Z-DNA formation by 2'-C-ethynyl-modified oligonucleotides

Synlett

Volumn , Issue SPEC. ISS., 1999, Pages 905-908

  Buff, Rolf ^a   Hunziker, Jürg ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

DNA; Oligonucleotide; Z DNA

Indexed keywords

GUANINE DERIVATIVE; OLIGONUCLEOTIDE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; HYDRATION; REACTION ANALYSIS; REDUCTION; SALINITY; STEREOCHEMISTRY; SYNTHESIS; THERMOSTABILITY;

EID: 0033020054     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3180     Document Type: Article

References (18)

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8. Sproat, B. S.; Beijer, B.; Grøtli, M.; Ryder, U.; Morand, K. L.; Lamond, A. I. J. Chem. Soc, Perkins Trans. 1 1994, 419.
9. Attempts to isolate the pure ketone by chromatography or the addition of drying agents failed. Therefore, the 1:1 mixture was directly used in the next step without further purification.
10. Buff, R.; Stöckli-Evans, H.; Hunziker, J. Acta Cryst. C 1998, 54, 1860.
11. 2′,3′ = 9.8 Hz.
12. 4: C 52.02, H 5.24, N 24.26, found: C 52.09, H 5.51, N 24.01.
13. Conolly, B. A, In Oligonucteotides and Analogues; Eckstein, F. Ed.; Oxford University Press: Oxford, 1991, pp 155-183.
14. Oligonucleotides 9 -16 were synthesized on a Pharmacia Gene Assembler Plus using the standard protocol, changing the length of the coupling step to 15min. Deprotection was carried out in conc. ammonia at 55°C for 30min.
15. Wu, X.; Pitsch, S. Nucleic Acids Res. 1998, 26, 4315.
16. +-form): 9: calc. 2034.4, found 2032.4; 10: calc. 1793.2, found 1791.8; 11: calc. 1842.3, found 1840.5; 12: calc. 1818.3, found 1822.7; 13; calc. 1818.3, found 1818.7; 14: calc. 1793.2, found 1791.8; 15: calc. 1866.3, found 1864.1; 16: calc. 1866.3, found 1866.6. Matrix conditions as described in: Pieles, U.; Zürcher, W.; Schär, M.; Moser, H. E. Nucleic Acids Res. 1993, 21, 3191.
17. EtG) exclusively adopts a B-form conformation irrespective of salt concentration.
18. Saenger, W. in Principles of Nucleic Acid Structure; Springer: New York, 1984, pp 283-297.