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

被引：22
|
作者：
Dadova, Jitka [1 ]
Vrabel, Milan [1 ]
Adamik, Matej [2 ]
Brazdova, Marie [2 ]
Pohl, Radek [1 ]
Fojta, Miroslav [2 ,4 ]
Hocek, Michal [1 ,3 ]
机构：
[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, Gilead Sci & IOCB Res Ctr, Prague 16610 6, Czech Republic
[2] Acad Sci Czech Republ, Inst Biophys, CS-61265 Brno, Czech Republic
[3] Charles Univ Prague, Dept Organ Chem, Fac Sci, Prague 12843 2, Czech Republic
[4] Masaryk Univ, Cent European Inst Technol, Brno 62500, Czech Republic
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 45期
关键词：
biotransformations; click chemistry; conjugation; nucleic acids; proteins; GENETIC-CODE EXPANSION; SOLID-PHASE SYNTHESIS; NUCLEOSIDE TRIPHOSPHATES; POLYMERASE SYNTHESIS; ENZYMATIC-SYNTHESIS; AMINO-ACIDS; 2'-DEOXYRIBONUCLEOSIDE TRIPHOSPHATES; POSTSYNTHETIC MODIFICATION; MODIFIED OLIGONUCLEOTIDES; BUILDING-BLOCKS;
D O I：
10.1002/chem.201502209
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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.
引用
收藏
页码：16091 / 16102
页数：12
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