Matches in SemOpenAlex for { <https://semopenalex.org/work/W2024239114> ?p ?o ?g. }
Showing items 1 to 75 of
75
with 100 items per page.
- W2024239114 endingPage "909" @default.
- W2024239114 startingPage "905" @default.
- W2024239114 abstract "1-Azagalactofagomine [(+)-(3R,4S,5R)-4,5-Dihydroxy-3-(hydroxymethyl)hexahydropyridazine, 2] was synthesised from achiral starting materials in a chemoenzymic synthesis. The racemic Diels–Alder adduct (2-hydroxymethyl-8-methyl-1,6,8-triazabicyclo[4.3.0]non-3-ene-7,9-dione, 5) from addition of pentadienol to 4-methyl-1,2,4-triazoline-3,5-dione was resolved using lipase R-catalysed acetylation. The acetate [(S)-2-acetoxymethyl-8-methyl-1,6,8-triazabicyclo[4.3.0]non-3-ene-7,9-dione, 6] was saponified and treated with MCPBA to give a majority of the syn epoxide [(2R,3S,4R)-3,4-epoxy-2-hydroxymethyl-8-methyl-1,6,8-triazabicyclo[4.3.0]nonane-7,9-dione, 7]. This isomer was subjected to epoxide opening with HI followed by a Woodward reaction-like displacement of the iodide with water and peracetylation to give an all-syn triacetate [(2R,3S,4R)-3,4-diacetoxy-2-acetoxymethyl-1,6,8-triazabicyclo[4.3.0]nonane-7,9-dione, 11]. Finally deacetylation and hydrazinolysis gave 2. The pKa of 2 was determined to be 5.7. 1-Azagalactofagomine was found to be a potent competitive galactosidase inhibitor. The inhibition constants, Ki, were 40, 300 and 7800 nM versus β-galactosidase from Aspergillusoryzae, Eschinchia coli and Saccharomyces fragilis, respectively, and 280 nM vs. α-galactosidase from green coffee beans." @default.
- W2024239114 created "2016-06-24" @default.
- W2024239114 creator A5027669843 @default.
- W2024239114 creator A5073269114 @default.
- W2024239114 date "2001-01-01" @default.
- W2024239114 modified "2023-09-27" @default.
- W2024239114 title "Synthesis of 1-azagalactofagomine, a potent galactosidase inhibitor" @default.
- W2024239114 cites W1990484561 @default.
- W2024239114 cites W2023576692 @default.
- W2024239114 cites W2071958889 @default.
- W2024239114 cites W2076301285 @default.
- W2024239114 cites W2180462291 @default.
- W2024239114 cites W2314340496 @default.
- W2024239114 cites W2950171275 @default.
- W2024239114 cites W2951013852 @default.
- W2024239114 cites W2153613202 @default.
- W2024239114 doi "https://doi.org/10.1039/b007973l" @default.
- W2024239114 hasPublicationYear "2001" @default.
- W2024239114 type Work @default.
- W2024239114 sameAs 2024239114 @default.
- W2024239114 citedByCount "31" @default.
- W2024239114 countsByYear W20242391142012 @default.
- W2024239114 countsByYear W20242391142013 @default.
- W2024239114 countsByYear W20242391142014 @default.
- W2024239114 countsByYear W20242391142015 @default.
- W2024239114 countsByYear W20242391142016 @default.
- W2024239114 countsByYear W20242391142017 @default.
- W2024239114 countsByYear W20242391142019 @default.
- W2024239114 countsByYear W20242391142021 @default.
- W2024239114 countsByYear W20242391142023 @default.
- W2024239114 crossrefType "journal-article" @default.
- W2024239114 hasAuthorship W2024239114A5027669843 @default.
- W2024239114 hasAuthorship W2024239114A5073269114 @default.
- W2024239114 hasConcept C104317684 @default.
- W2024239114 hasConcept C108204754 @default.
- W2024239114 hasConcept C119157956 @default.
- W2024239114 hasConcept C15761196 @default.
- W2024239114 hasConcept C161790260 @default.
- W2024239114 hasConcept C178790620 @default.
- W2024239114 hasConcept C185592680 @default.
- W2024239114 hasConcept C2776920199 @default.
- W2024239114 hasConcept C2780591741 @default.
- W2024239114 hasConcept C55493867 @default.
- W2024239114 hasConcept C71240020 @default.
- W2024239114 hasConceptScore W2024239114C104317684 @default.
- W2024239114 hasConceptScore W2024239114C108204754 @default.
- W2024239114 hasConceptScore W2024239114C119157956 @default.
- W2024239114 hasConceptScore W2024239114C15761196 @default.
- W2024239114 hasConceptScore W2024239114C161790260 @default.
- W2024239114 hasConceptScore W2024239114C178790620 @default.
- W2024239114 hasConceptScore W2024239114C185592680 @default.
- W2024239114 hasConceptScore W2024239114C2776920199 @default.
- W2024239114 hasConceptScore W2024239114C2780591741 @default.
- W2024239114 hasConceptScore W2024239114C55493867 @default.
- W2024239114 hasConceptScore W2024239114C71240020 @default.
- W2024239114 hasIssue "8" @default.
- W2024239114 hasLocation W20242391141 @default.
- W2024239114 hasOpenAccess W2024239114 @default.
- W2024239114 hasPrimaryLocation W20242391141 @default.
- W2024239114 hasRelatedWork W1996022521 @default.
- W2024239114 hasRelatedWork W2002692793 @default.
- W2024239114 hasRelatedWork W2011967164 @default.
- W2024239114 hasRelatedWork W2024239114 @default.
- W2024239114 hasRelatedWork W2049007151 @default.
- W2024239114 hasRelatedWork W2053782898 @default.
- W2024239114 hasRelatedWork W2061631514 @default.
- W2024239114 hasRelatedWork W2397459605 @default.
- W2024239114 hasRelatedWork W2950027484 @default.
- W2024239114 hasRelatedWork W2163930318 @default.
- W2024239114 isParatext "false" @default.
- W2024239114 isRetracted "false" @default.
- W2024239114 magId "2024239114" @default.
- W2024239114 workType "article" @default.