4.6 Article

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

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ORGANIC & BIOMOLECULAR CHEMISTRY
卷 19, 期 39, 页码 8482-8486

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ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ob01769a

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  1. DFG [DI1536/7-2]

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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.
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.

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