Synthesis of the enantiomers of 6-epicastanospermine and 1,6-diepicastanospermine from D- and L-gulonolactone

G W Fleet; N G Ramsden; R J Nash; L E Fellows; G S Jacob; R J Molyneux; I C di Bello; B Winchester

doi:10.1016/0008-6215(90)80146-t

Synthesis of the enantiomers of 6-epicastanospermine and 1,6-diepicastanospermine from D- and L-gulonolactone

Carbohydr Res. 1990 Sep 19:205:269-82. doi: 10.1016/0008-6215(90)80146-t.

Authors

G W Fleet¹, N G Ramsden, R J Nash, L E Fellows, G S Jacob, R J Molyneux, I C di Bello, B Winchester

Affiliation

¹ Dyson Perrins Laboratory, Oxford University, Great Britain.

PMID: 2276139
DOI: 10.1016/0008-6215(90)80146-t

Abstract

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 (1S,6R,7R,8R,8aR)-1,6,7,8-tetrahydroxyoctahydroindolizine. The inhibitory activities of the diastereomers against the amyloglucosidase-catalysed hydrolysis of p-nitrophenyl alpha-D-glucopyranoside were investigated, and the effects of 6-epicastanospermine and of 1,6-diepicastanospermine on 14 human liver glycosidases are reported.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Glycoside Hydrolases / antagonists & inhibitors
Humans
In Vitro Techniques
Indolizines / chemical synthesis*
Indolizines / chemistry
Indolizines / pharmacology
Liver / enzymology
Magnetic Resonance Spectroscopy
Molecular Structure
Stereoisomerism
Sugar Acids

Substances

Indolizines
Sugar Acids
gulonolactone
Glycoside Hydrolases
castanospermine