title: Extent of the Oxidative Side Reactions to Peptides and Proteins During the CuAAC Reaction.
abstract: 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.
authors: Department of Chemistry and ‡Department of Biology and Biochemistry, University of Houston , 4800 Calhoun Road, Houston, Texas 77204, United States.
authors: Siheng
authors: S
authors: Li
authors: Department of Chemistry and ‡Department of Biology and Biochemistry, University of Houston , 4800 Calhoun Road, Houston, Texas 77204, United States.
authors: Honghao
authors: H
authors: Cai
authors: Department of Chemistry and ‡Department of Biology and Biochemistry, University of Houston , 4800 Calhoun Road, Houston, Texas 77204, United States.
authors: Jilin
authors: J
authors: He
authors: Department of Chemistry and ‡Department of Biology and Biochemistry, University of Houston , 4800 Calhoun Road, Houston, Texas 77204, United States.
authors: Haoqing
authors: H
authors: Chen
authors: Department of Chemistry and ‡Department of Biology and Biochemistry, University of Houston , 4800 Calhoun Road, Houston, Texas 77204, United States.
authors: Srujana
authors: S
authors: Lam
authors: Department of Chemistry and ‡Department of Biology and Biochemistry, University of Houston , 4800 Calhoun Road, Houston, Texas 77204, United States.
authors: Tao
authors: T
authors: Cai
authors: Department of Chemistry and ‡Department of Biology and Biochemistry, University of Houston , 4800 Calhoun Road, Houston, Texas 77204, United States.
authors: Zhiling
authors: Z
authors: Zhu
authors: Department of Chemistry and ‡Department of Biology and Biochemistry, University of Houston , 4800 Calhoun Road, Houston, Texas 77204, United States.
authors: Steven J
authors: SJ
authors: Bark
authors: Department of Chemistry and ‡Department of Biology and Biochemistry, University of Houston , 4800 Calhoun Road, Houston, Texas 77204, United States.
authors: Chengzhi
authors: C
authors: Cai
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000737:chemistry; D010084:Oxidation-Reduction; D019151:Peptide Library; D010455:Peptides / Q000737:chemistry*; D011506:Proteins / Q000737:chemistry*; D012710:Serum Albumin, Bovine / Q000737:chemistry
chemical_list: D000480:Alkynes; D001386:Azides; D016166:Free Radical Scavengers; D019151:Peptide Library; D010455:Peptides; D011506:Proteins; D012710:Serum Albumin, Bovine; D003300:Copper