Zielinski W S, Orgel L E
Nucleic Acids Res. 1985 Apr 11;13(7):2469-84. doi: 10.1093/nar/13.7.2469.
3'-amino-3'-deoxyuridine reacts with the nucleoside 5'-phosphorimidazolides in aqueous solution to give dinucleoside phosphoramidates. The reactions are one to two orders of magnitude faster than the corresponding reactions of uridine. In the presence of poly(C) or poly(dC) it is known that guanosine-5'-phosphorimidazolide does not condense efficiently or regiospecifically. However, the introduction of a methyl group at the 2-position of the imidazole ring leads to efficient synthesis of long 3'-5'-linked oligomers. The corresponding imidazole derivatives of 3'-amino-3'-deoxyguanosine-5'-phosphate both condense on these templates to give virtually identical families of products. Our results suggest that the intrinsically greater nucleophilicity of the amine groups will permit a much wider range of efficient template-directed syntheses with 3'-amino-3'-deoxynucleoside derivatives than with the corresponding derivatives of the parent nucleosides.
3'-氨基-3'-脱氧尿苷在水溶液中与核苷5'-磷酰咪唑化物反应生成二核苷磷酸酰胺。这些反应比尿苷的相应反应快一到两个数量级。已知在聚（C）或聚（dC）存在下，鸟苷-5'-磷酰咪唑化物不能有效地或区域特异性地缩合。然而，在咪唑环的2-位引入甲基会导致高效合成长的3'-5'-连接的寡聚物。3'-氨基-3'-脱氧鸟苷-5'-磷酸的相应咪唑衍生物都在这些模板上缩合，得到几乎相同的产物家族。我们的结果表明，与母体核苷的相应衍生物相比，胺基固有的更强亲核性将使3'-氨基-3'-脱氧核苷衍生物能够进行更广泛的高效模板导向合成。
