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|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|
|Citation:||Australian Journal of Chemistry, 2004; 57(3):187-191|
|Publisher:||C S I R O Publishing|
|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|
|Appears in Collections:||Agriculture, Food and Wine publications|
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