L-Idoseptanosides: substratesd D-glucosidases?

Based on the reported glycosidase inhibitory activities of 1,6-dideoxy-1,6-imino-L-iditol, the corresponding aryl glycosides 4-nitrophenyl alpha- and beta-L -idoseptano side 7 and 8 were synthesised as possible glycosidase substrates. Despite their inherently larger size, these septanosides were ind...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 17; no. 2; pp. 234 - 239
Main Authors Tauss, A, Steiner, AJ, Stutz, AE, Tarling, CA, Withers, SG, Wrodnigg, TM
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 23.01.2006
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
MECHANISM
INTERMEDIATE
GLYCOSIDASE INHIBITORS
GALACTOSIDASE
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Summary:Based on the reported glycosidase inhibitory activities of 1,6-dideoxy-1,6-imino-L-iditol, the corresponding aryl glycosides 4-nitrophenyl alpha- and beta-L -idoseptano side 7 and 8 were synthesised as possible glycosidase substrates. Despite their inherently larger size, these septanosides were indeed shown to be glycosidase substrates, albeit weak ones. In addition, these two substrate analogues 7 and 8 also demonstrated a remarkable degree of selectivity for beta- and alpha-glucosidases, respectively. (c) 2005 Elsevier Ltd. All rights reserved.
ISSN:0957-4166
DOI:10.1016/j.tetasy.2005.12.007