Thiazolidin-5-imine Formation as a Catalyst-Free Bioorthogonal Reaction for Protein and Live Cell Labeling

Org Lett. 2018 Dec 21;20(24):7790-7793. doi: 10.1021/acs.orglett.8b03195. Epub 2018 Dec 5.

Abstract

A previously undescribed reaction involving the formation of a thiazolidin-5-imine linkage was developed for bioconjugation. Being highly specific and operating in aqueous media, this simple condensation reaction is used to chemoselectively label peptides, proteins, and living cells under physiological conditions without the need to use toxic catalysts or reducing reagents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • HeLa Cells
  • Humans
  • Imines / chemical synthesis
  • Imines / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Optical Imaging*
  • Proteins / analysis*
  • Staining and Labeling
  • Thiazolidines / chemical synthesis
  • Thiazolidines / chemistry*

Substances

  • Fluorescent Dyes
  • Imines
  • Proteins
  • Thiazolidines