Stereochemical characterisation of the non-canonical α-humulene synthase from Acremonium strictum

The non-canonical fungal alpha-humulene synthase was investigated through isotopic labelling experiments for its stereochemical course regarding inversion or retention at C-1, the face selectivity at C-11, and the stereoselectivity of the final deprotonation. A new and convenient desymmetrisation strategy was developed to enable a full stereochemical analysis of the catalysed steps to the achiral alpha-humulene product from stereoselectively labelled farnesyl diphosphate.

Automated summary

The non-canonical fungal alpha-humulene synthase was studied in terms of its stereochemical processes with isotopic labelling experiments. A new desymmetrisation strategy was developed to allow for a full stereochemical analysis from stereoselectively labelled farnesyl diphosphate to the achiral alpha-humulene product.