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Synthesis of iminoalditol analogues of galactofuranosides and their activities against glycosidases

From National Research Council Canada

DOIResolve DOI: https://doi.org/10.1016/j.carres.2008.07.013
AuthorSearch for: 1; Search for: 1; Search for: 1; Search for: 1; Search for: ; Search for: 1
Affiliation
  1. National Research Council of Canada. NRC Institute for Biological Sciences
FormatText, Article
SubjectAmination; Canada; INHIBITOR; Liver; Mixture; Synthesis; Synthesis
Abstract
Iminoalditol analogues of galactofuranosides were synthesized from 1-C-(2'-oxo-propyl)-1,4-dideoxy-1,4-imino-d-galactosides and different amines by reductive amination, followed by removal of protecting groups. The activity of these compounds against galactosidases and other glycosidases was investigated. The best inhibitor against beta-galactosidase (bovine liver) is a diastereomeric mixture of an iminoalditol (10h), which contains a hydrophobic hexadecyl aglycon (R=C(16)H(33)), whereas no significant inhibitory activity was observed with compounds having a hydrophilic aglycon. Surprisingly, activation of alpha-galactosidase (coffee bean) by 10h was also observed. Because these results were obtained from a mixture of iminoalditols, the inhibition and activation of glycosidases could result from different diastereomers
Publication date
In
  • Acoustics, Speech, and Signal Processing Newsletter, IEEE 343, no. 17 (2008): 2878–2886.
LanguageEnglish
NRC numberSANDBHOR2008A
SANDBHOR2008
NPARC number9370349
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Record identifier63e275e8-d034-453c-9dc7-c3cfc20539a8
Record created2009-07-10
Record modified2020-04-15
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