title: Diastereoselective resolution of 6-substituted glycosides via enzymatic hydrolysis.
abstract: The diastereoselectivity of the enzymatic hydrolyses of 4-nitrophenyl 6-deoxy-6-methyl-(R)- and (S)-sulfinyl-beta-D-galactopyranoside (1a,b), 4-nitrophenyl 7-deoxy-D- and L-glycero-beta-D-galacto-heptopyranoside (2a,b) and 4-nitrophenyl 6,7-anhydro-D- and L-glycero-beta-D-galacto-heptopyranoside (3a,b) was investigated using a range of crude glycosidase preparations. It was shown that the enzymes display a high degree of discrimination between diastereomers thereby demonstrating the utility of glycosidases for the diastereomeric resolution of unnatural 6-substituted monosaccharide derivatives.
authors.affiliation: GlaxoWellcome, Medicines Research Centre, Stevenage, UK.
authors.forename: U
authors.initials: U
authors.lastname: Grabowska
authors.forename: D A
authors.initials: DA
authors.lastname: MacManus
authors.forename: K
authors.initials: K
authors.lastname: Biggadike
authors.forename: M I
authors.initials: MI
authors.lastname: Bird
authors.forename: S
authors.initials: S
authors.lastname: Davies
authors.forename: T
authors.initials: T
authors.lastname: Gallagher
authors.forename: L D
authors.initials: LD
authors.lastname: Hall
authors.forename: E N
authors.initials: EN
authors.lastname: Vulfson
mesh_terms: D002851:Chromatography, High Pressure Liquid; D005697:Galactosides / Q000138:chemical synthesis / Q000378:metabolism; D006026:Glycoside Hydrolases / Q000378:metabolism*; D006027:Glycosides / Q000302:isolation & purification*; D007700:Kinetics; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D005697:Galactosides; D006027:Glycosides; D006026:Glycoside Hydrolases