Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 19, Pages 6326-6336Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo100928g
Keywords
-
Categories
Funding
- Royal Society
- Lister Institute
- Medical Research Council
- Wellcome Trust [081569/Z/06/Z]
- Personal Research Chair
- Wellcome Trust [081569/Z/06/Z] Funding Source: Wellcome Trust
- MRC [G0802079, G0500590] Funding Source: UKRI
- Medical Research Council [G0802079, G0500590] Funding Source: researchfish
Ask authors/readers for more resources
Aiming at developing inhibitors of mannosyltransferases, the enzymes that participate in the biosynthesis of the cell envelope of Mycobacterium tuberculosis, the synthesis of a range of designed triazole-linked 1,6-oligomannosides up to a hexadecamer has been accomplished by a modular approach centered on the Cu(I)-catalyzed azide-alkyne cycloaddition as key process. The efficiency and fidelity of the cycloaddition are substantiated by high yields (76-96%) and exclusive formation of the expected 1,4-disubstituted triazole ring in all oligomer assembling reactions. Key features of oligomers thus prepared are the anomeric carbon-carbon bond of all mannoside residues and the 6-deoxymannoside capping residue. Suitable bioassays with dimer, tetramer, hexamer, octamer, decamer, and hexadecamer showed variable inhibitor activity against mycobacterial alpha-(1,6)-mannosyltransferases, the highest activity (IC50 = 0.14-0.22 mM) being registered with the hexamannoside and octamannoside.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available