Synthesis of the enantiomers of 6-epicastanospermine and 1,6-diepicastanospermine from d- and l-gulonolactone

The synthesis of the enantiomers of 6-epicastanospermine and of 1,6-diepicastanospermine from the enantiomeric gulonolactones is reported and the structure of the former is established as (1 S,6 R,7 R,8 R,8a R)-1,6,7,8-tetrahydroxyoctahydroindolizine. The inhibitory activities of the diastereomers a...

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Bibliographic Details
Published in:Carbohydrate research 1990-09, Vol.205, p.269-282
Main Authors: Fleet, George W.J., Ramsden, Nigel G., Nash, Robert J., Fellows, Linda E., Jacob, Gary S., Molyneux, Russell J., di Bello, Isabelle Cenci, Winchester, Bryan
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Glycoside Hydrolases - antagonists & inhibitors
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Humans
In Vitro Techniques
Indolizines - chemical synthesis
Indolizines - chemistry
Indolizines - pharmacology
Liver - enzymology
Magnetic Resonance Spectroscopy
Molecular Structure
Organic chemistry
Preparations and properties
Stereoisomerism
Sugar Acids
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Summary:The synthesis of the enantiomers of 6-epicastanospermine and of 1,6-diepicastanospermine from the enantiomeric gulonolactones is reported and the structure of the former is established as (1 S,6 R,7 R,8 R,8a R)-1,6,7,8-tetrahydroxyoctahydroindolizine. The inhibitory activities of the diastereomers against the amyloglucosidase-catalysed hydrolysis of p-nitrophenyl α- d-glucopyranoside were investigated, and the effects of 6-epicastanospermine and of 1,6-diepicastanospermine on 14 human liver glycosidases are reported.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(90)80146-T