Assessment of the Full Compatibility of Copper(I)-Catalyzed Alkyne-Azide Cycloaddition and Oxime Click Reactions for bis-Labelling of Oligonucleotides

被引:3
作者
Estalayo-Adrian, Sandra [1 ]
Lartia, Remy [1 ]
Meyer, Albert [2 ]
Vasseur, Jean-Jacques [2 ]
Morvan, Francois [2 ]
Defrancq, Eric [1 ]
机构
[1] Univ Grenoble Alpes, UMR CNRS 5250, Dept Chim Mol, F-38041 Grenoble 9, France
[2] Univ Montpellier, CNRS, UMR 5247, Inst Biomol Max Mousseron, F-34095 Montpellier 5, France
关键词
click chemistry; conjugates; CuAAC reactions; oligonucleotides; oxime ligation; CHEMISTRY; STRATEGIES;
D O I
10.1002/open.201402099
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The conjugation of oligonucleotides with reporters is of great interest for improving their intrinsic properties or endowing new ones. In this context, we report herein a new procedure for the bis-labelling of oligonucleotides through oxime ligation (Click-O) and copper(I)-catalyzed alkyne-azide cycloaddition (Click-H). 5-Azido and 3-aldehyde' precursors were incorporated into oligonucleotides, and subsequent coupling reactions through Click-O and Click-H (or vice versa) were successfully achieved. In particular, we exhaustively investigated the full compatibility of each required step for both tethering strategies. The results demonstrate that click Huisgen and click oxime reactions are fully compatible. However, whilst both approaches can deliver the targeted doubly conjugated oligonucleotide, the route involving click oxime ligation prior to click Huisgen is significantly more successful. Thus the reactions investigated here can be considered to be key elements of the chemical toolbox for the synthesis of highly sophisticated bioconjugates.
引用
收藏
页码:169 / 173
页数:5
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