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Squaramate‐Modified Nucleotides and DNA for Specific Cross‐Linking with Lysine‐Containing Peptides and Proteins
Author(s) -
Ivancová Ivana,
Pohl Radek,
Hubálek Martin,
Hocek Michal
Publication year - 2019
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.201906737
Subject(s) - dna , chemistry , nucleotide , nucleic acid , biochemistry , primer (cosmetics) , dna polymerase , polymerase , lysine , microbiology and biotechnology , biology , amino acid , gene , organic chemistry
Squaramate‐linked 2′‐deoxycytidine 5′‐ O ‐triphosphate was synthesized and found to be good substrate for KOD XL DNA polymerase in primer extension or PCR synthesis of modified DNA. The resulting squaramate‐linked DNA reacts with primary amines to form a stable diamide linkage. This reaction was used for bioconjugations of DNA with Cy5 and Lys‐containing peptides. Squaramate‐linked DNA formed covalent cross‐links with histone proteins. This reactive nucleotide has potential for other bioconjugations of nucleic acids with amines, peptides or proteins without need of any external reagent.