title: Azidopropylvinylsulfonamide as a New Bifunctional Click Reagent for Bioorthogonal Conjugations: Application for DNA-Protein Cross-Linking.
abstract: 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.
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nám. 2, 16610 Prague 6 (Czech Republic).
authors.forename: Jitka
authors.initials: J
authors.lastname: Dadová
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nám. 2, 16610 Prague 6 (Czech Republic).
authors.forename: Milan
authors.initials: M
authors.lastname: Vrábel
authors.affiliation: Institute of Biophysics, Academy of Sciences of the Czech Republic, Kralovopolska 135, 61265 Brno (Czech Republic).
authors.forename: Matej
authors.initials: M
authors.lastname: Adámik
authors.affiliation: Institute of Biophysics, Academy of Sciences of the Czech Republic, Kralovopolska 135, 61265 Brno (Czech Republic).
authors.forename: Marie
authors.initials: M
authors.lastname: Brázdová
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nám. 2, 16610 Prague 6 (Czech Republic).
authors.forename: Radek
authors.initials: R
authors.lastname: Pohl
authors.affiliation: Institute of Biophysics, Academy of Sciences of the Czech Republic, Kralovopolska 135, 61265 Brno (Czech Republic).|Central European Institute of Technology, Masaryk University, Kamenice 753/5, 625 00 Brno (Czech Republic).
authors.forename: Miroslav
authors.initials: M
authors.lastname: Fojta
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nám. 2, 16610 Prague 6 (Czech Republic). hocek@uochb.cas.cz.|Department of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 12843 Prague 2 (Czech Republic). hocek@uochb.cas.cz.
authors.forename: Michal
authors.initials: M
authors.lastname: Hocek
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D001686:Biological Phenomena; D002256:Carbonic Anhydrases / Q000737:chemistry* / Q000378:metabolism; D002384:Catalysis; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry; D061565:Cycloaddition Reaction; D004247:DNA / Q000737:chemistry* / Q000378:metabolism; D006801:Humans; D007202:Indicators and Reagents / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry* / Q000378:metabolism; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000480:Alkynes; D001386:Azides; D007202:Indicators and Reagents; C000608092:N-(3-azidopropyl)vinylsulfonamide; D010455:Peptides; D013438:Sulfhydryl Compounds; D013449:Sulfonamides; D014753:Vinyl Compounds; D003300:Copper; D004247:DNA; D002256:Carbonic Anhydrases
keywords: biotransformations; click chemistry; conjugation; nucleic acids; proteins