Universal initiator nucleotides for the enzymatic synthesis of 5′-amino- and 5′-thiol-modified RNA

Biochemical and Biophysical Research Communications

Volumn 344, Issue 3, 2006, Pages 887-892

  Schlatterer, Jörg C ^a   Jäschke, Andres ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Conjugation; In vitro selection; Ribozymes; Transcription

Indexed keywords

ETHYLENE GLYCOL; GLYCOL; GUANOSINE; GUANOSINE PHOSPHATE; NUCLEOTIDE; RIBOZYME; RNA POLYMERASE; TRANSFER RNA;

ARTICLE; CHEMICAL MODIFICATION; IN VITRO STUDY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PRIORITY JOURNAL; RNA TRANSCRIPTION; SYNTHESIS;

CODON, INITIATOR; DNA-DIRECTED RNA POLYMERASES; NUCLEOTIDES; RNA; RNA, CATALYTIC; SULFHYDRYL COMPOUNDS; VIRAL PROTEINS;

EID: 33646151631     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2006.03.218     Document Type: Article

References (28)

1. T.R. Cech, D. Herschlag, in: F. Eckstein, D.M.J. Lilley (Eds.), Catalytic RNA, Springer, Heidelberg, 1996, pp. 1-17.
2. Griffin Jr. E.A., Qin Z., Michels Jr. W.J., and Pyle A.M. Group II intron ribozymes that cleave DNA and RNA linkages with similar efficiency, and lack contacts with substrate 2′-hydroxyl groups. Chem. Biol. 2 (1995) 761-770
3. Sontheimer E.J., and Steitz J.A. The U5 and U6 small nuclear RNAs as active site components of the spliceosome. Science 262 (1993) 1989-1996
4. Strobel S.A., and Shetty K. Defining the chemical groups essential for Tetrahymena group I intron function by nucleotide analog interference mapping. Proc. Natl. Acad. Sci. USA 94 (1997) 2903-2908
5. Uhlmann E., and Peyman A. Antisense oligonucleotides: a new therapeutic principle. Chem. Rev. 90 (1990)
6. Pitulle C., Kleineidam R.G., Sproat B., and Krupp G. Initiator oligonucleotides for the combination of chemical and enzymatic RNA synthesis. Gene 112 (1992) 101-105
7. Hausch F., and Jaschke A. Libraries of multifunctional RNA conjugates for the selection of new RNA catalysts. Bioconjug. Chem. 8 (1997) 885-890
8. Moore M.J., and Query C.C. Joining of RNAs by splinted ligation. Methods Enzymol. 317 (2000) 109-123
9. Fiammengo R., and Jäschke A. Nucleic acid enzymes. Curr. Opin. Biotechnol. 16 (2005) 614-621
10. Weigand B.S., Zerressen A., Schlatterer J.C., Helm M., and Jäschke A. Catalytically active RNA molecules: tools in organic chemistry. In: Klussmann S. (Ed). The Aptamer Handbook (2006), Wiley-VCH, Weinheim 211-227
11. Fiammengo R., Musilek K., and Jäschke A. Efficient preparation of organic substrate-RNA conjugates via in vitro transcription. J. Am. Chem. Soc. 127 (2005) 9271-9276
12. Hausch F., and Jäschke A. Multifunctional DNA conjugates for the in vitro selection of new catalysts. Nucleic Acids Res. 28 (2000) E35
13. Seelig B., and Jäschke A. Site-specific modification of enzymically synthesized RNA: transcription initiation and Diels-Alder reaction. Tetrahedron Lett. 38 (1997) 7729-7732
14. Seelig B., and Jäschke A. Ternary conjugates of guanosine monophosphate as initiator nucleotides for the enzymatic synthesis of 5′-modified RNAs. Bioconjug. Chem. 10 (1999) 371-378
15. Keiper S., Bebenroth D., Seelig B., Westhof E., and Jäschke A. Architecture of a Diels-Alderase ribozyme with a preformed catalytic pocket. Chem. Biol. 11 (2004) 1217-1227
16. Seelig B., and Jäschke A. A small catalytic RNA motif with Diels-Alderase activity. Chem. Biol. 6 (1999) 167-176
17. Seelig B., Keiper S., Stuhlmann F., and Jäschke A. Enantioselective ribozyme catalysis of a bimolecular cycloaddition reaction. Angew. Chem. Int. Ed. Engl. 39 (2000) 4576-4579
18. Serganov A., Keiper S., Malinina L., Tereshko V., Skripkin E., Höbartner C., Polonskaia A., Phan A.T., Wombacher R., Micura R., Dauter Z., Jäschke A., and Patel D.J. Structural basis for Diels-Alder ribozyme-catalyzed carbon-carbon bond formation. Nat. Struct. Mol. Biol. 12 (2005) 218-224
19. Stuhlmann F., and Jäschke A. Characterization of an RNA active site: interactions between a Diels-Alderase ribozyme and its substrates and products. J. Am. Chem. Soc. 124 (2002) 3238-3244
20. Wombacher R., Keiper S., Suhm S., Serganov A., Patel D.J., and Jäschke A. Control of stereoselectivity in an enzymatic reaction by backdoor access. Angew. Chem. Int. Ed. Engl. 45 (2006) 2469-2472
21. Huang F., Wang G., Coleman T., and Li N. Synthesis of adenosine derivatives as transcription initiators and preparation of 5′ fluorescein- and biotin-labeled RNA through one-step in vitro transcription. RNA 9 (2003) 1562-1570
22. Milligan M.J., Groebe D.R., Witherell G.W., and Uhlenbeck O.C. Oligoribonucleotide synthesis using T7 RNA polymerase and synthetic DNA templates. Nucleic Acids Res. 15 (1987) 8783-8798
23. F. Eckstein, in: F. Eckstein (Ed.), Oligonucleotides and Analogues. A Practical Approach, Oxford University Press, IRL Press, NY, 1991, p. 190.
24. Tarasow T.M., Tarasow S.L., and Eaton B.E. RNA-catalysed carbon-carbon bond formation. Nature 389 (1997) 54-57
25. Wiegand T.W., Janssen R.C., and Eaton B.E. Selection of RNA amide synthases. Chem. Biol. 4 (1997) 675-683
26. Golas M.M., Sander B., Will C.L., Lührmann R., and Stark H. Major conformational change in the complex SF3b upon integration into the spliceosomal U11/U12 di-snRNP as revealed by electron cryomicroscopy. Mol. Cell 17 (2005) 869-883
27. Schlatterer J.C., Crayton S.H., and Greenbaum N.L. Conformation of the group II intron branch site in solution. J. Am. Chem. Soc. 128 (2006) 3866-3867
28. Zhang L., and Doudna J.A. Structural insights into group II intron catalysis and branch-site selection. Science 295 (2002) 2084-2088