title: Application of meta- and para-Phenylenediamine as Enhanced Oxime Ligation Catalysts for Protein Labeling, PEGylation, Immobilization, and Release.
abstract: Meta- and para-phenylenediamines have recently been shown to catalyze oxime and hydrazone ligation reactions at rates much faster than aniline, a commonly used catalyst. Here, we demonstrate how these new catalysts can be used in a generally applicable procedure for fluorescent labeling, PEGylation, immobilization, and release of aldehyde- and ketone- functionalized proteins. The chemical orthogonality of phenylenediamine-catalyzed oxime ligation versus copper-catalyzed click reaction has also been harnessed for simultaneous dual labeling of bifunctional proteins containing both aldehyde and alkyne groups in high yield.
authors: Department of Chemistry, University of Minnesota, Minneapolis, Minnesota.
authors: Mohammad M
authors: MM
authors: Mahmoodi
authors: Department of Chemistry, University of Minnesota, Minneapolis, Minnesota.
authors: Mohammad
authors: M
authors: Rashidian
authors: Department of Chemistry, University of Minnesota, Minneapolis, Minnesota.
authors: Yi
authors: Y
authors: Zhang
authors: Department of Chemistry, University of Minnesota, Minneapolis, Minnesota.
authors: Mark D
authors: MD
authors: Distefano
mesh_terms: D001671:Biochemistry; D002384:Catalysis; D006835:Hydrazones / Q000737:chemistry; D055767:Immobilized Proteins / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D010091:Oximes / Q000737:chemistry*; D010655:Phenylenediamines / Q000737:chemistry*; D011092:Polyethylene Glycols / Q000737:chemistry*
chemical_list: D006835:Hydrazones; D055767:Immobilized Proteins; D007202:Indicators and Reagents; D010091:Oximes; D010655:Phenylenediamines; D011092:Polyethylene Glycols; C008381:3-phenylenediamine; C029728:4-phenylenediamine
keywords: dual protein labeling; hydrazone ligation; meta-phenylenediamine; oxime ligation; para-phenylenediamine
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