Synthesis of the naringinase inhibitors L-swainsonine and related 6-C-methyl-L-swainsonine analogues: (6R)-C-methyl-L-swainsonine is a more potent inhibitor of L-rhamnosidase by an order of magnitude than L-swainsonine
Efficient syntheses are reported of the α-l-rhamnosidase inhibitors l-swainsonine [(1R,2S,8S,8aS)-octahydroindolizine-1,2,8-triol], (6R)-C-methyl-l-swainsonine (1R,2S,6R,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol, (6S)-C-methyl-l-swainsonine (1R,2S,6S,8S,8aS)-6-methyloctahydro-indolizine-1,2,8...
| Main Authors: | , , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2008
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| _version_ | 1797099404975407104 |
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| author | Hakansson, A van Ameijde, J Horne, G Nash, R Wormald, M Kato, A Besra, G Gurcha, S Fleet, G |
| author_facet | Hakansson, A van Ameijde, J Horne, G Nash, R Wormald, M Kato, A Besra, G Gurcha, S Fleet, G |
| author_sort | Hakansson, A |
| collection | OXFORD |
| description | Efficient syntheses are reported of the α-l-rhamnosidase inhibitors l-swainsonine [(1R,2S,8S,8aS)-octahydroindolizine-1,2,8-triol], (6R)-C-methyl-l-swainsonine (1R,2S,6R,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol, (6S)-C-methyl-l-swainsonine (1R,2S,6S,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol and related 6-C-methyl hydroxycastanospermines [(1R,2S,6R,7R,8R,8aR)-6-methyl-octahydroindolizine-1,2,6,7,8-pentaol and (1R,2S,6S,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol]. (6R)-C-Methyl-l-swainsonine [Ki = 0.032 μM] is a significantly more potent naringinase inhibitor than l-swainsonine [Ki = 0.45 μM]. © 2007 Elsevier Ltd. All rights reserved. |
| first_indexed | 2024-03-07T05:23:14Z |
| format | Journal article |
| id | oxford-uuid:dfa61298-ac31-44bb-ae3f-b6115322becc |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T05:23:14Z |
| publishDate | 2008 |
| record_format | dspace |
| spelling | oxford-uuid:dfa61298-ac31-44bb-ae3f-b6115322becc2022-03-27T09:40:58ZSynthesis of the naringinase inhibitors L-swainsonine and related 6-C-methyl-L-swainsonine analogues: (6R)-C-methyl-L-swainsonine is a more potent inhibitor of L-rhamnosidase by an order of magnitude than L-swainsonineJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:dfa61298-ac31-44bb-ae3f-b6115322beccEnglishSymplectic Elements at Oxford2008Hakansson, Avan Ameijde, JHorne, GNash, RWormald, MKato, ABesra, GGurcha, SFleet, GEfficient syntheses are reported of the α-l-rhamnosidase inhibitors l-swainsonine [(1R,2S,8S,8aS)-octahydroindolizine-1,2,8-triol], (6R)-C-methyl-l-swainsonine (1R,2S,6R,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol, (6S)-C-methyl-l-swainsonine (1R,2S,6S,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol and related 6-C-methyl hydroxycastanospermines [(1R,2S,6R,7R,8R,8aR)-6-methyl-octahydroindolizine-1,2,6,7,8-pentaol and (1R,2S,6S,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol]. (6R)-C-Methyl-l-swainsonine [Ki = 0.032 μM] is a significantly more potent naringinase inhibitor than l-swainsonine [Ki = 0.45 μM]. © 2007 Elsevier Ltd. All rights reserved. |
| spellingShingle | Hakansson, A van Ameijde, J Horne, G Nash, R Wormald, M Kato, A Besra, G Gurcha, S Fleet, G Synthesis of the naringinase inhibitors L-swainsonine and related 6-C-methyl-L-swainsonine analogues: (6R)-C-methyl-L-swainsonine is a more potent inhibitor of L-rhamnosidase by an order of magnitude than L-swainsonine |
| title | Synthesis of the naringinase inhibitors L-swainsonine and related 6-C-methyl-L-swainsonine analogues: (6R)-C-methyl-L-swainsonine is a more potent inhibitor of L-rhamnosidase by an order of magnitude than L-swainsonine |
| title_full | Synthesis of the naringinase inhibitors L-swainsonine and related 6-C-methyl-L-swainsonine analogues: (6R)-C-methyl-L-swainsonine is a more potent inhibitor of L-rhamnosidase by an order of magnitude than L-swainsonine |
| title_fullStr | Synthesis of the naringinase inhibitors L-swainsonine and related 6-C-methyl-L-swainsonine analogues: (6R)-C-methyl-L-swainsonine is a more potent inhibitor of L-rhamnosidase by an order of magnitude than L-swainsonine |
| title_full_unstemmed | Synthesis of the naringinase inhibitors L-swainsonine and related 6-C-methyl-L-swainsonine analogues: (6R)-C-methyl-L-swainsonine is a more potent inhibitor of L-rhamnosidase by an order of magnitude than L-swainsonine |
| title_short | Synthesis of the naringinase inhibitors L-swainsonine and related 6-C-methyl-L-swainsonine analogues: (6R)-C-methyl-L-swainsonine is a more potent inhibitor of L-rhamnosidase by an order of magnitude than L-swainsonine |
| title_sort | synthesis of the naringinase inhibitors l swainsonine and related 6 c methyl l swainsonine analogues 6r c methyl l swainsonine is a more potent inhibitor of l rhamnosidase by an order of magnitude than l swainsonine |
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