L-DMDP, L-homoDMDP and their C-3 fluorinated derivatives: synthesis and glycosidase-inhibition.
L-DMDP and L-homoDMDP, the enantiomers of naturally occurring DMDP and homoDMDP have been synthesized from D-xylose derived cyclic nitrone 9. Their 3-deoxy-3-fluorinated analogues were also obtained from polyhydroxylated fluorinated cyclic nitrone 10, which was prepared from fluorinated sugar 12 in...
| Huvudupphovsmän: | , , , , , , , , |
|---|---|
| Materialtyp: | Journal article |
| Språk: | English |
| Publicerad: |
2011
|
| _version_ | 1826307202776825856 |
|---|---|
| author | Li, Y Huang, M Yamashita, Y Kato, A Jia, Y Wang, W Fleet, G Nash, R Yu, C |
| author_facet | Li, Y Huang, M Yamashita, Y Kato, A Jia, Y Wang, W Fleet, G Nash, R Yu, C |
| author_sort | Li, Y |
| collection | OXFORD |
| description | L-DMDP and L-homoDMDP, the enantiomers of naturally occurring DMDP and homoDMDP have been synthesized from D-xylose derived cyclic nitrone 9. Their 3-deoxy-3-fluorinated analogues were also obtained from polyhydroxylated fluorinated cyclic nitrone 10, which was prepared from fluorinated sugar 12 in seven steps. Bioactivities of these iminosugars against various glycosidases were evaluated. While L-DMDP and L-homoDMDP are potent inhibitors of α-glucosidases, a sharp decrease of inhibition was found when the C-3 hydroxyl group of these compounds was replaced by fluoride, which showed the great importance of the C-3 hydroxyl in their interaction with enzymes. |
| first_indexed | 2024-03-07T06:59:24Z |
| format | Journal article |
| id | oxford-uuid:ff3797e2-a61f-4a51-b3ae-628788c5c04d |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T06:59:24Z |
| publishDate | 2011 |
| record_format | dspace |
| spelling | oxford-uuid:ff3797e2-a61f-4a51-b3ae-628788c5c04d2022-03-27T13:43:05ZL-DMDP, L-homoDMDP and their C-3 fluorinated derivatives: synthesis and glycosidase-inhibition.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:ff3797e2-a61f-4a51-b3ae-628788c5c04dEnglishSymplectic Elements at Oxford2011Li, YHuang, MYamashita, YKato, AJia, YWang, WFleet, GNash, RYu, CL-DMDP and L-homoDMDP, the enantiomers of naturally occurring DMDP and homoDMDP have been synthesized from D-xylose derived cyclic nitrone 9. Their 3-deoxy-3-fluorinated analogues were also obtained from polyhydroxylated fluorinated cyclic nitrone 10, which was prepared from fluorinated sugar 12 in seven steps. Bioactivities of these iminosugars against various glycosidases were evaluated. While L-DMDP and L-homoDMDP are potent inhibitors of α-glucosidases, a sharp decrease of inhibition was found when the C-3 hydroxyl group of these compounds was replaced by fluoride, which showed the great importance of the C-3 hydroxyl in their interaction with enzymes. |
| spellingShingle | Li, Y Huang, M Yamashita, Y Kato, A Jia, Y Wang, W Fleet, G Nash, R Yu, C L-DMDP, L-homoDMDP and their C-3 fluorinated derivatives: synthesis and glycosidase-inhibition. |
| title | L-DMDP, L-homoDMDP and their C-3 fluorinated derivatives: synthesis and glycosidase-inhibition. |
| title_full | L-DMDP, L-homoDMDP and their C-3 fluorinated derivatives: synthesis and glycosidase-inhibition. |
| title_fullStr | L-DMDP, L-homoDMDP and their C-3 fluorinated derivatives: synthesis and glycosidase-inhibition. |
| title_full_unstemmed | L-DMDP, L-homoDMDP and their C-3 fluorinated derivatives: synthesis and glycosidase-inhibition. |
| title_short | L-DMDP, L-homoDMDP and their C-3 fluorinated derivatives: synthesis and glycosidase-inhibition. |
| title_sort | l dmdp l homodmdp and their c 3 fluorinated derivatives synthesis and glycosidase inhibition |
| work_keys_str_mv | AT liy ldmdplhomodmdpandtheirc3fluorinatedderivativessynthesisandglycosidaseinhibition AT huangm ldmdplhomodmdpandtheirc3fluorinatedderivativessynthesisandglycosidaseinhibition AT yamashitay ldmdplhomodmdpandtheirc3fluorinatedderivativessynthesisandglycosidaseinhibition AT katoa ldmdplhomodmdpandtheirc3fluorinatedderivativessynthesisandglycosidaseinhibition AT jiay ldmdplhomodmdpandtheirc3fluorinatedderivativessynthesisandglycosidaseinhibition AT wangw ldmdplhomodmdpandtheirc3fluorinatedderivativessynthesisandglycosidaseinhibition AT fleetg ldmdplhomodmdpandtheirc3fluorinatedderivativessynthesisandglycosidaseinhibition AT nashr ldmdplhomodmdpandtheirc3fluorinatedderivativessynthesisandglycosidaseinhibition AT yuc ldmdplhomodmdpandtheirc3fluorinatedderivativessynthesisandglycosidaseinhibition |