N-THIOCARBONYL AZASUGARS - A NEW FAMILY OF CARBOHYDRATE MIMICS WITH CONTROLLED ANOMERIC CONFIGURATION

Authors
BIANCO JLJ PEREZ VMD MELLET CO FUENTES J FERNANDEZ JMG ARRIBAS JCD CANADA FJ
Citation
Jlj. Bianco et al., N-THIOCARBONYL AZASUGARS - A NEW FAMILY OF CARBOHYDRATE MIMICS WITH CONTROLLED ANOMERIC CONFIGURATION, Chemical communications, (20), 1997, pp. 1969-1970
Citations number
16
Categorie Soggetti
Chemistry
Journal title
Chemical communications → ACNP
ISSN journal
13597345
Issue
20
Year of publication
1997
Pages
1969 - 1970
Database
ISI
SICI code
1359-7345(1997):20<1969:NA-ANF>2.0.ZU;2-R
Abstract
Bicyclic azasugar glycomimetics structurally related to the polyhydrox y-indolizine and -piperidine series incorporating a stereoelectronical ly controlled pseudoanomeric axial hydroxy group have been prepared by tautomeric rearrangement of cyclic thiocarbamate precursors; prelimin ary enzyme inhibition tests show an increased selectivity towards yeas t alpha-glucosidase for the alpha-D-glucopyranose analogue as compared with castanospermine or nojirimicin.