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

共 159 条

[1] Rapid HATU-Mediated Solution Phase siRNA Conjugation
Aaronson, Jeffrey G.
Klein, Lee J.
Momose, Aaron A.
O'Brien, Ann M.
Shaw, Anthony W.
Tucker, Thomas J.
Yuan, Yu
Tellers, David M.
[J]. BIOCONJUGATE CHEMISTRY, 2011, 22 (08) : 1723 - 1728
[2] [Anonymous], 2013, ANGEW CHEM, V125, P10747
[3] [Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1038/NMETH.4403
[4] [Anonymous], 2010, ANGEW CHEM
[5] Arndt S., 2014, ANGEW CHEM, V126, P14808
[6] "Photoclick" Postsynthetic Modification of DNA
Arndt, Stefanie
Wagenknecht, Hans-Achim
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (52) : 14580 - 14582
[7] DNA conjugation by the Staudinger ligation: New thymidine analogues
Baccaro, Anna
Weisbrod, Samuel H.
Marx, Andreas
[J]. SYNTHESIS-STUTTGART, 2007, 13 (13): : 1949 - 1954
[8] Enzymatic Synthesis of Organic-Polymer-Grafted DNA
Baccaro, Anna
Marx, Andreas
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (01) : 218 - 226
[9] Azidophenyl as a click-transformable redox label of DNA suitable for electrochemical detection of DNA-protein interactions
Balintova, Jana
Spacek, Jan
Pohl, Radek
Brazdova, Marie
Havran, Ludek
Fojta, Miroslav
Hocek, Michal
[J]. CHEMICAL SCIENCE, 2015, 6 (01) : 575 - 587
[10] Becer C.R., 2009, Angew. Chem, V121, P4998

← 1 2 3 4 5 6 7 8 9 10 →