Nine of 16 stereoisomeric polyhydroxylated proline amides are potent β-N-acetylhexosaminidase inhibitors.
All 16 stereoisomeric N-methyl 5-(hydroxymethyl)-3,4-dihydroxyproline amides have been synthesized from lactones accessible from the enantiomers of glucuronolactone. Nine stereoisomers, including all eight with a (3R)-hydroxyl configuration, are low to submicromolar inhibitors of β-N-acetylhexosamin...
| Asıl Yazarlar: | , , , , , , , , , , , , , |
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| Materyal Türü: | Journal article |
| Dil: | English |
| Baskı/Yayın Bilgisi: |
2014
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| _version_ | 1826270892374622208 |
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| author | Ayers, B Glawar, A Martínez, R Ngo, N Liu, Z Fleet, G Butters, T Nash, R Yu, C Wormald, M Nakagawa, S Adachi, I Kato, A Jenkinson, S |
| author_facet | Ayers, B Glawar, A Martínez, R Ngo, N Liu, Z Fleet, G Butters, T Nash, R Yu, C Wormald, M Nakagawa, S Adachi, I Kato, A Jenkinson, S |
| author_sort | Ayers, B |
| collection | OXFORD |
| description | All 16 stereoisomeric N-methyl 5-(hydroxymethyl)-3,4-dihydroxyproline amides have been synthesized from lactones accessible from the enantiomers of glucuronolactone. Nine stereoisomers, including all eight with a (3R)-hydroxyl configuration, are low to submicromolar inhibitors of β-N-acetylhexosaminidases. A structural correlation between the proline amides is found with the ADMDP-acetamide analogues bearing an acetamidomethylpyrrolidine motif. The proline amides are generally more potent than their ADMDP-acetamide equivalents. β-N-Acetylhexosaminidase inhibition by an azetidine ADMDP-acetamide analogue is compared to an azetidine carboxylic acid amide. None of the amides are good α-N-acetylgalactosaminidase inhibitors. |
| first_indexed | 2024-03-06T21:47:59Z |
| format | Journal article |
| id | oxford-uuid:4a44e97e-6b70-4341-8af9-a253b9d9470d |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T21:47:59Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | oxford-uuid:4a44e97e-6b70-4341-8af9-a253b9d9470d2022-03-26T15:36:31ZNine of 16 stereoisomeric polyhydroxylated proline amides are potent β-N-acetylhexosaminidase inhibitors.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:4a44e97e-6b70-4341-8af9-a253b9d9470dEnglishSymplectic Elements at Oxford2014Ayers, BGlawar, AMartínez, RNgo, NLiu, ZFleet, GButters, TNash, RYu, CWormald, MNakagawa, SAdachi, IKato, AJenkinson, SAll 16 stereoisomeric N-methyl 5-(hydroxymethyl)-3,4-dihydroxyproline amides have been synthesized from lactones accessible from the enantiomers of glucuronolactone. Nine stereoisomers, including all eight with a (3R)-hydroxyl configuration, are low to submicromolar inhibitors of β-N-acetylhexosaminidases. A structural correlation between the proline amides is found with the ADMDP-acetamide analogues bearing an acetamidomethylpyrrolidine motif. The proline amides are generally more potent than their ADMDP-acetamide equivalents. β-N-Acetylhexosaminidase inhibition by an azetidine ADMDP-acetamide analogue is compared to an azetidine carboxylic acid amide. None of the amides are good α-N-acetylgalactosaminidase inhibitors. |
| spellingShingle | Ayers, B Glawar, A Martínez, R Ngo, N Liu, Z Fleet, G Butters, T Nash, R Yu, C Wormald, M Nakagawa, S Adachi, I Kato, A Jenkinson, S Nine of 16 stereoisomeric polyhydroxylated proline amides are potent β-N-acetylhexosaminidase inhibitors. |
| title | Nine of 16 stereoisomeric polyhydroxylated proline amides are potent β-N-acetylhexosaminidase inhibitors. |
| title_full | Nine of 16 stereoisomeric polyhydroxylated proline amides are potent β-N-acetylhexosaminidase inhibitors. |
| title_fullStr | Nine of 16 stereoisomeric polyhydroxylated proline amides are potent β-N-acetylhexosaminidase inhibitors. |
| title_full_unstemmed | Nine of 16 stereoisomeric polyhydroxylated proline amides are potent β-N-acetylhexosaminidase inhibitors. |
| title_short | Nine of 16 stereoisomeric polyhydroxylated proline amides are potent β-N-acetylhexosaminidase inhibitors. |
| title_sort | nine of 16 stereoisomeric polyhydroxylated proline amides are potent β n acetylhexosaminidase inhibitors |
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