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https://hdl.handle.net/2440/75
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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: an international journal for chemical science, 2004; 57(3):187-191 |
Publisher: | C S I R O Publishing |
Issue Date: | 2004 |
ISSN: | 0004-9425 1445-0038 |
Statement of Responsibility: | 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 |
DOI: | 10.1071/CH03227 |
Published version: | http://dx.doi.org/10.1071/ch03227 |
Appears in Collections: | Agriculture, Food and Wine publications Aurora harvest 6 |
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