Matches in SemOpenAlex for { <https://semopenalex.org/work/W1978473899> ?p ?o ?g. }
Showing items 1 to 75 of
75
with 100 items per page.
- W1978473899 abstract "The influence of a substituent at the hydroximo function of the lactam analogue 1 on the inhibition of β- and α-glucosidases is evaluated. In contrast to 1, the O-alkyl oximes 5, 6, 9, and 10 are selective inhibitors of β-glucosidases. Alkylation of the D-gluconohydroximo-1,5-lactam 19 with the triflate 12, or condensation of the thiogluconolactam 20 with the hydroxylamines 14 or 18 afforded the benzylated cellobioside analogues 21 and 23, respectively. The O-alkyl oximes 33 and 39 were prepared similarly (Scheme 3). Deprotection afforded the cellobioside analogues 5 and 6, and the O-alkyl oximes 9 and 10. The lactam O-alkyl oximes 5, 6, 9, and 10 are strong inhibitors of the β-glucosidase from C. saccharolyticum (IC50=0.3 – 8 μM) and, with exception of the dodecyl analogue 9 (IC50=2 μM), moderate-to-weak inhibitors of β-glucosidases from sweet almond (IC50=60 – 1000 μM; see Table). In contrast to the strong inhibition of α-glucosidase from brewer's yeast by 1 (Ki=2.9 μM), the ethers 5, 6, and 10 are weak inhibitors of this enzyme (IC50 between 2500 and >5000 μM). Similarly, the D-galactohydroximo-1,5-lactam 7 is a potent inhibitor of the α-galactosidase from coffee beans and of the β-galactosidases from bovine liver and E. coli (Ki=5, 10, and 0.1 μM, resp.), while the lactoside analogue 8 is a strong inhibitor of the E. coliβ-galactosidase (Ki=0.1 μM), but a moderate-to-weak inhibitor of coffee-bean α-galactosidase and bovine-liver β-galactosidase (Ki=250 μM and IC50=2500 μM, resp.). The galacto-configured lactam oximes 7 and 8 are good inhibitors of the β-glucosidase isolated from C. saccharolyticum (Ki=2.5 and 3.3 μM, resp.)." @default.
- W1978473899 created "2016-06-24" @default.
- W1978473899 creator A5015700327 @default.
- W1978473899 creator A5067409531 @default.
- W1978473899 creator A5075695962 @default.
- W1978473899 date "1998-09-09" @default.
- W1978473899 modified "2023-09-24" @default.
- W1978473899 title "Inhibition of Glycosidases by Lactam Oximes: Influence of the Aglycon in Disaccharide Analogues" @default.
- W1978473899 doi "https://doi.org/10.1002/(sici)1522-2675(19980909)81:9<1710::aid-hlca1710>3.0.co;2-i" @default.
- W1978473899 hasPublicationYear "1998" @default.
- W1978473899 type Work @default.
- W1978473899 sameAs 1978473899 @default.
- W1978473899 citedByCount "24" @default.
- W1978473899 countsByYear W19784738992012 @default.
- W1978473899 countsByYear W19784738992014 @default.
- W1978473899 countsByYear W19784738992018 @default.
- W1978473899 crossrefType "journal-article" @default.
- W1978473899 hasAuthorship W1978473899A5015700327 @default.
- W1978473899 hasAuthorship W1978473899A5067409531 @default.
- W1978473899 hasAuthorship W1978473899A5075695962 @default.
- W1978473899 hasConcept C155647269 @default.
- W1978473899 hasConcept C178790620 @default.
- W1978473899 hasConcept C181199279 @default.
- W1978473899 hasConcept C185592680 @default.
- W1978473899 hasConcept C202751555 @default.
- W1978473899 hasConcept C2776131168 @default.
- W1978473899 hasConcept C2776584326 @default.
- W1978473899 hasConcept C2777346074 @default.
- W1978473899 hasConcept C2777752497 @default.
- W1978473899 hasConcept C2778689049 @default.
- W1978473899 hasConcept C2779648554 @default.
- W1978473899 hasConcept C2780263894 @default.
- W1978473899 hasConcept C55493867 @default.
- W1978473899 hasConcept C71240020 @default.
- W1978473899 hasConceptScore W1978473899C155647269 @default.
- W1978473899 hasConceptScore W1978473899C178790620 @default.
- W1978473899 hasConceptScore W1978473899C181199279 @default.
- W1978473899 hasConceptScore W1978473899C185592680 @default.
- W1978473899 hasConceptScore W1978473899C202751555 @default.
- W1978473899 hasConceptScore W1978473899C2776131168 @default.
- W1978473899 hasConceptScore W1978473899C2776584326 @default.
- W1978473899 hasConceptScore W1978473899C2777346074 @default.
- W1978473899 hasConceptScore W1978473899C2777752497 @default.
- W1978473899 hasConceptScore W1978473899C2778689049 @default.
- W1978473899 hasConceptScore W1978473899C2779648554 @default.
- W1978473899 hasConceptScore W1978473899C2780263894 @default.
- W1978473899 hasConceptScore W1978473899C55493867 @default.
- W1978473899 hasConceptScore W1978473899C71240020 @default.
- W1978473899 hasLocation W19784738991 @default.
- W1978473899 hasOpenAccess W1978473899 @default.
- W1978473899 hasPrimaryLocation W19784738991 @default.
- W1978473899 hasRelatedWork W1971172322 @default.
- W1978473899 hasRelatedWork W1973569843 @default.
- W1978473899 hasRelatedWork W1979710240 @default.
- W1978473899 hasRelatedWork W1995911981 @default.
- W1978473899 hasRelatedWork W2001011969 @default.
- W1978473899 hasRelatedWork W2011230730 @default.
- W1978473899 hasRelatedWork W2028231006 @default.
- W1978473899 hasRelatedWork W2050362679 @default.
- W1978473899 hasRelatedWork W2062188771 @default.
- W1978473899 hasRelatedWork W2077813646 @default.
- W1978473899 hasRelatedWork W2080264145 @default.
- W1978473899 hasRelatedWork W2087261515 @default.
- W1978473899 hasRelatedWork W2111725279 @default.
- W1978473899 hasRelatedWork W2124510570 @default.
- W1978473899 hasRelatedWork W2139013924 @default.
- W1978473899 hasRelatedWork W2149632578 @default.
- W1978473899 hasRelatedWork W2949755232 @default.
- W1978473899 hasRelatedWork W2951034201 @default.
- W1978473899 hasRelatedWork W2951341620 @default.
- W1978473899 hasRelatedWork W2153613202 @default.
- W1978473899 isParatext "false" @default.
- W1978473899 isRetracted "false" @default.
- W1978473899 magId "1978473899" @default.
- W1978473899 workType "article" @default.