Abstract
The trans-decalin structure formed by intramolecular Diels-Alder cycloaddition is widely present among bioactive natural products isolated from fungi. We elucidated the concise three-enzyme biosynthetic pathway of the cytotoxic myceliothermophin and biochemically characterized the Diels-Alderase that catalyzes the formation of trans-decalin from an acyclic substrate. Computational studies of the reaction mechanism rationalize both the substrate and stereoselectivity of the enzyme.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Biocatalysis
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Cycloaddition Reaction
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Eukaryota / chemistry*
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Eukaryota / metabolism
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Euryarchaeota / enzymology
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Naphthalenes / chemistry
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Naphthalenes / metabolism*
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Peptide Synthases / chemistry
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Peptide Synthases / metabolism*
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Polyketide Synthases / chemistry
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Polyketide Synthases / metabolism*
Substances
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Naphthalenes
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Polyketide Synthases
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decalin
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Peptide Synthases
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non-ribosomal peptide synthase