Issue 12, 2015

Direct biosynthetic cyclization of a distorted paracyclophane highlighted by double isotopic labelling of l-tyrosine

Abstract

The biosynthesis of pyrrocidines, fungal PK-NRP compounds featuring a strained [9]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.

Graphical abstract: Direct biosynthetic cyclization of a distorted paracyclophane highlighted by double isotopic labelling of l-tyrosine

Supplementary files

Article information

Article type
Paper
Submitted
19 Jan 2015
Accepted
02 Feb 2015
First published
02 Feb 2015

Org. Biomol. Chem., 2015,13, 3662-3666

Author version available

Direct biosynthetic cyclization of a distorted paracyclophane highlighted by double isotopic labelling of L-tyrosine

A. Ear, S. Amand, F. Blanchard, A. Blond, L. Dubost, D. Buisson and B. Nay, Org. Biomol. Chem., 2015, 13, 3662 DOI: 10.1039/C5OB00114E

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