Journal
CHEMISTRY & BIOLOGY
Volume 17, Issue 12, Pages 1356-1366Publisher
CELL PRESS
DOI: 10.1016/j.chembiol.2010.10.014
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Funding
- Slovak Research and Development Agency [RPEU-0012-06]
- ERDF (Centre of Excellence for Exploitation of Informational Biomacromolecules in the Disease Prevention and Improvement of Quality of Life)
- European Commission [LSHP-CT-2005-018923 NM4TB]
- AIDS-FIRCA [TW 006487]
- Alberta Ingenuity Centre for Carbohydrate Science
- Natural Sciences and Engineering Research Council of Canada
- Agence Nationale de la Recherche ANR [JCJC06_140075]
- Rennes Metropoles
- NIH
- NIAID
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UDP-galactofuranose (UDP-Galf) is a substrate for two types of enzymes, UDP-galactopyranose mutase and galactofuranosyltransferases, which are present in many pathogenic organisms but absent from mammals. In particular, these enzymes are involved in the biosynthesis of cell wall galactan, a polymer essential for the survival of the causative agent of tuberculosis, Mycobacterium tuberculosis. We describe here the synthesis of derivatives of UDP-Galf modified at C-5 and C-6 using a chemoenzymatic route. In cell-free assays, these compounds prevented the formation of mycobacterial galactan, via the production of short dead-end intermediates resulting from their incorporation into the growing oligosaccharide chain. Modified UDP-furanoses thus constitute novel probes for the study of the two classes of enzymes involved in mycobacterial galactan assembly, and studies with these compounds may ultimately facilitate the future development of new therapeutic agents against tuberculosis.
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