title: Dinucleotides containing 3'-S-phosphorothiolate linkages.
abstract: The 3'-S-phosphorothiolate (3'-SP) linkage has proven to be a very useful analogue of the phosphodiester 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 corresponding 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 phosphites and also simplifies the deprotection strategy. Full experimental details and spectroscopic data for the synthetic intermediates and the target dinucleotide are provided.
authors: Department of Chemistry, University of Liverpool, Liverpool, L69 7ZD, UK. jwgaynor@liv.ac.uk
authors: James W
authors: JW
authors: Gaynor
authors: Richard
authors: R
authors: Cosstick
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D015226:Dinucleoside Phosphates / Q000138:chemical synthesis* / Q000494:pharmacology; D004720:Endonucleases / Q000037:antagonists & inhibitors / Q000378:metabolism; D006678:HIV / Q000187:drug effects / Q000254:growth & development; D015658:HIV Infections / Q000188:drug therapy / Q000821:virology; D006509:Hepatitis B / Q000188:drug therapy / Q000821:virology; D006515:Hepatitis B virus / Q000187:drug effects / Q000254:growth & development; D006801:Humans; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000494:pharmacology; D009943:Organophosphorus Compounds / Q000737:chemistry; D010710:Phosphates / Q000737:chemistry*; D017905:Phosphites / Q000737:chemistry; D013057:Spectrum Analysis; D013936:Thymidine / Q000737:chemistry
chemical_list: C465503:3'-S-phosphorothiolate; D000998:Antiviral Agents; D015226:Dinucleoside Phosphates; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; D010710:Phosphates; D017905:Phosphites; C434331:phosphoramidite; D004720:Endonucleases; D013936:Thymidine