Abstract
A straightforward chemo-enzymatic synthesis of new polyhydroxylated benzopyrrolizidines and cyclohexapyrrolizidines is developed. The two-step strategy consists of l-fuculose-1-phosphate aldolase variant F131A-catalyzed aldol addition of dihydroxyacetone phosphate to rac-N-benzyloxycarbonylindoline-2-carbaldehyde as well as (2S*,3aS*,7aS*)- and (2S*,3aR*,7aR*)-N-benzyloxycarbonyloctahydroindole-2-carbaldehydes and a subsequent one-step catalytic deprotection-reductive amination.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehyde-Lyases / metabolism
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Aldehydes / chemistry
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Amination
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Catalysis
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Cyclitols / chemical synthesis*
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Cyclitols / chemistry
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Cyclitols / pharmacology
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Dihydroxyacetone Phosphate / chemistry
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Fructose-Bisphosphate Aldolase / metabolism*
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Glycoside Hydrolases / metabolism
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Heterocyclic Compounds, 3-Ring / chemical synthesis*
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Heterocyclic Compounds, 3-Ring / chemistry
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Heterocyclic Compounds, 3-Ring / pharmacology
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Models, Molecular
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Molecular Structure
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Stereoisomerism
Substances
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Aldehydes
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Cyclitols
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Heterocyclic Compounds, 3-Ring
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Dihydroxyacetone Phosphate
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3-hydroxybutanal
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Glycoside Hydrolases
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Aldehyde-Lyases
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Fructose-Bisphosphate Aldolase
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L-fuculosephosphate aldolase