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

基金：

欧盟地平线“2020”;

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

页码：16091 / 16102

页数：12

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