Synthesis of sugar-amino acid-nucleosides as potential glycosyltransferase inhibitors |
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Authors: | Vembaiyan Kannan Pearcey Jean A Bhasin Milan Lowary Todd L Zou Wei |
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Affiliation: | a Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada K1A 0R6 b Alberta Ingenuity Centre for Carbohydrate Science and Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2 |
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Abstract: | 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. |
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Keywords: | Synthesis C-Glycoside Amino acid Nucleoside Galactosyltransferase Inhibitors |
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