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Therapeutic Oligonucleotides, ch 2: Diverse Dinucleotides Containing 3′-S-Phosphorothiolate Linkages

  • Gaynor J
  • Cosstick R
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Abstract

Abstract The 3′-S-phosphorothiolate (3′-SP) linkage has proven to be a very useful analogue of the phosphodi- ester group in nucleic acid derivatives; it is achiral and also shows good resistance to nucleases. Whilst oligonucleotides containing a 3′-SP linkage are best prepared using phosphoramidite chemistry, the cor- responding dinucleotides are most efficiently synthesised using a Michaelis–Arbuzov reaction between a nucleoside 5′-phosphite and a nucleoside 3′-S-disulphide. The method described here is for a thymidine dinucleotide and is based on the use of a silyl phosphite, which is more reactive than simple alkyl phos- phites and also simplifies the deprotection strategy. Full experimental details and spectroscopic data for the synthetic intermediates and the target dinucleotide are provided. Key

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Gaynor, J. W., & Cosstick, R. (2011). Therapeutic Oligonucleotides, ch 2: Diverse Dinucleotides Containing 3′-S-Phosphorothiolate Linkages. Methods in Molecular Biology, 764, 17–30. Retrieved from http://www.springerlink.com/index/10.1007/978-1-61779-188-8

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