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-β- d-galactopyranoside ( 1a,b), 4-nitrophenyl 7-deoxy- d- and l- glycero-β- d- galacto-heptopyranoside ( 2a,b) and 4-nitrophenyl 6,7-anhydro- d- and l- glycero-β- d- galacto-heptopyranoside...

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Bibliographic Details
Published in:Carbohydrate research 1997-12, Vol.305 (3), p.351-361
Main Authors: Grabowska, Urszula, MacManus, David A., Biggadike, Keith, Bird, Mike I., Davies, Stephen, Gallagher, Timothy, Hall, Lee D., Vulfson, Evgeny N.
Format: Article
Language:English
Subjects:
Chromatography, High Pressure Liquid
Diastereoselectivity
Enzymes
Galactosides - chemical synthesis
Galactosides - metabolism
Glycosidase
Glycoside Hydrolases - metabolism
Glycosides - isolation & purification
Kinetics
Molecular Structure
Resolution
Stereoisomerism
Transglycosylation
Unnatural glycosides
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Summary:The diastereoselectivity of the enzymatic hydrolyses of 4-nitrophenyl 6-deoxy-6-methyl-( R)- and ( S)-sulfinyl-β- d-galactopyranoside ( 1a,b), 4-nitrophenyl 7-deoxy- d- and l- glycero-β- d- galacto-heptopyranoside ( 2a,b) and 4-nitrophenyl 6,7-anhydro- d- and l- glycero-β- 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. The enzymatic resolution of diastereomeric β- d-galactosides incorporating a variety of stereogenic centres at the 6-position is described.
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(97)00246-2