Abstract
The synthesis of a novel ribonucleotide analog 2'-thio-2' deoxycytidine 2':3'-O,S-phosphorothioate is described. In the first step, 2,2'-anhydro 1-beta-D-arabinosylcytosine was thiophosphorylated by the action of dithiophosphate, a process which gave predominantly the 3'-O-phosphorothioate isomer. An intramolecular displacement reaction led to the formation of the title compound. Structure and reactivity of this thioanalog differ substantially from 2':3'-CMP.
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- Brennan T., Sundaralingam M. Molecular structure of 2,2'-anhydro-1- -D-arabinofuranosyl cytosine hydrochloride (cyclo ara-C): a highly rigid nucleoside. Biochem Biophys Res Commun. 1973 Jun 19;52(4):1348–1353. doi: 10.1016/0006-291x(73)90649-9. [DOI] [PubMed] [Google Scholar]
- Doerr I. L., Fox J. J. Nucleosides. XXXIX. 2'-deoxy-2'-fluorocytidine, 1-beta-D-arabinofuranosyl-2-amino-1,4(2H)-4-iminopyrimidine, and related derivatives. J Org Chem. 1967 May;32(5):1462–1471. doi: 10.1021/jo01280a035. [DOI] [PubMed] [Google Scholar]
- Eckstein F. Nucleoside phosphorothioates. J Am Chem Soc. 1970 Jul 29;92(15):4718–4723. doi: 10.1021/ja00718a039. [DOI] [PubMed] [Google Scholar]
- Lavallee D. K., Coulter C. L. Structural chemistry of cyclic nucleotides. 3. Proton magnetic resonance studies of -pyrimidine nucleotides. J Am Chem Soc. 1973 Jan 24;95(2):576–581. doi: 10.1021/ja00783a043. [DOI] [PubMed] [Google Scholar]