Synthetic analogues of SB-219383. Novel C-glycosyl peptides as inhibitors of tyrosyl tRNA synthetase

Novel inhibitors of bacterial tyrosyl tRNA synthetase have been synthesised in which the cyclic hydroxylamine moiety of SB-219383 is replaced by C-pyranosyl derivatives. Potent and selective inhibition of bacterial tyrosyl tRNA synthetase was obtained. Novel inhibitors of bacterial tyrosyl tRNA synt...

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Published in:Bioorganic & medicinal chemistry letters 2001-03, Vol.11 (5), p.711-714
Main Authors: Brown, Pamela, Eggleston, Drake S., Haltiwanger, R.Curtis, Jarvest, Richard L., Mensah, Lucy, O'Hanlon, Peter J., Pope, Andrew J.
Format: Article
Language:English
Subjects:
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Bacterial Proteins - chemistry
Bacterial Proteins - metabolism
Biological and medical sciences
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Bridged Bicyclo Compounds, Heterocyclic - pharmacology
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - pharmacology
Furans - chemistry
Furans - pharmacology
Medical sciences
Models, Molecular
Molecular Structure
Pharmacology. Drug treatments
Pyrans - chemistry
Staphylococcus aureus - enzymology
Staphylococcus aureus - metabolism
Tyrosine-tRNA Ligase - antagonists & inhibitors
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Summary:Novel inhibitors of bacterial tyrosyl tRNA synthetase have been synthesised in which the cyclic hydroxylamine moiety of SB-219383 is replaced by C-pyranosyl derivatives. Potent and selective inhibition of bacterial tyrosyl tRNA synthetase was obtained. Novel inhibitors of bacterial tyrosyl tRNA synthetase have been synthesised in which the cyclic hydroxylamine moiety of SB-219383 is replaced by C-pyranosyl derivatives. The l-arabinosederivative is a potent and selective inhibitor.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(01)00039-7