Abstract
Hirsutellones are fungal natural products containing a macrocyclic para-cyclophane connected to a decahydrofluorene ring system. We have elucidated the biosynthetic pathway for pyrrocidine B (3) and GKK1032 A2 (4). Two small hypothetical proteins, an oxidoreductase and a lipocalin-like protein, function cooperatively in the oxidative cyclization of the cyclophane, while an additional hypothetical protein in the pyrrocidine pathway catalyzes the exo-specific cycloaddition to form the cis-fused decahydrofluorene.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Acremonium / chemistry
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Acremonium / metabolism
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Biological Products / chemistry
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Biological Products / metabolism*
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Bridged-Ring Compounds / chemistry
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Bridged-Ring Compounds / metabolism*
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Catalysis
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Cycloaddition Reaction
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Fungi / chemistry*
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Fungi / metabolism
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Heterocyclic Compounds, 4 or More Rings / chemistry
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Heterocyclic Compounds, 4 or More Rings / metabolism*
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Hypocreales / chemistry
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Hypocreales / metabolism
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Molecular Conformation
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Oxidation-Reduction
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Oxidoreductases / metabolism
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Pyrrolidinones / chemistry
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Pyrrolidinones / metabolism*
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Stereoisomerism
Substances
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Biological Products
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Bridged-Ring Compounds
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GKK1032A-2
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Heterocyclic Compounds, 4 or More Rings
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Pyrrolidinones
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hirsutellone B
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pyrrocidine B
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Oxidoreductases