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Tetrazoles of manno- and rhamno-pyranoses: Contrasting inhibition of mannosidases by [4.3.0] but of rhamnosidase by [3.3.0] bicyclic tetrazoles

Abstract:

The synthesis of tetrazoles derived from D-manno and D- rhamnopyranose from L-gulonolactone and of L-rhamnopyranose from D-gulonolactone is described. These and other materials are assessed as inhibitors of glycosidases. The [4.3.0] tetrazoles of D-manno- and D-rhamnopyranose are inhibitors of human liver α-mannosidase. In contrast the D-furanose analogues show no inhibitory activity whilst the [3.3.0] L-rhamno furanotetrazole is a potent rhamnosidase inhibitor, a potential inhibitor of mycob...

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Publication status:
Published

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Brandstetter, TW More by this author
Hackett, L More by this author
Winchester, BG More by this author
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Publisher:
Elsevier Ltd
Journal:
TETRAHEDRON
Volume:
55
Issue:
14
Pages:
4489-4500
Publication date:
1999-04-02
DOI:
ISSN:
0040-4020
URN:
uuid:aad1171f-ff48-4c6d-9a86-94f590373826
Source identifiers:
36920
Local pid:
pubs:36920
Language:
English

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