4oj8

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{{STRUCTURE_4oj8| PDB=4oj8 | SCENE= }}
 
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===Crystal structure of carbapenem synthase in complex with (3S,5S)-carbapenam===
 
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{{ABSTRACT_PUBMED_24604200}}
 
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==Function==
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==Crystal structure of carbapenem synthase in complex with (3S,5S)-carbapenam==
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[[http://www.uniprot.org/uniprot/CARC_PECCC CARC_PECCC]] Catalyzes the Fe(2+) and alpha-ketoglutarate-dependent conversion of (3S,5S)-carbapenam to (5R)-carbapenem, an essential step in carbapenem antibiotic biosynthesis.<ref>PMID:9402024</ref> <ref>PMID:12848554</ref> <ref>PMID:15174175</ref> <ref>PMID:12611886</ref>
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<StructureSection load='4oj8' size='340' side='right'caption='[[4oj8]], [[Resolution|resolution]] 2.10&Aring;' scene=''>
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== Structural highlights ==
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<table><tr><td colspan='2'>[[4oj8]] is a 3 chain structure with sequence from [https://en.wikipedia.org/wiki/Pectobacterium_carotovorum_subsp._carotovorum Pectobacterium carotovorum subsp. carotovorum]. Full crystallographic information is available from [http://oca.weizmann.ac.il/oca-bin/ocashort?id=4OJ8 OCA]. For a <b>guided tour on the structure components</b> use [https://proteopedia.org/fgij/fg.htm?mol=4OJ8 FirstGlance]. <br>
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</td></tr><tr id='method'><td class="sblockLbl"><b>[[Empirical_models|Method:]]</b></td><td class="sblockDat" id="methodDat">X-ray diffraction, [[Resolution|Resolution]] 2.1&#8491;</td></tr>
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<tr id='ligand'><td class="sblockLbl"><b>[[Ligand|Ligands:]]</b></td><td class="sblockDat" id="ligandDat"><scene name='pdbligand=2TQ:(2S,5S)-7-OXO-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC+ACID'>2TQ</scene>, <scene name='pdbligand=AKG:2-OXOGLUTARIC+ACID'>AKG</scene>, <scene name='pdbligand=FE2:FE+(II)+ION'>FE2</scene>, <scene name='pdbligand=GOL:GLYCEROL'>GOL</scene></td></tr>
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<tr id='resources'><td class="sblockLbl"><b>Resources:</b></td><td class="sblockDat"><span class='plainlinks'>[https://proteopedia.org/fgij/fg.htm?mol=4oj8 FirstGlance], [http://oca.weizmann.ac.il/oca-bin/ocaids?id=4oj8 OCA], [https://pdbe.org/4oj8 PDBe], [https://www.rcsb.org/pdb/explore.do?structureId=4oj8 RCSB], [https://www.ebi.ac.uk/pdbsum/4oj8 PDBsum], [https://prosat.h-its.org/prosat/prosatexe?pdbcode=4oj8 ProSAT]</span></td></tr>
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</table>
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== Function ==
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[https://www.uniprot.org/uniprot/CARC_PECCC CARC_PECCC] Catalyzes the Fe(2+) and alpha-ketoglutarate-dependent conversion of (3S,5S)-carbapenam to (5R)-carbapenem, an essential step in carbapenem antibiotic biosynthesis.<ref>PMID:9402024</ref> <ref>PMID:12848554</ref> <ref>PMID:15174175</ref> <ref>PMID:12611886</ref>
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<div style="background-color:#fffaf0;">
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== Publication Abstract from PubMed ==
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The bicyclic beta-lactam/2-pyrrolidine precursor to all carbapenem antibiotics is biosynthesized by attachment of a carboxymethylene unit to C5 of L-proline followed by beta-lactam ring closure. Carbapenem synthase (CarC), an Fe(II) and 2-(oxo)glutarate (Fe/2OG)-dependent oxygenase, then inverts the C5 configuration. Here we report the structure of CarC in complex with its substrate and biophysical dissection of its reaction to reveal the stereoinversion mechanism. An Fe(IV)-oxo intermediate abstracts the hydrogen (H*) from C5, and tyrosine 165, a residue not visualized in the published structures of CarC lacking bound substrate, donates H* to the opposite face of the resultant radical. The reaction oxidizes the Fe(II) cofactor to Fe(III), limiting wild-type CarC to one turnover, but substitution of the H*-donating tyrosine disables stereoinversion and confers to CarC the capacity for catalytic substrate oxidation.
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==About this Structure==
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Mechanism of the C5 stereoinversion reaction in the biosynthesis of carbapenem antibiotics.,Chang WC, Guo Y, Wang C, Butch SE, Rosenzweig AC, Boal AK, Krebs C, Bollinger JM Jr Science. 2014 Mar 7;343(6175):1140-4. doi: 10.1126/science.1248000. PMID:24604200<ref>PMID:24604200</ref>
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[[4oj8]] is a 3 chain structure. Full crystallographic information is available from [http://oca.weizmann.ac.il/oca-bin/ocashort?id=4OJ8 OCA].
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==Reference==
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From MEDLINE&reg;/PubMed&reg;, a database of the U.S. National Library of Medicine.<br>
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<ref group="xtra">PMID:024604200</ref><references group="xtra"/><references/>
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</div>
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[[Category: Boal, A K.]]
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<div class="pdbe-citations 4oj8" style="background-color:#fffaf0;"></div>
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[[Category: Rosenzweig, A C.]]
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== References ==
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[[Category: 2-oxoglutaric acid]]
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<references/>
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[[Category: Antibiotic biosynthesis]]
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__TOC__
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[[Category: Carbapenam]]
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</StructureSection>
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[[Category: Iron]]
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[[Category: Large Structures]]
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[[Category: Oxidoreductase]]
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[[Category: Pectobacterium carotovorum subsp. carotovorum]]
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[[Category: Oxygenase]]
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[[Category: Boal AK]]
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[[Category: Rosenzweig AC]]

Current revision

Crystal structure of carbapenem synthase in complex with (3S,5S)-carbapenam

PDB ID 4oj8

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