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  4. Synthesis of N-substituted (3S,4S)- and (3R,4R)-pyrrolidine-3,4-diols: Search for new glycosidase inhibitors
 
research article

Synthesis of N-substituted (3S,4S)- and (3R,4R)-pyrrolidine-3,4-diols: Search for new glycosidase inhibitors

Lysek, R.  
•
Vogel, P.  
2004
Helvetica Chimica Acta

N-Substituted (3S,4S)- and (3R,4R)-pyrrolidine-3,4-diols 9 and 10, respectively, were derived from (+)-L- and (-)-D-tartaric acid, respectively. Compounds 9k, 91, and 9m with the N-substituents, BnNH(CH2)(2), 4-Phc(6)H(4)CH(2)NH(CH2)(2) and 4-ClC6H4CH2NH(CH2)(2), respectively, showed modest inhibitory activities toward aD-amyloglucosidases from Aspergillus niger and from Rhizopus mold (Table 1). Unexpectedly, several (3R,4R)-pyrrolidine-3,4-diols 10 showed inhibitory activities toward alpha-D-mannosidases from almonds and from jack bean (Table 3). N-Substitution by the NH2(CH2)(2) group, i.e., 10g, led to the highest potency.

  • Details
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Type
research article
DOI
10.1002/hlca.200490282
Web of Science ID

WOS:000226108200014

Author(s)
Lysek, R.  
Vogel, P.  
Date Issued

2004

Published in
Helvetica Chimica Acta
Volume

87

Issue

12

Start page

3167

End page

3181

Subjects

Immunodeficiency-virus type-1

•

hyacinthoides-non-scripta

•

hiv entry

•

inhibitors

•

tartaric acid

•

asymmetric hydrogenation

•

envelope

•

glycoprotein

•

glucosidase inhibitor

•

morus-alba

•

derivatives

•

alkaloids

Note

Ecole Polytech Fed Lausanne, Lab Glyochim & Synth Asymetr, BCH, CH-1015 Lausanne, Switzerland.

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/20.500.14299/219829
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