Direct biosynthetic cyclization of a distorted paracyclophane highlighted by double isotopic labelling of l-tyrosine†
The biosynthesis of pyrrocidines, fungal PK-NRP compounds featuring a strained paracyclophane, was investigated in Acremonium zeae. We used a synthetic L-tyrosine probe, labelled with oxygen 18 as a reporter of phenol reactivity and carbon 13 as a tracer of incorporation of this exogenous precursor. The (18O)phenolic oxygen was incorporated, suggesting that phenol behaves as a nucleophile during the formation of the bent aryl ether.
- This article is part of the themed collections: 2015 Hot Articles in Organic and Biomolecular Chemistry and Natural Products in Organic & Biomolecular Chemistry