Abstract
The naturally occurring sugar mimetic alkaloids 1-deoxymannojirimycin (DMJ, 1) and 6-O-alpha-L-rhamnopyranosyl-DMJ (2) have each been prepared in a completely stereoselective manner from the cis-1,2-dihydrocatechol 3, itself obtained in enantiomerically pure form by microbial oxidation of chlorobenzene.
MeSH terms
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1-Deoxynojirimycin / chemical synthesis*
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1-Deoxynojirimycin / pharmacology
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Animals
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Catechols / chemistry
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Cattle
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Chlorobenzenes / chemistry
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Chlorobenzenes / metabolism
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Enzyme Inhibitors / chemical synthesis
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Enzyme Inhibitors / pharmacology
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Glycoside Hydrolases / antagonists & inhibitors
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Glycosides / chemical synthesis*
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Glycosides / chemistry
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Glycosides / pharmacology
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Humans
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Oxidation-Reduction
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Rats
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Rhamnose / analogs & derivatives
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Rhamnose / chemical synthesis
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Rhamnose / pharmacology
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Stereoisomerism
Substances
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Catechols
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Chlorobenzenes
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Enzyme Inhibitors
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Glycosides
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1-Deoxynojirimycin
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Glycoside Hydrolases
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Rhamnose