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Syntheses and Glycosidase Inhibitory Activities of 2-(Aminomethyl)-5-(hydroxymethyl)pyrrolidine-3,4-diol Derivatives

✍ Scribed by Florence Popowycz; Sandrine Gerber-Lemaire; Catherine Schütz; Pierre Vogel

Book ID
102257249
Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
163 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

New 2‐(aminomethyl)‐5‐(hydroxymethyl)pyrrolidine‐3,4‐diol derivatives were synthesized from (5__S__)‐5‐[(trityloxy)methyl]pyrrolidin‐2‐one (6) (Schemes 1 and 2) and their inhibitory activities toward 25 glycosidases assayed (Table). The influence of the configuration of the pyrrolidine ring on glycosidase inhibition was evaluated. (2__R__,3__R__,4__S__,5__R__)‐2‐[(benzylamino)methyl]‐5‐(hydroxymethyl)pyrrolidine‐3,4‐diol ((+)‐21) was found to be a good and selective inhibitor of α‐mannosidase from jack bean (K~i~=1.2 μM) and from almond (K~i~=1.0 μM). Selectivity was lost for the non‐benzylated derivative (2__R__,3__R__,4__S__,5__R__)‐2‐(aminomethyl)‐5‐(hydroxymethyl)pyrrolidine‐3,4‐diol ((+)‐22) which inhibited α‐galactosidases, β‐galactosidases, β‐glucosidases, and α‐N‐acetylgalactosaminidase as well.

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