Application of meta‐ and para‐Phenylenediamine as Enhanced Oxime Ligation Catalysts for Protein Labeling, PEGylation, Immobilization, and Release. (2nd February 2015)

• Record Type: Journal Article
• Authors: Mahmoodi, Mohammad M.; Rashidian, Mohammad; Zhang, Yi; Distefano, Mark D.
• Editors: Coligan, John E.; Dunn, Ben M.; Speicher, David W.; Wingfield, Paul T.
• Is Part Of: Current protocols in protein science. Volume 79(2015)
• Page Start: 15.4.1
• Page End: 15.4.28
• Publication Date: 2015-02-02
• Subjects: oxime ligation -- hydrazone ligation -- meta‐phenylenediamine -- para‐phenylenediamine -- dual protein labeling; Proteins -- Laboratory manuals; Proteins; Clinical Laboratory Techniques; Genetic Techniques; Immunologic Techniques; Proteins; Laboratory manuals; 572.6028
• DOI: 10.1002/0471140864.ps1504s79
• Languages: English
• ISSNs: 1934-3655

Abstract

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. © 2015 by John Wiley & Sons, Inc.