Tetrazoles of manno- and rhamno-pyranoses: Contrasting inhibition of mannosidases by [4.3.0] but of rhamnosidase by [3.3.0] bicyclic tetrazoles
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...
| Main Authors: | , , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
Elsevier
1999
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| _version_ | 1797087895128899584 |
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| author | Davis, B Brandstetter, T Hackett, L Winchester, BG Nash, R Watson, A Griffiths, R Smith, C Fleet, G |
| author_facet | Davis, B Brandstetter, T Hackett, L Winchester, BG Nash, R Watson, A Griffiths, R Smith, C Fleet, G |
| author_sort | Davis, B |
| collection | OXFORD |
| description | 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 mycobacterial cell wall biosynthesis and as such may provide a strategy for the treatment of tuberculosis. |
| first_indexed | 2024-03-07T02:42:08Z |
| format | Journal article |
| id | oxford-uuid:aad1171f-ff48-4c6d-9a86-94f590373826 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T02:42:08Z |
| publishDate | 1999 |
| publisher | Elsevier |
| record_format | dspace |
| spelling | oxford-uuid:aad1171f-ff48-4c6d-9a86-94f5903738262022-03-27T03:17:37ZTetrazoles of manno- and rhamno-pyranoses: Contrasting inhibition of mannosidases by [4.3.0] but of rhamnosidase by [3.3.0] bicyclic tetrazolesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:aad1171f-ff48-4c6d-9a86-94f590373826EnglishSymplectic Elements at OxfordElsevier1999Davis, BBrandstetter, THackett, LWinchester, BGNash, RWatson, AGriffiths, RSmith, CFleet, GThe 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 mycobacterial cell wall biosynthesis and as such may provide a strategy for the treatment of tuberculosis. |
| spellingShingle | Davis, B Brandstetter, T Hackett, L Winchester, BG Nash, R Watson, A Griffiths, R Smith, C Fleet, G Tetrazoles of manno- and rhamno-pyranoses: Contrasting inhibition of mannosidases by [4.3.0] but of rhamnosidase by [3.3.0] bicyclic tetrazoles |
| title | Tetrazoles of manno- and rhamno-pyranoses: Contrasting inhibition of mannosidases by [4.3.0] but of rhamnosidase by [3.3.0] bicyclic tetrazoles |
| title_full | Tetrazoles of manno- and rhamno-pyranoses: Contrasting inhibition of mannosidases by [4.3.0] but of rhamnosidase by [3.3.0] bicyclic tetrazoles |
| title_fullStr | Tetrazoles of manno- and rhamno-pyranoses: Contrasting inhibition of mannosidases by [4.3.0] but of rhamnosidase by [3.3.0] bicyclic tetrazoles |
| title_full_unstemmed | Tetrazoles of manno- and rhamno-pyranoses: Contrasting inhibition of mannosidases by [4.3.0] but of rhamnosidase by [3.3.0] bicyclic tetrazoles |
| title_short | Tetrazoles of manno- and rhamno-pyranoses: Contrasting inhibition of mannosidases by [4.3.0] but of rhamnosidase by [3.3.0] bicyclic tetrazoles |
| title_sort | tetrazoles of manno and rhamno pyranoses contrasting inhibition of mannosidases by 4 3 0 but of rhamnosidase by 3 3 0 bicyclic tetrazoles |
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