Control of the chirality and helicity of oligomers of serinol nucleic acid (SNA) by sequence design

Angewandte Chemie - International Edition

Volumn 50, Issue 6, 2011, Pages 1285-1288

  Kashida, Hiromu ^a   Murayama, Keiji ^a   Toda, Takasuke ^a   Asanuma, Hiroyuki ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

antisense agents; artificial oligonucleotides; chirality; helical structures; nucleic acids

Indexed keywords

ANTISENSE AGENT; ARTIFICIAL OLIGONUCLEOTIDES; HELICAL STRUCTURES; HELICITIES; NUCLEOBASES; PROPANEDIOLS; SEQUENCE DESIGNS; THERMAL STABILITY;

BIOMOLECULES; CHIRALITY; ENANTIOMERS; OLIGOMERS; OLIGONUCLEOTIDES; RNA; STEREOCHEMISTRY;

NUCLEIC ACIDS;

OLIGONUCLEOTIDE; PROPANEDIOL DERIVATIVE; SERINE; SERINOL;

ARTICLE; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATION; DNA DENATURATION; NUCLEOTIDE SEQUENCE; STEREOISOMERISM; TRANSITION TEMPERATURE;

BASE SEQUENCE; CIRCULAR DICHROISM; NUCLEIC ACID CONFORMATION; NUCLEIC ACID DENATURATION; OLIGONUCLEOTIDES; PROPYLENE GLYCOLS; SERINE; STEREOISOMERISM; TRANSITION TEMPERATURE;

EID: 79551667548     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201006498     Document Type: Article

References (29)

1. D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893.
2. M. Albrecht, Chem. Rev. 2001, 101, 3457.
3. E. Yashima, K. Maeda, H. Iida, Y. Furusho, K. Nagai, Chem. Rev. 2009, 109, 6102.
4. K. C. Schneider, S. A. Benner, J. Am. Chem. Soc. 1990, 112, 453.
5. S. A. Benner, Acc. Chem. Res. 2004, 37, 784.
6. H. Kaur, B. R. Babu, S. Maiti, Chem. Rev. 2007, 107, 4672.
7. D. H. Appella, Curr. Opin. Chem. Biol. 2009, 13, 687.
8. H. Kashida, X. G. Liang, H. Asanuma, Curr. Org. Chem. 2009, 13, 1065.
9. S. Zhang, C. Switzer, J. C. Chaput, Chem. Biodiversity 2010, 7, 245.
10. L. Zhang, A. Peritz, E. Meggers, J. Am. Chem. Soc. 2005, 127, 4174.
11. M. K. Schlegel, A. E. Peritz, K. Kittigowittana, L. Zhang, E. Meggers, ChemBioChem 2007, 8, 927.
12. M. K. Schlegel, X. Xie, L. Zhang, E. Meggers, Angew. Chem. 2009, 121, 978
13. Angew. Chem. Int. Ed. 2009, 48, 960.
14. M. K. Schlegel, L.-O. Essen, E. Meggers, Chem. Commun. 2010, 46, 1094.
15. H. Asanuma, T. Toda, K. Murayama, X. Liang, H. Kashida, J. Am. Chem. Soc. 2010, 132, 14702.
16. P. Wittung, P. E. Nielsen, O. Buchardt, M. Egholm, B. Norden, Nature 1994, 368, 561.
17. P. E. Nielsen, Acc. Chem. Res. 1999, 32, 624.
18. [18-20].
19. K. S. Ramasamy, W. Seifert, Bioorg. Med. Chem. Lett. 1996, 6, 1799.
20. R. Benhida, M. Devys, J.-L. Fourrey, F. Lecubin, J.-S. Sun, Tetrahedron Lett. 1998, 39, 6167.
21. A. K. Sharma, P. Kumar, K. C. Gupta, Helv. Chim. Acta 2001, 84, 3643.
22. L. Christensen, H. F. Hansen, T. Koch, P. E. Nielsen, Nucleic Acids Res. 1998, 26, 2735.
23. Z. Timár, L. Kovács, G. Kovács, Z. Schmél, J. Chem. Soc. Perkin Trans. 1 2000, 19.
24. T. Kofoed, H. F. Hansen, H. Ãrum, T. Koch, J. Pept. Sci. 2001, 7, 402.
25. Chirality control by sequence design is not possible with natural oligonucleotides or linear peptides:, M. Goodman, M. Chorev, Acc. Chem. Res. 1979, 12, 1.
26. S1 and S2 showed small induced CD signals, which indicated that these strands had slight right-handed helicity even in the single-stranded state.
27. m value of the S1 / S2 duplex was about 10 °C lower than that of the corresponding aTNA duplex, which indicates that the methyl group of threoninol contributed to the high stability of the aTNA duplex (see Table S1 in the Supporting Information).
28. M. T. Record, C. F. Anderson, T. M. Lohman, Q. Rev. Biophys. 1978, 11, 103.
29. S. Nakano, M. Fujimoto, H. Hara, N. Sugimoto, Nucleic Acids Res. 1999, 27, 2957.