Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nam. 2, 16610 Prague 6, Czech Republic.
Chemistry. 2012 Mar 26;18(13):4080-7. doi: 10.1002/chem.201103270. Epub 2012 Feb 15.
5-(5-Formylthienyl)-, 5-(4-formylphenyl)- and 5-(2-fluoro-5-formylphenyl)cytosine 2'-deoxyribonucleoside mono- (dC(R)MP) and triphosphates (dC(R)TP) were prepared by aqueous Suzuki-Miyaura cross-coupling of 5-iodocytosine nucleotides with the corresponding formylarylboronic acids. The dC(R)TPs were excellent substrates for DNA polymerases and were incorporated into DNA by primer extension or PCR. Reductive aminations of the model dC(R)MPs with lysine or lysine-containing tripeptide were studied and optimized. In aqueous phosphate buffer (pH 6.7) the yields of the reductive aminations with tripeptide III were up to 25 %. Bioconjugation of an aldehyde-containing DNA with a lysine-containing tripeptide was achieved through reductive amination in yields of up to 90 % in aqueous phosphate buffer.
5-(5-甲酰基噻吩基)-、5-(4-甲酰基苯基)-和 5-(2-氟-5-甲酰基苯基)胞嘧啶 2'-脱氧核苷单-（dC(R)MP）和三磷酸酯（dC(R)TP）通过 5-碘胞嘧啶核苷酸与相应的甲酰芳基硼酸在水溶液中的铃木-宫浦交叉偶联制备。dC(R)TP 是 DNA 聚合酶的优良底物，并通过引物延伸或 PCR 掺入 DNA。对模型 dC(R)MP 与赖氨酸或含赖氨酸的三肽的还原胺化进行了研究和优化。在磷酸缓冲盐水（pH 6.7）中，用三肽 III 进行还原胺化的产率高达 25%。通过在磷酸缓冲盐水介质中进行还原胺化，醛基 DNA 与含赖氨酸的三肽的生物偶联收率高达 90%。
