Extent of the Oxidative Side Reactions to Peptides and Proteins During the CuAAC Reaction

The copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction is a powerful tool for bioconjugation of biomolecules, particularly proteins and peptides. The major drawback limiting the use of the CuAAC reaction in biological systems is the copper-mediated formation of reactive oxygen species (ROS...

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Bibliographic Details
Published in:Bioconjugate chemistry 2016-10, Vol.27 (10), p.2315-2322
Main Authors: Li, Siheng, Cai, Honghao, He, Jilin, Chen, Haoqing, Lam, Srujana, Cai, Tao, Zhu, Zhiling, Bark, Steven J, Cai, Chengzhi
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Azides - chemistry
Chromatography
Copper
Copper - chemistry
Free Radical Scavengers - chemistry
Molecules
Oxidation
Oxidation-Reduction
Peptide Library
Peptides
Peptides - chemistry
Proteins
Proteins - chemistry
Serum Albumin, Bovine - chemistry
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Summary:The copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction is a powerful tool for bioconjugation of biomolecules, particularly proteins and peptides. The major drawback limiting the use of the CuAAC reaction in biological systems is the copper-mediated formation of reactive oxygen species (ROS), leading to the oxidative degradation of proteins or peptides. From the studies on a limited number of proteins and peptides, it is known that, in general, the copper mediated oxidative damage is associated with the copper coordination environment and solvent accessibility. However, there is a lack of data to help estimate the extent of copper-mediated oxidation on a wide range of proteins and peptides. To begin to address this need, we quantitatively measured the degree of copper-mediated oxidation on libraries of 1200 tetrapeptides and a model protein (bovine serum albumin, BSA) using liquid chromatography mass spectrometry (LC-MS). The collected data will be useful to researchers planning to use the CuAAC reaction for bioconjugaton on peptides or proteins.
ISSN:1043-1802
1520-4812
DOI:10.1021/acs.bioconjchem.6b00267