Analogues of moranoline and MDL 73945. Methyl 6(5)-deoxy-6(5)-(morpholin-4-yl)α-D-glycosides as glucosidase inhibitors

Article abstract of DOI:10.1080/07328300008544083

Methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside (6), or its iodo analogue 7, were subjected to nucleophilic displacement with morpholine to give 8, deacetylation of which gave methyl 6-deoxy-6-(morpholin-4-yl)-α-D-glucopyranoside (3). Similarly, 11, 12 and 21 were prepared. The 6-deoxy-6-iodo derivative 16 was subjected to nucleophilic displacement with morpholine and subsequent acetylation to give 15. Deacetylation of 15 gave 17. The kinetic studies for the inhibition of β-D-glucosidase from sweet almond and using o-nitrophenyl β-D-glucopyranoside as substrate exhibited a K_i value for 21 on the same order as 1-deoxynojirimycin whereas for 3, a K_i value of lesser order was observed.

Full text of DOI:10.1080/07328300008544083

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Analogues of Moranoline and Mdl
73945. Methyl 6(5)-Deoxy-6(5)-
(Morpholin-4-Yl)-α-D-Glycosides as
Glucosidase Inhibitors
El Sayed H. El Ashry , Adel A.-H. Abdel-Rahman , Mohamed
Kattab , Aida H. Shobier & Richard R. Schmidt
a Chemistry Department, Faculty of Science, , Alexandria
University , Alexandria, Egypt
b Chemistry Department, Faculty of Science, , Alexandria
University , Alexandria, Egypt
c Chemistry Department, Faculty of Science, , Alexandria
University , Alexandria, Egypt
d Chemistry Department, Faculty of Science, , Alexandria
University , Alexandria, Egypt
e Fakultät für Chemie, Universität Konstanz , Postfach 5560
M 725, D-78457 Konstanz, Germany
Published online: 27 Feb 2008.
To cite this article: El Sayed H. El Ashry , Adel A.-H. Abdel-Rahman , Mohamed Kattab , Aida
H. Shobier & Richard R. Schmidt (2000) Analogues of Moranoline and Mdl 73945. Methyl 6(5)-
Deoxy-6(5)-(Morpholin-4-Yl)-α-D-Glycosides as Glucosidase Inhibitors, Journal of Carbohydrate
Chemistry, 19:3, 345-357, DOI: 10.1080/07328300008544083
To link to this article: http://dx.doi.org/10.1080/07328300008544083
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