Combining Wittig Olefination with Photoassisted Domino Reaction To Distinguish 5-Formylcytosine from 5-Formyluracil

Anal Chem. 2019 Aug 6;91(15):9366-9370. doi: 10.1021/acs.analchem.9b02499. Epub 2019 Jul 23.

Abstract

In view of the important epigenetic functions of 5-formylcytosine (5fC), the development of quantitative detection methods for 5fC is a long-standing issue. In this regard, how to distinguish 5fC from 5-formyluracil to achieve higher accuracy is particularly difficult because the latter one is more reactive. Herein, we reported a phosphorus ylide, YC-CN, and introduced a triple domino reaction to fluorescently switch on 5fC with excellent selectivity, which also enable us to quantify 5fC mutations induced by γ-irradiation. This Wittig-initiated covalent labeling strategy provide a novel strategy for qualitative and quantitative detection of 5fC.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cytosine / analogs & derivatives*
  • Cytosine / analysis
  • Epigenomics
  • Fluorescence
  • Gamma Rays / adverse effects
  • Mutation / radiation effects
  • Uracil / analogs & derivatives
  • Uracil / analysis

Substances

  • 5-formylcytosine
  • 5-formyluracil
  • Uracil
  • Cytosine