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==Structure of haloalcohol dehalogenase HheC of Agrobacterium radiobacter AD1 in complex with (R)-para-nitro styrene oxide, with a water molecule in the halide-binding site==
==Structure of haloalcohol dehalogenase HheC of Agrobacterium radiobacter AD1 in complex with (R)-para-nitro styrene oxide, with a water molecule in the halide-binding site==
<StructureSection load='1zmt' size='340' side='right' caption='[[1zmt]], [[Resolution|resolution]] 1.70&Aring;' scene=''>
<StructureSection load='1zmt' size='340' side='right'caption='[[1zmt]], [[Resolution|resolution]] 1.70&Aring;' scene=''>
== Structural highlights ==
== Structural highlights ==
<table><tr><td colspan='2'>[[1zmt]] is a 4 chain structure with sequence from [http://en.wikipedia.org/wiki/"achromobacter_radiobacter"_(beijerinck_and_van_delden_1902)_bergey_et_al._1934 "achromobacter radiobacter" (beijerinck and van delden 1902) bergey et al. 1934]. Full crystallographic information is available from [http://oca.weizmann.ac.il/oca-bin/ocashort?id=1ZMT OCA]. For a <b>guided tour on the structure components</b> use [http://oca.weizmann.ac.il/oca-docs/fgij/fg.htm?mol=1ZMT FirstGlance]. <br>
<table><tr><td colspan='2'>[[1zmt]] is a 4 chain structure with sequence from [https://en.wikipedia.org/wiki/Agrobacterium_tumefaciens Agrobacterium tumefaciens]. Full crystallographic information is available from [http://oca.weizmann.ac.il/oca-bin/ocashort?id=1ZMT OCA]. For a <b>guided tour on the structure components</b> use [https://proteopedia.org/fgij/fg.htm?mol=1ZMT FirstGlance]. <br>
</td></tr><tr id='ligand'><td class="sblockLbl"><b>[[Ligand|Ligands:]]</b></td><td class="sblockDat"><scene name='pdbligand=RNO:(R)-PARA-NITROSTYRENE+OXIDE'>RNO</scene></td></tr>
</td></tr><tr id='method'><td class="sblockLbl"><b>[[Empirical_models|Method:]]</b></td><td class="sblockDat" id="methodDat">X-ray diffraction, [[Resolution|Resolution]] 1.7&#8491;</td></tr>
<tr id='related'><td class="sblockLbl"><b>[[Related_structure|Related:]]</b></td><td class="sblockDat">[[1zmo|1zmo]], [[1zo8|1zo8]]</td></tr>
<tr id='ligand'><td class="sblockLbl"><b>[[Ligand|Ligands:]]</b></td><td class="sblockDat" id="ligandDat"><scene name='pdbligand=RNO:(R)-PARA-NITROSTYRENE+OXIDE'>RNO</scene></td></tr>
<tr id='resources'><td class="sblockLbl"><b>Resources:</b></td><td class="sblockDat"><span class='plainlinks'>[http://oca.weizmann.ac.il/oca-docs/fgij/fg.htm?mol=1zmt FirstGlance], [http://oca.weizmann.ac.il/oca-bin/ocaids?id=1zmt OCA], [http://pdbe.org/1zmt PDBe], [http://www.rcsb.org/pdb/explore.do?structureId=1zmt RCSB], [http://www.ebi.ac.uk/pdbsum/1zmt PDBsum], [http://prosat.h-its.org/prosat/prosatexe?pdbcode=1zmt ProSAT]</span></td></tr>
<tr id='resources'><td class="sblockLbl"><b>Resources:</b></td><td class="sblockDat"><span class='plainlinks'>[https://proteopedia.org/fgij/fg.htm?mol=1zmt FirstGlance], [http://oca.weizmann.ac.il/oca-bin/ocaids?id=1zmt OCA], [https://pdbe.org/1zmt PDBe], [https://www.rcsb.org/pdb/explore.do?structureId=1zmt RCSB], [https://www.ebi.ac.uk/pdbsum/1zmt PDBsum], [https://prosat.h-its.org/prosat/prosatexe?pdbcode=1zmt ProSAT]</span></td></tr>
</table>
</table>
== Function ==
[https://www.uniprot.org/uniprot/Q93D82_RHIRD Q93D82_RHIRD]
== Evolutionary Conservation ==
== Evolutionary Conservation ==
[[Image:Consurf_key_small.gif|200px|right]]
[[Image:Consurf_key_small.gif|200px|right]]
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</jmol>, as determined by [http://consurfdb.tau.ac.il/ ConSurfDB]. You may read the [[Conservation%2C_Evolutionary|explanation]] of the method and the full data available from [http://bental.tau.ac.il/new_ConSurfDB/main_output.php?pdb_ID=1zmt ConSurf].
</jmol>, as determined by [http://consurfdb.tau.ac.il/ ConSurfDB]. You may read the [[Conservation%2C_Evolutionary|explanation]] of the method and the full data available from [http://bental.tau.ac.il/new_ConSurfDB/main_output.php?pdb_ID=1zmt ConSurf].
<div style="clear:both"></div>
<div style="clear:both"></div>
<div style="background-color:#fffaf0;">
== Publication Abstract from PubMed ==
Halo alcohol dehalogenase HheC catalyzes the highly enantioselective dehalogenation of vicinal halo alcohols to epoxides, as well as the reverse reaction, the enantioselective and beta-regioselective nucleophilic ring opening of epoxides by pseudo-halides such as azide and cyanide. To investigate this latter reaction, we determined X-ray structures of complexes of HheC with the favored and unfavored enantiomers of para-nitrostyrene oxide. The aromatic parts of the two enantiomers bind in a very similar way, but the epoxide ring of the unfavored (S)-enantiomer binds in a nonproductive inverted manner, with the epoxide oxygen and Cbeta atom positions interchanged with respect to those of the favored (R)-enantiomer. The calculated difference in relative Gibbs binding energy is in agreement with the observed loss of a single hydrogen bond in the S bound state with respect to the R bound state. Our results indicate that it is the nonproductive binding of the unfavored (S)-enantiomer, rather than the difference in affinity for the two enantiomers, that allows HheC to catalyze the azide-mediated ring opening of para-nitrostyrene oxide with high enantioselectivity. This work represents a rare opportunity to explain the enantioselectivity of an enzymatic reaction by comparison of crystallographic data on the binding of both the favored and unfavored enantiomers.


