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  4. Synthesis and glycosidase inhibitory activities of 2-(aminoalkyl)pyrrolidine-3,4-diol derivatives
 
research article

Synthesis and glycosidase inhibitory activities of 2-(aminoalkyl)pyrrolidine-3,4-diol derivatives

Carmona, AT  
•
Popowycz, F  
•
Gerber-Lemaire, S  
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2003
Bioorganic & Medicinal Chemistry

Several 2-(aminomethyl)-and 2-(2-aminoethyl)-pyrrolidine-3,4-diol derivatives have been assayed for their inhibitory activities towards glycosidases. Good inhibitors of alpha-mannosidases must have the (2R,3R,4S) configuration and possess 2-(benzylamino)methyl substituents. Stereomers with the (2S,3R,4S) configuration are also competitive inhibitors of alpha-mannosidases, but less potent as they share the configuration of C(1), C(2), C(3) Of beta-D-mannosides rather than that Of alpha-D-mannosides. Interestingly, (2S,3R,4S)-2-{2-[(4-phenyl)phenylamino]ethyl}pyrrolidine-3,4-diol (12g) inhibits several enzymes, for instance alpha-L-fucosidase from bovine epididymis (K-i = 6.5 muM, competitive), alpha-galactosidase from bovine liver (K-i = 5 muM, mixed) and alpha-mannosidase from jack bean (K-i = 102 muM, mixed). Diamines such as (2R,3S,4R)-2-[2-(phenylamino) or 2-(benzylamino)ethyl]pyrrolidine-3,4-diol (ent-1 2a, ent-12b) inhibit P-glucosidase from almonds (K-i = 13-40 muM, competitive). (C) 2003 Elsevier Ltd. All rights reserved.

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Type
research article
DOI
10.1016/j.bmc.2003.09.020
Web of Science ID

WOS:000186614400005

Author(s)
Carmona, AT  
Popowycz, F  
Gerber-Lemaire, S  
Rodriguez-Garcia, E  
Schutz, C  
Vogel, P  
Robina, I
Date Issued

2003

Published in
Bioorganic & Medicinal Chemistry
Volume

11

Issue

23

Start page

4897

End page

4911

Subjects

aza-c-disaccharides

•

biological evaluation

•

asymmetric-synthesis

•

sugarmimics

•

castanospermine

•

mannosidase

•

swainsonine

•

discovery

•

2

•

5-dideoxy-2

•

5-imino-d-mannitol

•

iminodisaccharides

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LGSA  
Available on Infoscience
November 9, 2005
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/219451
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