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Communication | Special issue | Vol 5, No. 1, 1976, pp.245-253
Published online, 1st January, 1970
DOI: 10.3987/S-1976-01-0245
Nucleosides and Nucleotides. Part 9. Syntehsis of Dinucleoside Monophosphates Containing 2’-Deoxycytidine and 1-(2’-Deoxy-β-D-ribofuranosyl)-2(1H)-pyridone

Nico Cerletti and Christoph Tamm*

*Institut für Organische Chemie, Universitat Basel, St. Johanns-Ring 19 CH-4056 Basel, Switzerland

Abstract

Condensation of 1-(5’-O-monomethoxytrityl-2’-deoxy-β-D-ribofuranosyl)-2(1H)-pyridone ((MeOTr)Πd, 4) and N4-anisoyl-3’-O-acetyl-2’-deoxycytidine-5’-phosphate (pCdan (Ac), 5) using an excess of dicyclohexylcarbodiimide (DCC) in absolute pyridine yielded the dinucleoside monophosphate (MeOTr)ΠdpCdan (6). Successive removal of the protecting groups of compound 6 led to the partially protected dinucleoside phosphates (MeOTr)ΠdpCd (7) and ΠdpCdan (8), and to the free dinucleoside monophosphate ΠdpCd (9). The enzymatic degradation of 9 by the phosphodiesterases I and II was complete and gave Πd and pCd, and Πdp and Cd respectively with the expected ratio of 1 : l.