Bicyclo[3.2.1]-DNA, a new DNA analog with a rigid backbone and flexibly linked bases: Pairing properties with complementary DNA

Chemistry and Biology

Volumn 5, Issue 4, 1998, Pages 209-216

  Epple, Carl ^a   Leumann, Christian ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

Backbone modification; Bicyclo 3.2.1 DNA; Conformational restriction; DNA analog; Oligonucleotides

Indexed keywords

EID: 0032054719     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(98)90634-2     Document Type: Article

References (24)

1. Hunziker, J. & Leumann, C. (1995). Nucleic acid analogues: synthesis and properties. In Modern Synthetic Methods. (Ernst, B., Leumann, C. eds.), pp. 331-417, Verlag Helvetica Chimica Acta, Basel.
2. Herdewijn, P. (1996). Targeting RNA with conformationally restricted oligonucleotides. Liebigs Ann. 1337-1348.
3. Kool, E.T. (1997). Preorganization of DNA: design principles for improving nucleic acid recognition by synthetic oligonucleotides. Chem. Rev. 97, 1473-1487.
4. Niemeyer, CM (1997). DNA as a material for nanotechnology. Angew. Chem. Int. Ed. Engl. 36, 585-587.
5. Bolli, M., Litten, C., Schütz, R. & Leumann, C. (1996). Bicyclo-DNA: a Hoogsteen-selective pairing system. Chem. Biol. 3, 197-206.
6. Bolli, M., Trafelet, H.U. & Leumann, C. (1996). Watson-Crick base-pairing properties of bicyclo-DNA. Nucleic Acids Res. 24, 4660-4667.
7. Van Aerschot, A., Verheggen, I., Hendrix, C. & Herdewijn, P. (1995). 1,5-Anhydrohexitol nucleic acids, a new promising antisense construct. Angew. Chem. Int. Ed. Engl. 34, 1338-1339.
8. Hendrix, C., Rosemeyer, H., Verheggen, I., Seela, F., Van Aerschot, A. & Herdewijn, P. (1997). 1,5,-Anhydrohexitol oligonucleotides: synthesis, base-pairing and recognition by regular oligodeoxyribonucleotides and oligoribonucleotides. Chem. Eur. J. 3, 110-120.
9. Schneider, K.C. & Benner, S.A. (1990). Oligonucleotides containing flexible nucleoside analogues. J. Am. Chem. Soc. 112, 453-455.
10. Hunziker, J., et al., & Eschenmoser, A. (1993). Why pentose and not hexose nucleic acids?, part III, oligo(2′,3′-dideoxy-β D-glucopyranosyl) nucleotides (homo-DNA): base-pairing properties. Helv. Chim. Acta 76, 259-352.
11. 15N NMR spectroscopic investigation of ddGlc (A-A-A-A-A-T-T-T-T-T) in aqueous solution. Helv. Chim. Acta 76, 2701-2756.
12. Nielsen, P., Kirpekar, F. & Wengel, J. (1994). Incorporation of (R)- and (S)-3′,4′-seco-thymidine into oligodeoxynucleotides: hybridization properties and enzymatic stability. Nucleic Acids Res. 22, 703-710.
13. Peng, L. & Roth, H.-J. (1997). Synthesis and properties of 2′-deoxy-1′,2′-seco-D-ribosyl(5′→3′) oligonucleotides (=1′,2′-Seco-DNA) containing adenine and thymine. Helv. Chim. Acta 80, 1494-1512.
14. Egger, A., Hunziker, J., Rihs, G. & Leumann, C. (1998). Synthesis of bridgehead-functionalized bicyclo[3.2.1]octanes via titanium and tributyltinhydride induced pinakol coupling, synthesis of conformationally rigid glycerol substitutes. Helv. Chim. Acta 81, in press.
15. Vorbrüggen, H. & Bennua, B. (1981). A new simplified nucleoside synthesis. Chem. Ber. 114, 1279-1286.
16. Petersheim, M. & Turner, D. (1983). Base-stacking and base-pairing contributions to helix stability: thermodynamics of double-helix formation with CCGG, CCGGp, CCGGAp, ACCGGp, CCGGUp and ACCGGUp. Biochemistry 22, 256-263.
17. Breslauer, K.J., Frank, R., Blöcker, H. & Marky, L.A. (1986). Predicting DNA duplex stability from the base sequence. Proc. Natl Acad. Sci. USA 83, 3746-3750.
18. Egholm, M., et al., & Nielsen, P.E. (1993). PNA hybridizes to complementary oligonucleotides obeying the Watson-Crick hydrogen bonding rules. Nature 365, 566-568.
19. 1H-NMR, anti-parallel self recognition and conformation of the unnatural hexadeoxyribonucleotides α-d(CATGCG) and α-d(CGCATG). α-oligodeoxynucleotides as potential cellular probes for gene control. Nucleic Acids Res. 15, 4241-4255.
20. 1H-NMR. Nucleic Acids Res. 15, 7027-7044.
21. Pieles, U., Zürcher, W., Schär, M. & Moser, H.E. (1993). Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: a powerful tool for the mass and sequence analysis of natural and modified oligonucleotides. Nucleic Acids Res. 21, 3191-3196.
22. Marky, L.A. & Breslauer, K.J. (1987). Calculating thermodynamic data for transitions of any molecularity from equilibrium melting curves. Biopolymers 26, 1601-1620.
23. Bolli, M., Lubini, P. & Leumann, C. (1995). Nucleic acid analogs with restricted conformational flexibility in the sugar-phosphate backbone ('Bicyclo-DNA', part 5), synthesis, characterization and pairing properties of oligo-D-(bicyclodeoxynucleotides) of the bases adenine and thymine (α-Bicyclo-DNA). Helv. Chim. Acta 78, 2077-2096.
24. Marky, L.A. & Breslauer, K. J. (1987). Calculating thermodynamic data for transitions of any molecularity from equilibrium melting curves. Biopolymers 26, 1601-1620.