An expedient enzymatic route to isomeric 2-, 3- and 6-monodeoxy-monofluoro-maltose derivatives

[Display omitted] ► Three GH77 glycosidases were assessed for glucosylation of fluoroglucose with a glycogen donor. ► Deoxy-fluoro-maltose derivatives were synthesised using Arabidopsis trans-glycosidase DPE2. ► 19F NMR spectroscopy proved useful for following trans-glycosylation reactions of fluoro...

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Bibliographic Details
Published in:Carbohydrate research 2012-09, Vol.358, p.12-18
Main Authors: Tantanarat, Krit, Rejzek, Martin, O’Neill, Ellis, Ruzanski, Christian, Hill, Lionel, Fairhurst, Shirley A., Limpaseni, Tipaporn, Field, Robert A.
Format: Article
Language:English
Subjects:
19F NMR spectroscopy
Arabidopsis - enzymology
Arabidopsis Proteins - metabolism
Arabidopsis thaliana
Deoxyglucose - analogs & derivatives
Deoxyglucose - chemistry
Deoxyglucose - metabolism
Fluorodeoxyglucose F18 - chemistry
Fluorodeoxyglucose F18 - metabolism
Fluoroglucose
Fluoromaltose
Glycogen
Glycogen - chemistry
Glycogen - metabolism
Glycoside Hydrolases - metabolism
Glycosylation
Magnetic Resonance Spectroscopy
maltose
Maltose - chemical synthesis
Maltose - chemistry
Maltose - metabolism
monitoring
nuclear magnetic resonance spectroscopy
trans-Glycosylation
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Summary:[Display omitted] ► Three GH77 glycosidases were assessed for glucosylation of fluoroglucose with a glycogen donor. ► Deoxy-fluoro-maltose derivatives were synthesised using Arabidopsis trans-glycosidase DPE2. ► 19F NMR spectroscopy proved useful for following trans-glycosylation reactions of fluorosugars. 2-Deoxy-2-fluoro-d-glucose, 3-deoxy-3-fluoro-d-glucose and 6-deoxy-6-fluoro-d-glucose were converted into the corresponding maltose derivatives using Arabidopsis thaliana DPE2-mediated trans-glycosylation reaction with glycogen acting as a glucosyl donor. 19F NMR spectroscopy proved to be a valuable tool for monitoring the progress of these reactions and to assess the nature of resulting oligomeric products.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2012.05.026