Abstract
A straightforward chemoenzymatic synthesis of four uncovered casuarine stereoisomers is described. The strategy consists of L-fuculose-1-phosphate aldolase F131A-variant-catalyzed aldol addition of dihydroxyacetone phosphate to aldehyde derivatives of 1,4-dideoxy-1,4-imino-D-arabinitol (DAB) and its enantiomer (LAB) and subsequent one-pot catalytic deprotection-reductive amination. DAB and LAB were obtained from dihydroxyacetone and aminoethanol using D-fructose-6-phosphate aldolase and L-rhamnulose-1-phosphate aldolase catalysts, respectively. The new ent-3-epi-casuarine is a strong inhibitor of α-d-glucosidase from rice and of rat intestinal sucrase.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehyde-Lyases / antagonists & inhibitors*
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Aldehyde-Lyases / chemistry*
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Alkaloids / chemical synthesis*
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Alkaloids / chemistry
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Alkaloids / pharmacology*
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Animals
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Arabinose / chemistry*
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Dihydroxyacetone Phosphate / chemistry*
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / pharmacology*
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Ethanolamine / chemistry*
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Fructose-Bisphosphate Aldolase / antagonists & inhibitors*
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Fructose-Bisphosphate Aldolase / chemistry
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Glycoside Hydrolase Inhibitors / chemical synthesis*
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Glycoside Hydrolase Inhibitors / chemistry
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Glycoside Hydrolase Inhibitors / pharmacology*
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Imino Furanoses / chemistry*
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Molecular Structure
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Oryza / chemistry*
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Pyrroles / chemical synthesis*
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Pyrroles / chemistry
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Pyrroles / pharmacology*
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Rats
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Stereoisomerism
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Sucrase / antagonists & inhibitors*
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Sucrase / chemistry*
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Sugar Alcohols / chemistry*
Substances
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Alkaloids
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Enzyme Inhibitors
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Glycoside Hydrolase Inhibitors
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Imino Furanoses
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Pyrroles
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Sugar Alcohols
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casuarine
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1,4-dideoxy-1,4-iminoarabinitol
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Dihydroxyacetone Phosphate
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Ethanolamine
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Arabinose
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Sucrase
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Aldehyde-Lyases
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Fructose-Bisphosphate Aldolase
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L-fuculosephosphate aldolase
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rhamnulose-1-phosphate adolase