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

Lorenzo Caputi, Martin Rejzek, Thomas Louveau, Ellis C. O’Neill, Lionel Hill, Anne Osbourn and Robert A. Field

Résumé:

In connection with prospective ¹⁸F-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.

Revue:

Bioorganic & Medicinal Chemistry

Lien:

https://www.sciencedirect.com/science/article/pii/S0968089613005063