Inhibitors of bacterial tyrosyl tRNA synthetase: synthesis of four stereoisomeric analogues of the natural product SB-219383
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 dipeptide...
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| Published in: | Bioorganic & medicinal chemistry letters Vol. 10; no. 16; pp. 1811 - 1814 |
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| Main Authors: | , , , , , , , |
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| 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. |
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| AbstractList | 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. |
| Author | Mensah, Lucy M O'Hanlon, Peter J Copley, Royston C.B Hamprecht, Dieter W Jarvest, Richard L Berge, John M Pope, Andrew J Eggleston, Drake S |
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| Cites_doi | 10.7164/antibiotics.53.351 10.1016/S0008-6215(00)85950-9 10.1016/S0968-0896(99)00192-3 10.7164/antibiotics.53.345 |
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| Keywords | Stereoisomer Peptides Enzyme Enzyme inhibitor Tyrosine-tRNA ligase In vitro Structure activity relation Ligases Piperidine derivatives Dipeptides Bacteria Micrococcales Micrococcaceae Antibacterial agent Chemical synthesis Carbon-oxygen ligases Triol Organic hydroxylamine Staphylococcus aureus |
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| References | 11.421(2) Å 1.023; Δ Data collection: Nonius MACH3 diffractometer, GX21 rotating copper anode generator, graphite monochromator, 293 K for the >bonded atom For examples of sugar derived nitrones see e. g.: Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, Z.; Sztaricskai, F. 5385. Dondoni, A.; Junquera, F.; Merchán, L.; Merino, P.; Scherrmann, M.-C.; Tejero, T. Cu Δ scans For examples of additions of organometallics to nitrones, see e.g.: Lantos, I.; Flisak, J.; Liu, L.; Matsuoka, R.; Mendelson, W.; Stevenson, D.; Tubman, K.; Tucker, L.; Zhang, W.-Y.; Adams, J.; Sorenson, M.; Garigipati, R.; Erhardt, K.; Ross, S. mm extinction coefficient=0.00113(9); absolute structure parameter (Flack)=0.00(4). Crystallographic data for this structure has been deposited with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained, free of charge, on application to the Director, CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk). Mg m 4255. 30.105(5) 4220 1.54178 Å)=1.019 ( 2663. Ghosez, L.; Antoine, J.-P.; Deffense, E.; Navarro, M.; Libert, V.; O'Donnell, M. J.; Bruder, W. A.; Willey, K.; Wojciechowski, K. 0.9206; decay correction, four standard reflections, maximum variation=13.0 , 103.431(12) 8.7694(16) ° 2 522.70, monoclinic, C2 (no. 5) 4 0.0325. Solution and refinement: SHELXTL V5.10 IRIX package; direct methods; full-matrix least-squares refinement on X-ray crystal structure determination of the opposite enantiomer to 2932.7(10) Å 0.103 e Å 1863. 58.91 4794 4467. Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Kiso, Hasegawa (BIB7) 1976; 52 O'Donnell, M. J.; Polt, R. L. 5623. H Stefanska, Coates, Mensah, Pope, Ready, Warr (BIB1) 2000; 53 DMSO- Berge, J. M.; Broom, N. J. P.; Houge-Frydrych, C. S. V.; Jarvest, R. L.; Mensah, L. M.; McNair, D. J.; O'Hanlon, P. J.; Pope, A. J.; Rittenhouse, S., submitted for publication. N O 1211. Van den Broek, L. A. G. M. 0.6774 Houge-Frydrych, Readshaw, Bell (BIB3) 2000; 53 0.0434, w 2 (all data)=0.1069 0.148 e Å solution at reduced pressure. Crystal data: colourless blade, 0.63×0.27×0.05 mm; C Si, M coordinates and anisotropic displacement parameters refined for the non-hydrogen atoms; hydrogen atoms in idealised positions, riding or as rigid rotating groups, with isotropic atomic displacement parameters which were an appropriate multiple of Brown, Richardson, Mensah, O'Hanlon, Osborne, Pope, Walker (BIB11) 1999; 7 Rogozhin, Davidovich, Andreev, Mironova, Yurtanov (BIB10) 1974; 8 1 (3545 data with 343 Crystals were grown via the evaporation of a CDCl 5484. Fiumana, A.; Lombardo, M.; Trombini, C. 1.184 Walker, Brown, Forrest, O'Hanlon, Pons (BIB2) 1993 4220. Data reduction: corrections for Lorentz and polarisation effects; psi-scan absorption correction Stefanska (10.1016/S0960-894X(00)00348-6_BIB1) 2000; 53 Houge-Frydrych (10.1016/S0960-894X(00)00348-6_BIB3) 2000; 53 Kiso (10.1016/S0960-894X(00)00348-6_BIB7) 1976; 52 10.1016/S0960-894X(00)00348-6_BIB9 10.1016/S0960-894X(00)00348-6_BIB8 Rogozhin (10.1016/S0960-894X(00)00348-6_BIB10) 1974; 8 Brown (10.1016/S0960-894X(00)00348-6_BIB11) 1999; 7 10.1016/S0960-894X(00)00348-6_BIB6 Walker (10.1016/S0960-894X(00)00348-6_BIB2) 1993 10.1016/S0960-894X(00)00348-6_BIB5 10.1016/S0960-894X(00)00348-6_BIB4 |
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| Snippet | Synthetic analogues of the microbial metabolite SB-219383 have been synthesised with defined stereochemistry. Densely functionalised hydroxylamine containing... |
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| SubjectTerms | Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Bacterial Physiological Phenomena Biological and medical sciences Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis Bridged Bicyclo Compounds, Heterocyclic - chemistry Chemistry, Organic Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Furans - chemical synthesis Furans - chemistry Magnetic Resonance Spectroscopy Medical sciences Molecular Structure Organic Chemistry Phenomena Pharmacology. Drug treatments Stereoisomerism Tyrosine-tRNA Ligase - antagonists & inhibitors |
| Title | Inhibitors of bacterial tyrosyl tRNA synthetase: synthesis of four stereoisomeric analogues of the natural product SB-219383 |
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