Synthesis of iminoalditol analogues of galactofuranosides and their activities against glycosidases
Resource
Carbohydrate Research, 343(17), 2878-2886
Journal
Carbohydrate Research
Pages
2878-2886
Date Issued
2008
Date
2008
Author(s)
Sandbhor, Mahendra
Bhasin, Milan
Williams, Dean T.
Hsieh, Margaret
Wu, Shih-Hsiung
Zou, Wei
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.
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