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Azidopropylvinylsulfonamide as a New Bifunctional Click Reagent for Bioorthogonal Conjugations: Application for DNA–Protein Cross‐Linking
Author(s) -
Dadová Jitka,
Vrábel Milan,
Adámik Matej,
Brázdová Marie,
Pohl Radek,
Fojta Miroslav,
Hocek Michal
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502209
Subject(s) - bioconjugation , bioorthogonal chemistry , click chemistry , chemistry , bifunctional , reagent , combinatorial chemistry , biomolecule , covalent bond , azide , cycloaddition , dna , alkyne , cysteine , organic chemistry , biochemistry , enzyme , catalysis
N ‐(3‐Azidopropyl)vinylsulfonamide was developed as a new bifunctional bioconjugation reagent suitable for the cross‐linking of biomolecules through copper(I)‐catalyzed azide–alkyne cycloaddition and thiol Michael addition reactions under biorthogonal conditions. The reagent is easily clicked to an acetylene‐containing DNA or protein and then reacts with cysteine‐containing peptides or proteins to form covalent cross‐links. Several examples of bioconjugations of ethynyl‐ or octadiynyl‐modified DNA with peptides, p53 protein, or alkyne‐modified human carbonic anhydrase with peptides are given.