Abstract
The NADPH-dependent tetrahydroxynaphthalene reductase (T4HNR) from Magnaporthe grisea was used for the biomimetic synthesis of (R)-GTRI-02 by stereoselective reduction of 1-(3,6,8-trihydroxy-1-methylnaphthalen-2-yl)ethanone. This also led to the isolation of a (3S,4R)-cis-ketodiol formed by T4HNR-catalyzed reduction of the corresponding hydroxynaphthoquinone. Flaviolin and lawsone also reduced to corresponding cis-ketodiols in good yields.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Atovaquone / chemistry*
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Biomimetics
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Fungal Proteins / chemistry*
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Molecular Structure
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Naphthalenes / chemical synthesis*
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Naphthalenes / chemistry
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Naphthols / chemical synthesis*
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Naphthols / chemistry*
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Oxidoreductases Acting on CH-CH Group Donors / chemistry*
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Stereoisomerism
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Tetrahydronaphthalenes / chemical synthesis*
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Tetrahydronaphthalenes / chemistry*
Substances
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1-(3,6,8-trihydroxy-1-methylnaphthalen-2-yl)ethanone
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Fungal Proteins
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GTRI 02
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Naphthalenes
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Naphthols
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Tetrahydronaphthalenes
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tetrahydroxynaphthalene reductase
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Oxidoreductases Acting on CH-CH Group Donors
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Atovaquone