Fluorinated tropane alkaloids generated by directed biosynthesis in transformed root cultures of Datura stramonium

Abstract

2′-, 3′- and 4′-Fluorophenyl-(RS)-lactic acids were administered to transformed root cultures of Datura stramonium to determine their abilities as substrates for incorporation into the phenyllactoyl and tropoyl ester moieties of the tropane alkaloids, littorine and hyoscyamine respectively. In the event, all of the fluorinated phenyllactates generated the corresponding fluorinated littorine and hyoscyamine analogues. The efficiency of conversion for the isomerisation of the fluorinated littorines (F-lit) to fluorinated hyoscyamines was 3′-F-lit > 4′-F-lit 2′-F-lit.