Publication

Syntheses and glycosidase inhibitory activities of 2-(aminomethyl)-5(hydroxymethyl)pyrrolidine-3,4-diol derivatives

Pierre Vogel
2004
Journal Articles

Abstract

New 2-(aminomethyl)-5-(hydroxymethyl)pyrrolidine-3,4-diol derivatives were synthesized from (5S)-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. (2R,3R,4S,5R)-2-[(benzylamino)methyl]-5-(hydroxymethyl)pyrrolidine-3,4-d iol ((+)-21) was found to be a good and selective inhibitor of a-mannosidase from jack bean (K-i=1.2 muM) and from almond (K-i= 1.0 muM). Selectivity was lost for the non-benzylated derivative (2R,3R,4S,5R)-2-(aminomethyl)-5-(hydroxymethyl)pyrrolidine-3,4-diol ((+)-22) which inhibited alpha-galactosidases, beta-galactosidases, beta-glucosidases, and alpha-N-acetylgalactosaminidase as well.

Official source

https://infoscience.epfl.ch/entities/publication/b8ba596d-78ca-4777-80c6-97ad9338ade7

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Pierre Vogel
2004
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/b8ba596d-78ca-4777-80c6-97ad9338ade7

About this result

Related concepts (26)

Scheme (mathematics)

In mathematics, a scheme is a mathematical structure that enlarges the notion of algebraic variety in several ways, such as taking account of multiplicities (the equations x = 0 and x2 = 0 define the same algebraic variety but different schemes) and allowing "varieties" defined over any commutative ring (for example, Fermat curves are defined over the integers). Scheme theory was introduced by Alexander Grothendieck in 1960 in his treatise "Éléments de géométrie algébrique"; one of its aims was developing the formalism needed to solve deep problems of algebraic geometry, such as the Weil conjectures (the last of which was proved by Pierre Deligne).

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Related publications (2)

Syntheses and glycosidase inhibitory activities of 2-(aminomethyl)-5(hydroxymethyl)pyrrolidine-3,4-diol derivatives

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