Anaerobic conditions to reduce oxidation of proteins and to accelerate the copper-catalyzed "Click" reaction with a water-soluble bis(triazole) ligand

被引:35
作者
Kumar, Amit [1 ]
Li, King [2 ]
Cai, Chengzhi [1 ]
机构
[1] Univ Houston, Dept Chem, Houston, TX 77204 USA
[2] Methodist Hosp, Res Inst, Dept Radiol, Houston, TX 77030 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
AZIDE-ALKYNE CYCLOADDITION; TERMINAL ALKYNES; IN-VIVO; AMINOGUANIDINE;
D O I
10.1039/c0cc05376g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Oxidation of protein (bovine albumin serum) by air still occurred under the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction conditions even in the presence of a Cu(I)-stabilizing tris(triazole) ligand. Anaerobic conditions not only avoided the oxidation of the protein, but also greatly accelerated the CuAAC reaction using a water-soluble bis(triazole) Cu(I) ligand.
引用
收藏
页码:3186 / 3188
页数:3
相关论文
共 21 条
[1]   Efficient scavenging of fatty acid oxidation products by aminoguanidine [J].
AlAbed, Y ;
Bucala, R .
CHEMICAL RESEARCH IN TOXICOLOGY, 1997, 10 (08) :875-879
[2]   Site-Specific Incorporation of p-Propargyloxyphenylalanine in a Cell-Free Environment for Direct Protein-Protein Click Conjugation [J].
Bundy, Bradley C. ;
Swartz, James R. .
BIOCONJUGATE CHEMISTRY, 2010, 21 (02) :255-263
[3]   Protein carbonyl measurement by a sensitive ELISA method [J].
Buss, H ;
Chan, TP ;
Sluis, KB ;
Domigan, NM ;
Winterbourn, CC .
FREE RADICAL BIOLOGY AND MEDICINE, 1997, 23 (03) :361-366
[4]   Polytriazoles as copper(I)-stabilizing ligands in catalysis [J].
Chan, TR ;
Hilgraf, R ;
Sharpless, KB ;
Fokin, VV .
ORGANIC LETTERS, 2004, 6 (17) :2853-2855
[5]   Antioxidant properties of aminoguanidine [J].
Courderot-Masuyer, C ;
Dalloz, F ;
Maupoil, V ;
Rochette, L .
FUNDAMENTAL & CLINICAL PHARMACOLOGY, 1999, 13 (05) :535-540
[6]   Peptide/protein-polymer conjugates: synthetic strategies and design concepts [J].
Gauthier, Marc A. ;
Klok, Harm-Anton .
CHEMICAL COMMUNICATIONS, 2008, (23) :2591-2611
[7]   Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides [J].
Hein, Jason E. ;
Fokin, Valery V. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (04) :1302-1315
[8]   Electrochemically protected copper(I)-catalyzed azide-alkyne cycloaddition [J].
Hong, Vu ;
Udit, Andrew K. ;
Evans, Richard A. ;
Finn, M. G. .
CHEMBIOCHEM, 2008, 9 (09) :1481-1486
[9]   Analysis and Optimization of Copper-Catalyzed Azide-Alkyne Cycloaddition for Bioconjugation [J].
Hong, Vu ;
Presolski, Stanislav I. ;
Ma, Celia ;
Finn, M. G. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9879-9883
[10]   Cu-free click cycloaddition reactions in chemical biology [J].
Jewett, John C. ;
Bertozzi, Carolyn R. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (04) :1272-1279