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 ((18)O)phenolic oxygen was incorporated, suggesting that phenol behaves as a nucleophile during the formation of the bent aryl ether.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acremonium / metabolism
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Biosynthetic Pathways
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Chromatography, High Pressure Liquid
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Crystallography, X-Ray
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Cyclization
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Heterocyclic Compounds, 4 or More Rings / chemistry
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Isotope Labeling*
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Mass Spectrometry
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Piperidines / chemistry*
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Polycyclic Compounds / chemistry*
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Pyrrolidinones / chemistry
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Stereoisomerism
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Tyrosine / chemical synthesis
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Tyrosine / chemistry
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Tyrosine / metabolism*
Substances
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GKK1032A-2
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Heterocyclic Compounds, 4 or More Rings
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Piperidines
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Polycyclic Compounds
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Pyrrolidinones
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Tyrosine