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Type: Journal article
Title: The synthesis of 3-O-(beta-D-glucopyranosyl)- and 3-O-(beta-laminaribiosyl)-isofagomines, potent inhibitors of a 1,3-beta-D-glucan endo-hydrolase
Author: Macdonald, J.
Hrmova, M.
Fincher, G.
Stick, R.
Citation: Australian Journal of Chemistry, 2004; 57(3):187-191
Publisher: C S I R O Publishing
Issue Date: 2004
ISSN: 0004-9425
Statement of
James M. Macdonald, Maria Hrmova, Geoffrey B. Fincher and Robert V. Stick
Abstract: The glycosylation of 4,6-O-benzylidene-N-benzyloxycarbonylisofagomine with a D-glucosyl and a laminari-biosyl trichloroacetimidate has given, after removal of protecting groups, 3-O-(β-D-glucopyranosyl)- and 3-O-(β-laminaribiosyl)-isofagomines. Also included are similar glycosylations of a related tetrahydrooxazine. 3-O-(β-D-Glucopyranosyl)- and 3-O-(β-laminaribiosyl)-isofagomines acted as potent inhibitors of a barley 1,3-β-D-glucan endo-hydrolase, with ID₅₀ values of 7.8 and 3.1 μM, respectively.
Keywords: Glycosides; synthesis (org.); enzyme inhibitors; glycosylation; endo-hydrolases
RMID: 0020040206
DOI: 10.1071/CH03227
Appears in Collections:Agriculture, Food and Wine publications

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