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

• Authors: DADOVÁ Jitka; VRÁBEL Milan; ADÁMIK Matej; BRÁZDOVÁ Marie; POHL Radek; FOJTA Miroslav; HOCEK Michal
• Year of publication: 2015
• Type: Article in Periodical
• Magazine / Source: Chemistry - A European Journal
• MU Faculty or unit: Central European Institute of Technology
• Web: http://onlinelibrary.wiley.com/doi/10.1002/chem.201502209/epdf
• Doi: http://dx.doi.org/10.1002/chem.201502209
• Field: Biochemistry
• Keywords: biotransformations; click chemistry; conjugation; nucleic acids; proteins
• Description: 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.

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