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| - A New Method for the Synthesis of OligodeoxyribonucleotidesContaining 4-N-Alkoxycarbonyldeoxycytidine Derivatives andTheir Hybridization Properties
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| - Oligodeoxyribonucleotides incorporating 4-N-alkoxycarbonyldeoxycytidine derivatives were synthesized on polystyrene-type ArgoPore resins having a new benzyloxy(diisopropyl)silyl linker, byuse of ZnBr2 as the detritylating agent. The first 3‘-terminal thymidine could be attached to theresin by successive in situ reactions of 5‘-O-DMTr-thymidine with diisopropylsilanediyl ditriflateand an ArgoPore resin containing hydroxyl groups. The use of this new silanediyl-type linker allowedrelease of the DNA chain from the resin by treatment with TBAF under neutral conditions. TheTm experiments apparently showed that incorporation of 4-N-alkoxycarbonyldeoxycytidines intoDNA strands resulted in higher hybridization affinity with the complementary DNA strands thanthat of 4-N-acyldeoxycytidines. In addition, comparable Tm studies using oligodeoxyribonucleotidesincorporating acyl (RC(O)−) groups and alkoxyacyl (RO(CH2)nC(O)−) groups having the same chainlength show that the latter tend to exhibit higher Tm values than the former. It turned out that4-N-alkoxycarbonyldeoxycytidines can form base pairs not only with deoxyguanosine but also withdeoxyadenosine. Based on the ab initio calculations of the hydrogen bond energies of the possiblebase pairs formed between 4-N-methoxycarbonyl-1-methylcytosine and 9-methyladenine and theNMR analysis of the base-pairs of 15N-labeled 4-N-alkoxycarbonyldeoxycytidines with deoxyadenosine derivatives, we conclude that the base pair involves two unique hydrogen bonds betweenthe cytosyl 4-NH group and the adenyl N1 atom and between the O atom of the ester group andthe adenyl 6-NH group.
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