A general method for the preparation of galactose derivatives locked in a <sup>1,4</sup>B boat conformation has been developed. The boat scaffold was stereoselectively functionalized at the C-1′ position by aliphatic and aromatic groups along with azido or hydroxy groups. The configuration at the new stereogenic center was controlled and determined by X-raydiffraction. These molecules were designed to probe the conformational itinerary of the substrate of glycosyl hydrolases. Inhibition assays were performed against a series of commercially available glycosidases, which showed that these enzymes do not harness a <sup>1,4</sup>B-boat-like transition state.
- Conformation analysis
FingerprintDive into the research topics of 'Stereoselective synthesis of boat-locked glycosides designed as glycosyl hydrolase conformational probes'. Together they form a unique fingerprint.
Technological Platform Physical Chemistry and characterization
Facility/equipment: Technological Platform