The inhibition of N-acetyl-β-d-glucosaminase by the (1→4)- and (1→5)-lactones of N-acetylglucosaminic acid

Abstract

The inhibition of N-acetyl-beta-d-glucosaminase activity by 2-acetamido-2-deoxy-d-gluconolactone was examined. Separation of the (1-->4)- and (1-->5)-lactones was achieved by using paper chromatography or countercurrent distribution and identification was obtained by examination of the relative stability of the components of separated material. Quantitative measurement of the two lactones was by kinetic titration or by a colorimetric method based on their reaction with hydroxylamine. It was shown that only the (1-->5)-lactone acted as an inhibitor of N-acetyl-beta-d-glucosaminase.

Recent Insights into Inhibition, Structure, and Mechanism of Configuration-Retaining Glycosidases

“…A disadvantage of the glycono-1,5-lactones is their tendency to undergo hydrolytic ring opening under mildly basic conditions and conversion into (inactive) 1,4-lactones under mildly acidic conditions, complicating the measurement of inhibition constants, [39,55] and reducing the chances of obtaining crystalline enzyme ± inhibitor complexes for X-ray analysis. [56] This may account for the fact that the transition state character of lactones has remained speculative.…”

Neue Erkenntnisse über Hemmung, Struktur und Mechanismus konfigurationserhaltender Glycosidasen

“…Dieses Verhalten erschwert die Messung von Hemmkonstanten [39,55] und trübt die Aussicht auf die Bildung kristalliner Enzym-Inhibitor-Komplexe für die Röntgenstrukturanalyse. [56] Vermutlich ist das der Grund dafür, daû der Übergangszustandscharakter der Glyconolactone spekulativ blieb.…”

Novel palladium(II)-catalyzed cis-trans isomerization of enol propionates and vinyl halides

“…Chem., 23, 1033(1951. (9) Although rare, preferential labeling has been observed, e.g., coriamyrtin (sesquiterpene): M. Biollaz and D. Arigoni, Chem. Commun., 633 (1969).…”