C-branched iminosugars: α-glucosidase inhibition by enantiomers of isoDMDP, isoDGDP, and isoDAB-L-isoDMDP compared to miglitol and miglustat.
The Ho crossed aldol condensation provides access to a series of carbon branched iminosugars as exemplified by the synthesis of enantiomeric pairs of isoDMDP, isoDGDP, and isoDAB, allowing comparison of their biological activities with three linear isomeric natural products DMDP, DGDP, and DAB and t...
| Main Authors: | , , , , , , , , , , , , , , , |
|---|---|
| Format: | Journal article |
| Language: | English |
| Published: |
2013
|
| _version_ | 1797098577576591360 |
|---|---|
| author | Jenkinson, S Best, D Saville, A Mui, J Martínez, R Nakagawa, S Kunimatsu, T Alonzi, D Butters, T Norez, C Becq, F Blériot, Y Wilson, F Weymouth-Wilson, A Kato, A Fleet, G |
| author_facet | Jenkinson, S Best, D Saville, A Mui, J Martínez, R Nakagawa, S Kunimatsu, T Alonzi, D Butters, T Norez, C Becq, F Blériot, Y Wilson, F Weymouth-Wilson, A Kato, A Fleet, G |
| author_sort | Jenkinson, S |
| collection | OXFORD |
| description | The Ho crossed aldol condensation provides access to a series of carbon branched iminosugars as exemplified by the synthesis of enantiomeric pairs of isoDMDP, isoDGDP, and isoDAB, allowing comparison of their biological activities with three linear isomeric natural products DMDP, DGDP, and DAB and their enantiomers. L-IsoDMDP [(2S,3S,4R)-2,4-bis(hydroxymethyl)pyrrolidine-3,4-diol], prepared in 11 steps in an overall yield of 45% from d-lyxonolactone, is a potent specific competitive inhibitor of gut disaccharidases [K(i) 0.081 μM for rat intestinal maltase] and is more effective in the suppression of hyperglycaemia in a maltose loading test than miglitol, a drug presently used in the treatment of late onset diabetes. The partial rescue of the defective F508del-CFTR function in CF-KM4 cells by L-isoDMDP is compared with miglustat and isoLAB in an approach to the treatment of cystic fibrosis. |
| first_indexed | 2024-03-07T05:11:36Z |
| format | Journal article |
| id | oxford-uuid:dbbe2635-7179-45ae-95d2-00bc59d0c97a |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T05:11:36Z |
| publishDate | 2013 |
| record_format | dspace |
| spelling | oxford-uuid:dbbe2635-7179-45ae-95d2-00bc59d0c97a2022-03-27T09:12:42ZC-branched iminosugars: α-glucosidase inhibition by enantiomers of isoDMDP, isoDGDP, and isoDAB-L-isoDMDP compared to miglitol and miglustat.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:dbbe2635-7179-45ae-95d2-00bc59d0c97aEnglishSymplectic Elements at Oxford2013Jenkinson, SBest, DSaville, AMui, JMartínez, RNakagawa, SKunimatsu, TAlonzi, DButters, TNorez, CBecq, FBlériot, YWilson, FWeymouth-Wilson, AKato, AFleet, GThe Ho crossed aldol condensation provides access to a series of carbon branched iminosugars as exemplified by the synthesis of enantiomeric pairs of isoDMDP, isoDGDP, and isoDAB, allowing comparison of their biological activities with three linear isomeric natural products DMDP, DGDP, and DAB and their enantiomers. L-IsoDMDP [(2S,3S,4R)-2,4-bis(hydroxymethyl)pyrrolidine-3,4-diol], prepared in 11 steps in an overall yield of 45% from d-lyxonolactone, is a potent specific competitive inhibitor of gut disaccharidases [K(i) 0.081 μM for rat intestinal maltase] and is more effective in the suppression of hyperglycaemia in a maltose loading test than miglitol, a drug presently used in the treatment of late onset diabetes. The partial rescue of the defective F508del-CFTR function in CF-KM4 cells by L-isoDMDP is compared with miglustat and isoLAB in an approach to the treatment of cystic fibrosis. |
