Efficient synthesis from D-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-L-arabinitol LABNAc, a potent pyrrolidine inhibitor of hexosaminidases
The synthesis from d-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-l-arabinitol LABNAc proceeded in an overall yield of 25%; the enantiomer, 2-acetamido-1,4-imino-1,2,4-trideoxy-d-arabinitol DABNAc, was prepared from l-lyxonolactone. LABNAc and N-benzyl LABNAc are potent non-competitive inhi...
| Autors principals: | , , , , , , , , |
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| Format: | Journal article |
| Idioma: | English |
| Publicat: |
2007
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| _version_ | 1826280833538850816 |
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| author | Rountree, J Butters, T Wormald, M Dwek, R Asano, N Ikeda, K Evinson, E Nash, R Fleet, G |
| author_facet | Rountree, J Butters, T Wormald, M Dwek, R Asano, N Ikeda, K Evinson, E Nash, R Fleet, G |
| author_sort | Rountree, J |
| collection | OXFORD |
| description | The synthesis from d-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-l-arabinitol LABNAc proceeded in an overall yield of 25%; the enantiomer, 2-acetamido-1,4-imino-1,2,4-trideoxy-d-arabinitol DABNAc, was prepared from l-lyxonolactone. LABNAc and N-benzyl LABNAc are potent non-competitive inhibitors of d-hexosaminidase, whereas N-benzyl DABNAc exhibits weak competitive inhibition of the enzyme; this provides further evidence in support of Asano's hypothesis that while d-imino sugar mimics inhibit d-glycohydrolases competitively, their l-enantiomers show non-competitive inhibition and in the case of iminofuranoses l-enantiomers are usually more potent inhibitors. © 2007 Elsevier Ltd. All rights reserved. |
| first_indexed | 2024-03-07T00:19:40Z |
| format | Journal article |
| id | oxford-uuid:7c1a3131-37bc-486c-9e20-f9ebce014943 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T00:19:40Z |
| publishDate | 2007 |
| record_format | dspace |
| spelling | oxford-uuid:7c1a3131-37bc-486c-9e20-f9ebce0149432022-03-26T20:54:51ZEfficient synthesis from D-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-L-arabinitol LABNAc, a potent pyrrolidine inhibitor of hexosaminidasesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:7c1a3131-37bc-486c-9e20-f9ebce014943EnglishSymplectic Elements at Oxford2007Rountree, JButters, TWormald, MDwek, RAsano, NIkeda, KEvinson, ENash, RFleet, GThe synthesis from d-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-l-arabinitol LABNAc proceeded in an overall yield of 25%; the enantiomer, 2-acetamido-1,4-imino-1,2,4-trideoxy-d-arabinitol DABNAc, was prepared from l-lyxonolactone. LABNAc and N-benzyl LABNAc are potent non-competitive inhibitors of d-hexosaminidase, whereas N-benzyl DABNAc exhibits weak competitive inhibition of the enzyme; this provides further evidence in support of Asano's hypothesis that while d-imino sugar mimics inhibit d-glycohydrolases competitively, their l-enantiomers show non-competitive inhibition and in the case of iminofuranoses l-enantiomers are usually more potent inhibitors. © 2007 Elsevier Ltd. All rights reserved. |
| spellingShingle | Rountree, J Butters, T Wormald, M Dwek, R Asano, N Ikeda, K Evinson, E Nash, R Fleet, G Efficient synthesis from D-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-L-arabinitol LABNAc, a potent pyrrolidine inhibitor of hexosaminidases |
| title | Efficient synthesis from D-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-L-arabinitol LABNAc, a potent pyrrolidine inhibitor of hexosaminidases |
| title_full | Efficient synthesis from D-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-L-arabinitol LABNAc, a potent pyrrolidine inhibitor of hexosaminidases |
| title_fullStr | Efficient synthesis from D-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-L-arabinitol LABNAc, a potent pyrrolidine inhibitor of hexosaminidases |
| title_full_unstemmed | Efficient synthesis from D-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-L-arabinitol LABNAc, a potent pyrrolidine inhibitor of hexosaminidases |
| title_short | Efficient synthesis from D-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-L-arabinitol LABNAc, a potent pyrrolidine inhibitor of hexosaminidases |
| title_sort | efficient synthesis from d lyxonolactone of 2 acetamido 1 4 imino 1 2 4 trideoxy l arabinitol labnac a potent pyrrolidine inhibitor of hexosaminidases |
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