Category Archives: Simon Lanceron

An Expeditious Route to Fluorinated Rapamycin Analogues by Utilising Mutasynthesis

Rebecca J. M. Goss ; Simon Lanceron ; Abhijeet Deb Roy ; Simon Sprague ; Mohammed Nur-e-Alam ; David L. Hughes ; Barrie Wilkinson ; Steven J. Moss

ChemBioChem 2010, 11 (5) 698-702

Rapamycin is a drug with several important clinical uses. Its complex structure means that total synthesis of this natural product and its analogues is demanding and lengthy. A more expeditious approach is to utilise biosynthesis to enable the generation of otherwise synthetically intractable analogues. In order to achieve this, rules governing biosynthetic precursor substrate preference must be established. Through determining these rules and synthesising and administering suitable substrate precursors, we demonstrate the first generation of fluorinated rapamycin analogues. Here we report the generation of six new fluororapamycins.

Generating rapamycin analogues by directed biosynthesis: starter acid substrate specificity of mono-substituted cyclohexane carboxylic acids

Rebecca J. M. Goss ; Simon E. Lanceron ; Nicola J. Wise ; Steven J. Moss

Org Biomol Chem 2006, 4, 4071-4073

We report a convenient synthesis of 4-fluorocyclohexanoic acid, and an insight into the rules governing acceptance of starter acid analogues in the precursor-directed biosynthesis of rapamycin.

Graphical abstract: Generating rapamycin analogues by directed biosynthesis: starter acid substrate specificity of mono-substituted cyclohexane carboxylic acids