| spellingShingle | Jenkinson, S Best, D Saville, A Mui, J Martínez, R Nakagawa, S Kunimatsu, T Alonzi, D Butters, T Norez, C Becq, F Blériot, Y Wilson, F Weymouth-Wilson, A Kato, A Fleet, G C-branched iminosugars: α-glucosidase inhibition by enantiomers of isoDMDP, isoDGDP, and isoDAB-L-isoDMDP compared to miglitol and miglustat. |
| title | C-branched iminosugars: α-glucosidase inhibition by enantiomers of isoDMDP, isoDGDP, and isoDAB-L-isoDMDP compared to miglitol and miglustat. |
| title_full | C-branched iminosugars: α-glucosidase inhibition by enantiomers of isoDMDP, isoDGDP, and isoDAB-L-isoDMDP compared to miglitol and miglustat. |
| title_fullStr | C-branched iminosugars: α-glucosidase inhibition by enantiomers of isoDMDP, isoDGDP, and isoDAB-L-isoDMDP compared to miglitol and miglustat. |
| title_full_unstemmed | C-branched iminosugars: α-glucosidase inhibition by enantiomers of isoDMDP, isoDGDP, and isoDAB-L-isoDMDP compared to miglitol and miglustat. |
| title_short | C-branched iminosugars: α-glucosidase inhibition by enantiomers of isoDMDP, isoDGDP, and isoDAB-L-isoDMDP compared to miglitol and miglustat. |
| title_sort | c branched iminosugars α glucosidase inhibition by enantiomers of isodmdp isodgdp and isodab l isodmdp compared to miglitol and miglustat |
| work_keys_str_mv | AT jenkinsons cbranchediminosugarsaglucosidaseinhibitionbyenantiomersofisodmdpisodgdpandisodablisodmdpcomparedtomiglitolandmiglustat AT bestd cbranchediminosugarsaglucosidaseinhibitionbyenantiomersofisodmdpisodgdpandisodablisodmdpcomparedtomiglitolandmiglustat AT savillea cbranchediminosugarsaglucosidaseinhibitionbyenantiomersofisodmdpisodgdpandisodablisodmdpcomparedtomiglitolandmiglustat AT muij cbranchediminosugarsaglucosidaseinhibitionbyenantiomersofisodmdpisodgdpandisodablisodmdpcomparedtomiglitolandmiglustat AT martinezr cbranchediminosugarsaglucosidaseinhibitionbyenantiomersofisodmdpisodgdpandisodablisodmdpcomparedtomiglitolandmiglustat AT nakagawas cbranchediminosugarsaglucosidaseinhibitionbyenantiomersofisodmdpisodgdpandisodablisodmdpcomparedtomiglitolandmiglustat AT kunimatsut cbranchediminosugarsaglucosidaseinhibitionbyenantiomersofisodmdpisodgdpandisodablisodmdpcomparedtomiglitolandmiglustat AT alonzid cbranchediminosugarsaglucosidaseinhibitionbyenantiomersofisodmdpisodgdpandisodablisodmdpcomparedtomiglitolandmiglustat AT butterst cbranchediminosugarsaglucosidaseinhibitionbyenantiomersofisodmdpisodgdpandisodablisodmdpcomparedtomiglitolandmiglustat AT norezc cbranchediminosugarsaglucosidaseinhibitionbyenantiomersofisodmdpisodgdpandisodablisodmdpcomparedtomiglitolandmiglustat AT becqf cbranchediminosugarsaglucosidaseinhibitionbyenantiomersofisodmdpisodgdpandisodablisodmdpcomparedtomiglitolandmiglustat AT blerioty cbranchediminosugarsaglucosidaseinhibitionbyenantiomersofisodmdpisodgdpandisodablisodmdpcomparedtomiglitolandmiglustat AT wilsonf cbranchediminosugarsaglucosidaseinhibitionbyenantiomersofisodmdpisodgdpandisodablisodmdpcomparedtomiglitolandmiglustat AT weymouthwilsona cbranchediminosugarsaglucosidaseinhibitionbyenantiomersofisodmdpisodgdpandisodablisodmdpcomparedtomiglitolandmiglustat AT katoa cbranchediminosugarsaglucosidaseinhibitionbyenantiomersofisodmdpisodgdpandisodablisodmdpcomparedtomiglitolandmiglustat AT fleetg cbranchediminosugarsaglucosidaseinhibitionbyenantiomersofisodmdpisodgdpandisodablisodmdpcomparedtomiglitolandmiglustat |