An approach to 8 stereoisomers of homonojirimycin from (D)-glucose via kinetic and thermodynamic azido-γ-lactones.
Crystal structures were obtained for the two C2 epimeric azido-γ-lactones 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d-glycero-d-ido-heptono-1,4-lactone and 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d-glycero-d-gulo-heptono-1,4-lactone prepared from kinetic and thermodynamic azide displacements o...
| Main Authors: | , , , , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2013
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| _version_ | 1797092647713636352 |
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| author | Glawar, A Jenkinson, S Newberry, S Thompson, A Nakagawa, S Yoshihara, A Akimitsu, K Izumori, K Butters, T Kato, A Fleet, G |
| author_facet | Glawar, A Jenkinson, S Newberry, S Thompson, A Nakagawa, S Yoshihara, A Akimitsu, K Izumori, K Butters, T Kato, A Fleet, G |
| author_sort | Glawar, A |
| collection | OXFORD |
| description | Crystal structures were obtained for the two C2 epimeric azido-γ-lactones 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d-glycero-d-ido-heptono-1,4-lactone and 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d-glycero-d-gulo-heptono-1,4-lactone prepared from kinetic and thermodynamic azide displacements of a triflate derived from d-glucoheptonolactone. Azido-γ-lactones are very useful intermediates in the synthesis of iminosugars and polyhydroxylated amino acids. In this study two epimeric azido-heptitols allow biotechnological transformations via Izumoring techniques to 8 of the 16 possible homonojirimycin analogues, 5 of which were isolated pure because of the lack of stereoselectivity of the final reductive amination. A side-by-side glycosidase inhibition profile of 11 of the possible 16 HNJ stereoisomers derived from d-glucose and d-mannose is presented. |
| first_indexed | 2024-03-07T03:49:00Z |
| format | Journal article |
| id | oxford-uuid:c08e1e8a-a138-4a92-b84b-f2e135c1f972 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T03:49:00Z |
| publishDate | 2013 |
| record_format | dspace |
| spelling | oxford-uuid:c08e1e8a-a138-4a92-b84b-f2e135c1f9722022-03-27T05:55:18ZAn approach to 8 stereoisomers of homonojirimycin from (D)-glucose via kinetic and thermodynamic azido-γ-lactones.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:c08e1e8a-a138-4a92-b84b-f2e135c1f972EnglishSymplectic Elements at Oxford2013Glawar, AJenkinson, SNewberry, SThompson, ANakagawa, SYoshihara, AAkimitsu, KIzumori, KButters, TKato, AFleet, GCrystal structures were obtained for the two C2 epimeric azido-γ-lactones 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d-glycero-d-ido-heptono-1,4-lactone and 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d-glycero-d-gulo-heptono-1,4-lactone prepared from kinetic and thermodynamic azide displacements of a triflate derived from d-glucoheptonolactone. Azido-γ-lactones are very useful intermediates in the synthesis of iminosugars and polyhydroxylated amino acids. In this study two epimeric azido-heptitols allow biotechnological transformations via Izumoring techniques to 8 of the 16 possible homonojirimycin analogues, 5 of which were isolated pure because of the lack of stereoselectivity of the final reductive amination. A side-by-side glycosidase inhibition profile of 11 of the possible 16 HNJ stereoisomers derived from d-glucose and d-mannose is presented. |
| spellingShingle | Glawar, A Jenkinson, S Newberry, S Thompson, A Nakagawa, S Yoshihara, A Akimitsu, K Izumori, K Butters, T Kato, A Fleet, G An approach to 8 stereoisomers of homonojirimycin from (D)-glucose via kinetic and thermodynamic azido-γ-lactones. |
| title | An approach to 8 stereoisomers of homonojirimycin from (D)-glucose via kinetic and thermodynamic azido-γ-lactones. |
| title_full | An approach to 8 stereoisomers of homonojirimycin from (D)-glucose via kinetic and thermodynamic azido-γ-lactones. |
| title_fullStr | An approach to 8 stereoisomers of homonojirimycin from (D)-glucose via kinetic and thermodynamic azido-γ-lactones. |
| title_full_unstemmed | An approach to 8 stereoisomers of homonojirimycin from (D)-glucose via kinetic and thermodynamic azido-γ-lactones. |
| title_short | An approach to 8 stereoisomers of homonojirimycin from (D)-glucose via kinetic and thermodynamic azido-γ-lactones. |
| title_sort | approach to 8 stereoisomers of homonojirimycin from d glucose via kinetic and thermodynamic azido γ lactones |
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