration of Diels-Alder reactions. J. Am. Chem. Soc. 102, 7816-7817.
14. Corpet, F. (1988). Multiple sequence alignment with hierarchical clustering. Nucleic Acids Res. 16, 10881-10890.
15. Matzura, O. & Wennborg, A. (1996). RNAdraw: An integrated program for RNA secondary structure calculation and analysis under 32-bit Microsoft Windows. Computer Applications in the Biosciences (CABIOS) 12, 247-249.
16. Jaeger, J.A., Turner, D.H. & Zuker, M. (1989). Improved predictions of secondary structures for RNA. Proc. Natl Acad. Sci. USA 86, 7706-7710.
17. Walter, A.E., et al., & Zuker, M. (1994). Coaxial stacking of helixes enhances binding of oligoribonucleotides and improves predictions of RNA folding. Proc. Natl Acad. Sci. USA 91, 9218-9222.
18. Wilson, C., Nix, J. & Szostak, J.W. (1998). Functional requirements for specific ligand recognition by a biotin-binding RNA pseudoknot. Biochemistry 37, 14410-14419.
19. Chowrira, B.M., Berzal-Herranz, A. & Burke, J.M. (1993). Ionic requirements for RNA binding, cleavage and ligation by the hairpin ribozyme. Biochemistry 32, 1088-1095.
20. Jiang, F., Kumar, R.A., Jones, R.A. & Patel, D.J. (1996). Structural basis of RNA folding and recognition in an AMP-RNA aptamer complex. Nature 382, 183-186.
21. Ferris, J.P., Hill, A., Jr., Liu, R. & Orgel, L.E. (1996). Synthesis of long prebiotic oligomers on mineral surfaces. Nature 381, 59-61.
22. Unrau, P.J. & Bartel, D.P. (1998). RNA-catalyzed nucleotide synthesis. Nature 395, 260-263.
23. Wiegand, T.W., Janssen, R.C. & Eaton, B.E. (1997). Selection of RNA amide synthases. Chem. Biol. 4, 675-683.
24. Hausch, F. & Jäschke, A. (1997). Libraries of multifunctional RNA conjugates for the selection of new RNA catalysts. Bioconjugate Chem. 8, 885-890.
25. Frauendorf, C. & Jäschke, A. (1998). Catalysis of organic reactions by RNA. Angew. Chem. Int. Ed. 37, 1378-1381.
26. Wu, D.Y. & Herbst, R.M. (1952). Substituted phenyltetrazoles, alkoxynitrophenyle tetrazoles and alkoxyaminophenyl tetrazoles. J. Org. Chem. 17, 216-227.