Diastereoselective resolution of 6-substituted glycosides via enzymatic hydrolysis.
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.
Grabowska
U
U
GlaxoWellcome, Medicines Research Centre, Stevenage, UK.
MacManus
D A
DA
Biggadike
K
K
Bird
M I
MI
Davies
S
S
Gallagher
T
T
Hall
L D
LD
Vulfson
E N
EN
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
D005697:Galactosides; D006027:Glycosides; D006026:Glycoside Hydrolases