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Synlett 1997; 1997(11): 1287-1290
DOI: 10.1055/s-1997-1003
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Amide-Modified Oligonucleotides with Preorganized Backbone and Furanose Rings: Highly Increased Thermodynamic Stability of the Duplexes Formed with their RNA and DNA Complements

Alain De Mesmaeker1 , Jacques Lebreton, Chantal Jouanno, Valérie Fritsch, Romain M. Wolf, Sebastian Wendeborn2
  • 1Novartis AG, Basel, Switzerland, Email: alain.de_mesmaeker@cp.novartis.com; Fax: +41-61-697-8529
  • 2Novartis AG, Basel, Switzerland, Email: sebastian.wendeborn@cp.novartis.com; Fax: +41-61-697-8529
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Publication History

Publication Date:
31 December 2000 (online)

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The amide backbone modification C3'-CH2-CONH-C5' has been further modified by introducing a methyl at C5', either in R or in S configuration. Only the S stereoisomer can adopt the required geometry to fit into a duplex with complementary RNA. Additional O-methyl groups at C2' of the furanose generate antisense oligonucleotides with considerably improved binding affinity to complementary RNA (ΔT m up to 4.4 °C per modification).

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