Synthesis of fluorescent derivatives of 3′-O-(6-aminohexanoyl)pyrimidine nucleosides 5′-triphosphates that act as DNA polymerase substrates reversibly tagged at C-3′

Abstract

Treatment, of 5′-O-dimethoxytritylthymidine 1 and of 4-N-benzyloxycarbonyl-2′-deoxy-5′-O-dimethoxy-trityl-cytidine 12 with a mixture of 6-(benzyloxycarbonylamino)hexanoic acid, dicyclohexylcarbodiimide and 4-(dimethylamino)pyridine yielded 3′-O-acylated derivatives 2 and 13. These were further converted into 3′-O-(6-aminohexanoyl)thymidine 7 and 3′-O-(6-aminohexanoyl)-2′-deoxycytidine 16 monophosphates. The latter compounds were labelled at the aliphatic amino group with fluorescent probes and transformed into their triphosphates 9 and 18.