An expedient enzymatic route to isomeric 2-, 3- and 6-monodeoxy-monofluoro-maltose derivatives

Carbohydr Res. 2012 Sep 1:358:12-8. doi: 10.1016/j.carres.2012.05.026. Epub 2012 Jun 7.

Abstract

2-Deoxy-2-fluoro-d-glucose, 3-deoxy-3-fluoro-D-glucose and 6-deoxy-6-fluoro-D-glucose were converted into the corresponding maltose derivatives using Arabidopsis thaliana DPE2-mediated trans-glycosylation reaction with glycogen acting as a glucosyl donor. (19)F NMR spectroscopy proved to be a valuable tool for monitoring the progress of these reactions and to assess the nature of resulting oligomeric products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Arabidopsis / enzymology
  • Arabidopsis Proteins / metabolism
  • Deoxyglucose / analogs & derivatives*
  • Deoxyglucose / chemistry
  • Deoxyglucose / metabolism
  • Fluorodeoxyglucose F18 / chemistry
  • Fluorodeoxyglucose F18 / metabolism*
  • Glycogen / chemistry
  • Glycogen / metabolism
  • Glycoside Hydrolases / metabolism
  • Glycosylation
  • Magnetic Resonance Spectroscopy
  • Maltose / chemical synthesis
  • Maltose / chemistry*
  • Maltose / metabolism*

Substances

  • Arabidopsis Proteins
  • Fluorodeoxyglucose F18
  • 3-deoxy-3-fluoro-D-glucose
  • 6-deoxy-6-fluoroglucose
  • Maltose
  • Glycogen
  • Deoxyglucose
  • Glycoside Hydrolases