Structural basis for the enantioselectivity of an epoxide ring opening reaction catalyzed by halo alcohol dehalogenase HheC.,de Jong RM, Tiesinga JJ, Villa A, Tang L, Janssen DB, Dijkstra BW J Am Chem Soc. 2005 Sep 28;127(38):13338-43. PMID:16173767<ref>PMID:16173767</ref>
==See Also==
 
*[[Dehalogenase 3D structures|Dehalogenase 3D structures]]
From MEDLINE&reg;/PubMed&reg;, a database of the U.S. National Library of Medicine.<br>
</div>
<div class="pdbe-citations 1zmt" style="background-color:#fffaf0;"></div>
== References ==
<references/>
__TOC__
__TOC__
</StructureSection>
</StructureSection>
[[Category: Dijkstra, B W]]
[[Category: Agrobacterium tumefaciens]]
[[Category: Janssen, D B]]
[[Category: Large Structures]]
[[Category: Jong, R M.de]]
[[Category: Dijkstra BW]]
[[Category: Tang, L]]
[[Category: Janssen DB]]
[[Category: Tiesinga, J J.W]]
[[Category: Tang L]]
[[Category: Villa, A]]
[[Category: Tiesinga JJW]]
[[Category: Enantioselectivity]]
[[Category: Villa A]]
[[Category: Epoxide catalysis]]
[[Category: De Jong RM]]
[[Category: Haloalcohol dehalogenase]]
[[Category: Halohydrin dehalogenase]]
[[Category: Lyase]]

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