A one-pot enzymatic approach to the O-fluoroglucoside of N-methylanthranilate

Bioorg Med Chem. 2013 Aug 15;21(16):4762-7. doi: 10.1016/j.bmc.2013.05.057. Epub 2013 Jun 5.

Abstract

In connection with prospective (18)F-PET imaging studies, the potential for enzymatic synthesis of fluorine-labelled glycosides of small molecules was investigated. Approaches to the enzymatic synthesis of anomeric phosphates of d-gluco-configured fluorosugars proved ineffective. In contrast, starting in the d-galacto series and relying on the consecutive action of Escherichia coli galactokinase (GalK), galactose-1-phosphate uridylyltransferase (GalPUT), uridine-5'-diphosphogalactose 4-epimerase (GalE) and oat root glucosyltransferase (SAD10), a quick and effective synthesis of 6-deoxy-6-fluoro-d-glucosyl N-methylanthranilate ester was achieved.

Keywords: Biotransformation; Fluorosugar; Glucosyltransferase; Natural product; Sugar nucleotide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Avena / enzymology
  • Escherichia coli / enzymology
  • Escherichia coli Proteins / metabolism*
  • Galactokinase / metabolism*
  • Glucosides / chemistry*
  • Glucosides / metabolism
  • Glucosyltransferases / metabolism*
  • Plant Proteins / metabolism*
  • UTP-Hexose-1-Phosphate Uridylyltransferase / metabolism*
  • ortho-Aminobenzoates / chemistry*
  • ortho-Aminobenzoates / metabolism*

Substances

  • 6-deoxy-6-fluoro-D-glucosyl N-methylanthranilate ester
  • Escherichia coli Proteins
  • Glucosides
  • Plant Proteins
  • ortho-Aminobenzoates
  • anthranilic acid
  • Glucosyltransferases
  • Galactokinase
  • UTP-Hexose-1-Phosphate Uridylyltransferase