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

Houchao Xu,C. Schotte,Russell John Cox,Jeroen S. Dickschat

Published 2021 in Organic and biomolecular chemistry

ABSTRACT

The non-canonical fungal α-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 α-humulene product from stereoselectively labelled farnesyl diphosphate.

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