A Palette of Minimally Tagged Sucrose Analogues for Real-Time Raman Imaging of Intracellular Plant Metabolism

Angew Chem Int Ed Engl. 2021 Mar 29;60(14):7637-7642. doi: 10.1002/anie.202016802. Epub 2021 Feb 26.

Abstract

Sucrose is the main saccharide used for long-distance transport in plants and plays an essential role in energy metabolism; however, there are no analogues for real-time imaging in live cells. We have optimised a synthetic approach to prepare sucrose analogues including very small (≈50 Da or less) Raman tags in the fructose moiety. Spectroscopic analysis identified the alkyne-tagged compound 6 as a sucrose analogue recognised by endogenous transporters in live cells and with higher Raman intensity than other sucrose derivatives. Herein, we demonstrate the application of compound 6 as the first optical probe to visualise real-time uptake and intracellular localisation of sucrose in live plant cells using Raman microscopy.

Keywords: imaging; probes; stimulated Raman scattering; sugars; transport.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkynes / chemistry
  • Azides / chemistry*
  • Cell Membrane Permeability
  • Coumarins / chemistry*
  • Indicators and Reagents / chemistry*
  • Kinetics
  • Membrane Transport Proteins / chemistry*
  • Membrane Transport Proteins / genetics
  • Metabolome
  • Microscopy
  • Plant Cells / metabolism*
  • Plant Proteins / chemistry*
  • Plant Proteins / genetics
  • Spectrum Analysis, Raman
  • Sucrose / analysis*
  • Sucrose / metabolism*
  • Yeasts / genetics

Substances

  • 3-azido-7-hydroxycoumarin
  • Alkynes
  • Azides
  • Coumarins
  • Indicators and Reagents
  • Membrane Transport Proteins
  • Plant Proteins
  • sucrose transport protein, plant
  • Sucrose