Azidopropylvinylsulfonamide as a New Bifunctional Click Reagent for Bioorthogonal Conjugations: Application for DNA-Protein Cross-Linking

0453444 - ÚOCHB 2016 RIV DE eng J - Journal Article
Daďová, Jitka - Vrábel, Milan - Adámik, Matěj - Brázdová, Marie - Pohl, Radek - Fojta, Miroslav - Hocek, Michal
Azidopropylvinylsulfonamide as a New Bifunctional Click Reagent for Bioorthogonal Conjugations: Application for DNA-Protein Cross-Linking.
Chemistry - A European Journal. Roč. 21, č. 45 (2015), s. 16091-16102. ISSN 0947-6539. E-ISSN 1521-3765
R&D Projects: GA ČR GBP206/12/G151
Institutional support: RVO:61388963 ; RVO:68081707
Keywords : biotransformations * click chemistry * conjugation * nucleic acids * proteins
Subject RIV: CC - Organic Chemistry
Impact factor: 5.771, year: 2015

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.
Permanent Link: http://hdl.handle.net/11104/0254254