2-Substituted dATP Derivatives as Building Blocks for Polymerase-Catalyzed Synthesis of DNA Modified in the Minor Groove

被引:49
作者
Matyasovsky, Jan [1 ]
Perlikova, Pavla [1 ]
Malnuit, Vincent [1 ]
Pohl, Radek [1 ]
Hocek, Michal [1 ,2 ]
机构
[1] Czech Acad Sci, Inst Organ Chem & Biochem, Flemingovo Nam 2, Prague 16610 6, Czech Republic
[2] Charles Univ Prague, Dept Organ Chem, Fac Sci, Hlavova 8, Prague 12843 2, Czech Republic
基金
欧盟地平线“2020”;
关键词
bioconjugation; DNA modification; DNA polymerase; nucleotides; fluorescent labelling; NUCLEOSIDE TRIPHOSPHATES; ENZYMATIC-SYNTHESIS; 2'-DEOXYRIBONUCLEOSIDE TRIPHOSPHATES; MODIFIED NUCLEOTIDES; LINKED NUCLEOTIDES; CLICK MODIFICATION; NUCLEIC-ACIDS; CROSS-LINKING; PROBES; INHIBITION;
D O I
10.1002/anie.201609007
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
2-Deoxyadenosine triphosphate (dATP) derivatives bearing diverse substituents (Cl, NH2, CH3, vinyl, ethynyl, and phenyl) at position 2 were prepared and tested as substrates for DNA polymerases. The 2-phenyl-dATP was not a substrate for DNA polymerases, but the dATPs bearing smaller substituents were good substrates in primer-extension experiments, producing DNA substituted in the minor groove. The vinyl-modified DNA was applied in thiol-ene addition and the ethynyl-modified DNA was applied in a CuAAC click reaction to form DNA labelled with fluorescent dyes in the minor groove
引用
收藏
页码:15856 / 15859
页数:4
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