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Synlett 1993; 1993(10): 733-736
DOI: 10.1055/s-1993-22588
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Amides as Substitute for the Phosphodiester Linkage in Antisense Oligonucleotides

Alain De Mesmaeker* , Jacques Lebreton, Adrian Waldner, Valérie Fritsch, Romain M. Wolf, Susan M. Freier
  • *Central Research Laboratories, CIBA-GEIGY Ltd., CH-4002 Basel, Switzerland
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Publication Date:
19 March 2002 (online)

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The synthesis of a thymidine dimer in which the natural phosphodiester linkage has been replaced by an amide (3′-CH2-CH2-NH-CO-4′) is described. This new dimer was incorporated into oligonucleotides. Measurement of melting temperatures (Tm) of DNA/RNA duplexes and the nuclease resistance are presented. Preliminary results of molecular mechanics are included.