Traceless and Chemoselective Amine Bioconjugation via Phthalimidine Formation in Native Protein Modification

Chun Ling Tung, Clarence T.T. Wong, Eva Yi Man Fung, Xuechen Li

Research output: Journal article publicationJournal articleAcademic researchpeer-review

45 Citations (Scopus)

Abstract

ortho-Phthalaldehyde (OPA) and its derivatives are found to react chemoselectively with amino groups on peptides and proteins rapidly and tracelessly under the physiological condition via formation of phthalimidines, which provides a novel and promising approach when performing bioconjugation on native proteins. The notable advantages of this method over the existing native protein lysine-labeling approaches include a traceless process, a self-reacting, specific and fast reaction, ease of operation, and the ability to use nonhydrolyzable reagents. Its applications have been effectively demonstrated including conjugation of peptides and proteins, and generation of an active PEGlyated l-asparaginase.

Original languageEnglish
Pages (from-to)2600-2603
Number of pages4
JournalOrganic Letters
Volume18
Issue number11
DOIs
Publication statusPublished - 3 Jun 2016
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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