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Probing the Conformational Changes in the Enzymatic Hydrolysis of 2-Acetamido-2-deoxy-β-D-glucopyranosides

✍ Scribed by Matthias Böhm; Andrea Vasella

Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
137 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The isoquinuclidines 7 and 8 were synthesised and tested as inhibitors of hexosaminidases from jack beans and from bovine kidney. These isoquinuclidines mimick the ^1,4^B‐conformer of a N‐acetyl‐glucosamine‐derived β‐d‐glucopyranoside; they are competitive inhibitors with K~i~ values from 0.014 to 0.30 μM. The strong inhibition of these enzymes agrees with the hypothesis that the enzymatic hydrolysis of 2‐acetamido‐2‐deoxy‐β‐d‐glucopyranosides proceeds via a boat‐like conformer with a pseudo‐axial scissile glycosidic bond and a pseudo‐axial acetamido substituent optimally oriented to effect an intramolecular substitution of the aglycon.

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