Application of meta- and para-phenylenediamine as enhanced oxime ligation catalysts for protein labeling, PEGylation, immobilization, and release

Mohammad M. Mahmoodi, Mohammad Rashidian, Yi Zhang, Mark D. Distefano

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)15.4.1-15.4.28
JournalCurrent Protocols in Protein Science
Volume2015
DOIs
StatePublished - 2015

Keywords

  • Dual protein labeling
  • Hydrazone ligation
  • Meta-phenylenediamine
  • Oxime ligation
  • Para-phenylenediamine

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