Functionalized quinolizinium-based fluorescent reagents for modification of cysteine-containing peptides and proteins

Karen Ka Yan Kung, Cai Fung Xu, O. Wa-Yi, Qiong Yu, Sai Fung Chung, Suet Ying Tam, Yun Chung Leung, Man Kin Wong

Research output: Journal article publicationJournal articleAcademic researchpeer-review

Abstract

A series of quinolizinium-based fluorescent reagents were prepared by visible light-mediated goldcatalyzed cis-difunctionalization between quinolinium diazonium salts and electron-deficient alkynelinked phenylethynyl trimethylsilanes. The electron-deficient alkynyl group of the quinolizinium-based fluorescent reagents underwent nucleophilic addition reaction with the sulfhydryl group on cysteinecontaining peptides and proteins. The quinolizinium-based fluorescent reagents were found to function as highly selective reagents for the modification of cysteine-containing peptides and proteins with good to excellent conversions (up to 99%). Moreover, the modified BCArg mutants bearing cationic quinolizinium compounds 1b, 1d, 1e and 1h exhibit comparable activity in enzymatic and cytotoxicity assays to the unmodified one.

Original languageEnglish
Pages (from-to)6248-6254
Number of pages7
JournalRSC Advances
Volume12
Issue number10
DOIs
Publication statusPublished - 22 Feb 2022

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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