Abstract
Synthetic analogues of the microbial metabolite SB-219383 have been synthesised with defined stereochemistry. Densely functionalised hydroxylamine containing amino acids were prepared by the addition of a glycine anion equivalent to sugar-derived cyclic nitrones. One of four stereoisomeric dipeptides incorporating these novel amino acids was found to be a potent and selective inhibitor of bacterial tyrosyl tRNA synthetase, suggesting analogous stereochemistry of the natural product.
MeSH terms
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Bacterial Physiological Phenomena
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Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
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Bridged Bicyclo Compounds, Heterocyclic / chemistry*
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Chemistry, Organic
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Enzyme Inhibitors / chemical synthesis
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Enzyme Inhibitors / chemistry*
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Furans / chemical synthesis*
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Furans / chemistry*
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Magnetic Resonance Spectroscopy
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Molecular Structure
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Organic Chemistry Phenomena
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Stereoisomerism
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Tyrosine-tRNA Ligase / antagonists & inhibitors*
Substances
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Bridged Bicyclo Compounds, Heterocyclic
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Enzyme Inhibitors
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Furans
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SB 219383
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Tyrosine-tRNA Ligase