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Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors
N-Alkylation at the ring nitrogen of the D-galactosidase inhibitor 1-deoxygalactonojirimycin with a functionalised C(6) alkyl chain followed by modification with different aromatic substituents provided lipophilic 1-deoxygalactonojirimycin derivatives which exhibit inhibitory properties against β-gl...
| Autores principales: | , , , , , , , , , , , , , |
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| Formato: | Texto |
| Lenguaje: | English |
| Publicado: |
Beilstein-Institut
2010
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2874416/ https://www.ncbi.nlm.nih.gov/pubmed/20502610 http://dx.doi.org/10.3762/bjoc.6.21 |
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| author | Schitter, Georg Scheucher, Elisabeth Steiner, Andreas J Stütz, Arnold E Thonhofer, Martin Tarling, Chris A Withers, Stephen G Wicki, Jacqueline Fantur, Katrin Paschke, Eduard Mahuran, Don J Rigat, Brigitte A Tropak, Michael Wrodnigg, Tanja M |
| author_facet | Schitter, Georg Scheucher, Elisabeth Steiner, Andreas J Stütz, Arnold E Thonhofer, Martin Tarling, Chris A Withers, Stephen G Wicki, Jacqueline Fantur, Katrin Paschke, Eduard Mahuran, Don J Rigat, Brigitte A Tropak, Michael Wrodnigg, Tanja M |
| author_sort | Schitter, Georg |
| collection | PubMed |
| description | N-Alkylation at the ring nitrogen of the D-galactosidase inhibitor 1-deoxygalactonojirimycin with a functionalised C(6) alkyl chain followed by modification with different aromatic substituents provided lipophilic 1-deoxygalactonojirimycin derivatives which exhibit inhibitory properties against β-glycosidases from E. coli and Agrobacterium sp. as well as green coffee bean α-galactosidase. In preliminary studies, these compounds also showed potential as chemical chaperones for GM1-gangliosidosis related β-galactosidase mutants. |
| format | Text |
| id | pubmed-2874416 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2010 |
| publisher | Beilstein-Institut |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-28744162010-05-25 Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors Schitter, Georg Scheucher, Elisabeth Steiner, Andreas J Stütz, Arnold E Thonhofer, Martin Tarling, Chris A Withers, Stephen G Wicki, Jacqueline Fantur, Katrin Paschke, Eduard Mahuran, Don J Rigat, Brigitte A Tropak, Michael Wrodnigg, Tanja M Beilstein J Org Chem Full Research Paper N-Alkylation at the ring nitrogen of the D-galactosidase inhibitor 1-deoxygalactonojirimycin with a functionalised C(6) alkyl chain followed by modification with different aromatic substituents provided lipophilic 1-deoxygalactonojirimycin derivatives which exhibit inhibitory properties against β-glycosidases from E. coli and Agrobacterium sp. as well as green coffee bean α-galactosidase. In preliminary studies, these compounds also showed potential as chemical chaperones for GM1-gangliosidosis related β-galactosidase mutants. Beilstein-Institut 2010-03-01 /pmc/articles/PMC2874416/ /pubmed/20502610 http://dx.doi.org/10.3762/bjoc.6.21 Text en Copyright © 2010, Schitter et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
| spellingShingle | Full Research Paper Schitter, Georg Scheucher, Elisabeth Steiner, Andreas J Stütz, Arnold E Thonhofer, Martin Tarling, Chris A Withers, Stephen G Wicki, Jacqueline Fantur, Katrin Paschke, Eduard Mahuran, Don J Rigat, Brigitte A Tropak, Michael Wrodnigg, Tanja M Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors |
| title | Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors |
| title_full | Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors |
| title_fullStr | Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors |
| title_full_unstemmed | Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors |
| title_short | Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors |
| title_sort | synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as d-galactosidase inhibitors |
| topic | Full Research Paper |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2874416/ https://www.ncbi.nlm.nih.gov/pubmed/20502610 http://dx.doi.org/10.3762/bjoc.6.21 |
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