Abstract
The chemoenzymatic synthesis of three 1-deoxynojirimycin-type iminosugars is reported. Key steps in the synthetic scheme include a Dibal reduction-transimination-sodium borohydride reduction cascade of reactions on an enantiomerically pure cyanohydrin, itself prepared employing almond hydroxynitrile lyase (paHNL) as the common precursor. Ensuing ring-closing metathesis and Upjohn dihydroxylation afford the target compounds.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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1-Deoxynojirimycin / analogs & derivatives
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1-Deoxynojirimycin / chemical synthesis*
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1-Deoxynojirimycin / chemistry
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Aldehyde-Lyases / metabolism
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Cyclization
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Molecular Structure
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Nitriles / chemistry*
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Prunus / enzymology
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Stereoisomerism
Substances
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D-allo-1-deoxynojirimycin
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D-galacto-1-deoxynojirimycin
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L-altro-1-deoxynojirimycin
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Nitriles
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cyanohydrin
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1-Deoxynojirimycin
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Aldehyde-Lyases
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acetone-cyanohydrin lyase