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

ABSTRACT: 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.

SUBMITTER: Matyasovsky J

PROVIDER: S-EPMC6680173 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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

Matyašovský Ján J Perlíková Pavla P Malnuit Vincent V Pohl Radek R Hocek Michal M

Angewandte Chemie (International ed. in English) 20161123 51

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-modi ...[more]

PMID: 27879047

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