1,5-Alpha-D-mannoseptanosides, ring-size isomers that are impervious to alpha-mannosidase-catalyzed hydrolysis

Matthew A Boone; Frank E McDonald; Joseph Lichter; Stefan Lutz; Rui Cao; Kenneth I Hardcastle

doi:10.1021/ol8028065

1,5-Alpha-D-mannoseptanosides, ring-size isomers that are impervious to alpha-mannosidase-catalyzed hydrolysis

Org Lett. 2009 Feb 19;11(4):851-4. doi: 10.1021/ol8028065.

Authors

Matthew A Boone¹, Frank E McDonald, Joseph Lichter, Stefan Lutz, Rui Cao, Kenneth I Hardcastle

Affiliation

¹ Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.

PMID: 19154123
DOI: 10.1021/ol8028065

Abstract

1,5-D-mannoseptanosyl di- and trisaccharide ring-size isomers of the corresponding mannopyranosyl oligosaccharides have been prepared. Remarkably, these compounds show no inhibition of the alpha-mannosidase-catalyzed hydrolysis of p-nitrophenyl-alpha-D-mannopyranoside.

Publication types

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

MeSH terms

Catalysis
Hydrolysis
Mannosides / chemical synthesis*
Mannosides / chemistry
Molecular Structure
Oligosaccharides / chemical synthesis*
Oligosaccharides / chemistry
Stereoisomerism
alpha-Mannosidase / metabolism*

Substances

Mannosides
Oligosaccharides
alpha-Mannosidase