Design and synthesis of boronic-acid-labeled thymidine triphosphate for incorporation into DNA

作者：Lin Na; Yan Jun; Huang Zhen; Altier Craig; Li Minyong; Carrasco Nicolas; Suyemoto Mitsu; Johnston Lynette; Wang Siming; Wang Qian; Fang Hao; Caton Williams Julianne; Wang Binghe^*

来源：Nucleic Acids Research, 2007, 35(4): 1222-1229.

DOI：10.1093/nar/gkl1091

The boronic acid moiety is a versatile functional group useful in carbohydrate recognition, glycoprotein pull-down, inhibition of hydrolytic enzymes and boron neutron capture therapy. The incorporation of the boronic-acid group into DNA could lead to molecules of various biological functions. We have successfully synthesized a boronic acid-labeled thymidine triphosphate (B-TTP) linked through a 14-atom tether and effectively incorporated it into DNA by enzymatic polymerization. The synthesis was achieved using the Huisgen cycloaddition as the key reaction. We have demonstrated that DNA polymerase can effectively recognize the boronic acid-labeled DNA as the template for DNA polymerization, that allows PCR amplification of boronic acid-labeled DNA. DNA polymerase recognitions of the B-TTP as a substrate and the boronic acid-labeled DNA as a template are critical issues for the development of DNA-based lectin mimics via in vitro selection.

• 出版日期2007-2