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Synlett 1999; 1999(S1): 913-916
DOI: 10.1055/s-1999-3113
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Bicyclo[3.2.1]amide-DNA: Synthesis and Base-Pairing Properties

Anita Egger* , Christian J. Leumann
  • *Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern; Fax +41(31)6 31 34 22; E-mail: leumann@ioc.unibe.ch
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Publication Date:
31 December 1999 (online)

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A new oligonucleotide analog, bicyclo[3.2.1]-amide-DNA was synthesized. A homo-adenylate sequence of this analog, efficiently forms hetero-duplexes with complementary natural DNA and RNA. The corresponding homo-thymidylate sequence, however, does not base-pair to complementary DNA and RNA, but forms a stable duplex with the homo-adenylate oligomer of the same backbone type. The structure of this duplex is virtually enantiomeric to that of a natural B-DNA, as inferred from CD-spectroscopy.

oligonucleotides - DNA recognition - RNA - antisense agents