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- W2078640963 abstract "Abstract 1,3-Diamino-1,3-dideoxy- d -threitol ( 1 ) and the corresponding 1,3-diamino-1,3-dideoxy- d -erythritol ( 2 ) were synthesised starting from d -glucose and l -arabinose, respectively. These acyclic diamines inhibited competitively both β- d -glucosidase from sweet almond emulsin and β- d -galactosidase from E. coli with K i -values ranging from 3 to 10 mM. When the suitably blocked diamines were reacted with activated carbonic and thiocarbonic acid derivatives, cyclic urea 5( R )-hydroxy-4( R )-hydroxymethyl-tetrahydropyrimidin-2-one ( 13 ), 5( S )-hydroxy-4( R )-hydroxymethyl-tetrahydropyrimidin-2-one ( 15 ) and thiourea 5( S )-hydroxy-4( R )-hydroxymethyl-tetrahydropyrimidin-2-thione ( 18 ) derivatives were obtained, which conformationally resemble the envelope structure of the d -glucopyranosyl or the d -galactopyranosyl cation. The cyclic carbonamides showed extremely weak competitive inhibition but only with their corresponding enzymes. Compounds 15 and 18 exist, as indicated by 1 H NMR spectroscopy, in an unexpected E -conformation with axial substituents. Upon per- O -acetylation the expected conformation with equatorial substituents is adopted." @default.
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- W2078640963 date "1993-12-01" @default.
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- W2078640963 title "Competitive inhibition of glycoside hydrolases by 1,3-diamino-1,3-dideoxy-tetritols and their cyclic carbonic and thiocarbonic amides" @default.
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- W2078640963 doi "https://doi.org/10.1016/0008-6215(93)84152-v" @default.
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