Jump to main content
Jump to site search

Issue 12, 2015
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 19 Jan 2015, accepted on 02 Feb 2015 and first published on 02 Feb 2015


Article type: Paper
DOI: 10.1039/C5OB00114E
Author version
available:
Download author version (PDF)
Org. Biomol. Chem., 2015,13, 3662-3666

  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements