Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 19, Issue 1, Pages 58-66Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2010.11.044
Keywords
Synthesis; C-Glycoside; Amino acid; Nucleoside; Galactosyltransferase; Inhibitors
Funding
- Alberta Ingenuity Centre for Carbohydrate Science
- NSERC
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Sugar-amino acid-nucleosides (SAAN) were synthesized to mimic glycosyl nucleotide donors based on the hypothesis that a basic amino acid may interact with carboxylate groups of the enzyme in a manner similar to the diphosphate metal ion complex. C-Glycoside analogues of the D-galactopyranose or L-arabinofuranose ring systems, and four amino acids (lysine, glutamine, tryptophan, and histidine), were chosen for this study. The targets were synthesized and tested against GlfT2, a galactofuranosyltransferase essential for cell wall galactan biosynthesis in Mycobacterium tuberculosis. The inhibition assay showed that analogues containing histidine and tryptophan are moderate inhibitors of GlfT2. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.
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