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2‐Substituted dATP Derivatives as Building Blocks for Polymerase‐Catalyzed Synthesis of DNA Modified in the Minor Groove
Author(s) -
Matyašovský Ján,
Perlíková Pavla,
Malnuit Vincent,
Pohl Radek,
Hocek Michal
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201609007
Subject(s) - dna , dna polymerase , minor groove , polymerase , chemistry , primer (cosmetics) , stereochemistry , biochemistry , organic chemistry
2′‐Deoxyadenosine triphosphate (dATP) derivatives bearing diverse substituents (Cl, NH 2 , CH 3 , 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