Palladium-Mediated Cleavage of Proteins with Thiazolidine-Modified Backbone in Live Cells

Guy Mann, Gandhesiri Satish, Roman Meledin, Ganga B. Vamisetti, Ashraf Brik

Research output: Contribution to journalReview articlepeer-review

46 Scopus citations

Abstract

Chemical protein synthesis and biorthogonal modification chemistries allow production of unique proteins for a range of biological studies. Bond-forming reactions for site-selective protein labeling are commonly used in these endeavors. Selective bond-cleavage reactions, however, are much less explored and still pose a great challenge. In addition, most of studies with modified proteins prepared by either total synthesis or semisynthesis have been applied mainly for in vitro experiments with very limited extension to live cells. Reported here is an approach for studying uniquely modified proteins containing a traceless cell delivery unit and palladium-based cleavable element for chemical activation, and monitoring the effect of these proteins in live cells. This approach is demonstrated for the synthesis of a caged ubiquitin-aldehyde, which was decaged for the inhibition of deubiquitinases in live cells.

Original languageEnglish
Pages (from-to)13540-13549
Number of pages10
JournalAngewandte Chemie - International Edition
Volume58
Issue number38
DOIs
StatePublished - 16 Sep 2019
Externally publishedYes

Keywords

  • cells
  • fluorescence
  • inhibitors
  • palladium
  • proteins

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

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