Journal
TETRAHEDRON LETTERS
Volume 53, Issue 33, Pages 4452-4456Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.06.061
Keywords
Processing alpha-glucosidase I; Inversion reaction; 1,2-cis Glucoside; Fluorescence-labeled probe
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Funding
- Ministry of Education, Culture, Sports, Science, and Technology of Japan [21580410]
- ERATO JST
- Mizutani Foundation Research Grant
- Grants-in-Aid for Scientific Research [21580410] Funding Source: KAKEN
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The fluorescence-labeled hexasaccharide (Glc alpha 1-2Glc alpha 1-3Glc alpha 1-3Man alpha 1-2Man alpha 1-2Man alpha) was synthesized as a substrate for the processing enzyme alpha-glucosidase I. To construct the 1,2-cis glucosidic linkages, we employed an alpha stereoselective coupling using the mannosyl donor by assisted neighboring-group participation, followed by conversion of the stereochemistry of the C-2 hydroxyl group in the mannose residue using sequential oxidation of C-2 hydroxyl group to a 2-keto group and stereoselective reduction of the hydroxyl group to the gluco-configuration to provide the corresponding alpha-glucoside derivative. Using this strategy, the three consecutive alpha-glucosidic linkages were easily obtained in a stereoselective manner. Finally, the Dansyl labeled hexasaccharide derivative was used to measure the activity of processing alpha-glucosidase I. (c) 2012 Elsevier Ltd. All rights reserved.
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