Dai Qing, Deb Shirshendu K, Hougland James L, Piccirilli Joseph A
Howard Hughes Medical Institute, The University of Chicago, MC 1028, Chicago, IL 60637, USA.
Bioorg Med Chem. 2006 Feb 1;14(3):705-13. doi: 10.1016/j.bmc.2005.08.050. Epub 2005 Oct 3.
2'-Amino-2'-deoxynucleosides and oligonucleotides containing them have proven highly effective for an array of biochemical applications. The guanosine analogue and its phosphoramidite derivatives have been accessed previously from 2'-amino-2'-deoxyuridine by transglycosylation, but with limited overall efficiency and convenience. Using simple modifications of known reaction types, we have developed useful protocols to obtain 2'-amino-2'-deoxyguanosine and two of its phosphoramidite derivatives with greater convenience, fewer steps, and higher yields than reported previously. These phosphoramidites provide effective synthons for the incorporation of 2'-amino-2'-deoxyguanosine into oligonucleotides.
2'-氨基-2'-脱氧核苷及含有它们的寡核苷酸已被证明在一系列生化应用中非常有效。鸟苷类似物及其亚磷酰胺衍生物此前已通过转糖基化反应从2'-氨基-2'-脱氧尿苷制得，但总体效率和便利性有限。通过对已知反应类型进行简单修改，我们开发出了实用的方法，能够更方便、步骤更少且产率更高地获得2'-氨基-2'-脱氧鸟苷及其两种亚磷酰胺衍生物，这是此前报道中所没有的。这些亚磷酰胺为将2'-氨基-2'-脱氧鸟苷掺入寡核苷酸提供了有效的合成子。
