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<StructureSection load='4c5r' size='340' side='right'caption='[[4c5r]], [[Resolution|resolution]] 2.14&Aring;' scene=''>
<StructureSection load='4c5r' size='340' side='right'caption='[[4c5r]], [[Resolution|resolution]] 2.14&Aring;' scene=''>
== Structural highlights ==
== Structural highlights ==
<table><tr><td colspan='2'>[[4c5r]] is a 4 chain structure with sequence from [http://en.wikipedia.org/wiki/Chinese_yew Chinese yew]. Full crystallographic information is available from [http://oca.weizmann.ac.il/oca-bin/ocashort?id=4C5R OCA]. For a <b>guided tour on the structure components</b> use [http://oca.weizmann.ac.il/oca-docs/fgij/fg.htm?mol=4C5R FirstGlance]. <br>
<table><tr><td colspan='2'>[[4c5r]] is a 4 chain structure with sequence from [https://en.wikipedia.org/wiki/Taxus_chinensis Taxus chinensis]. Full crystallographic information is available from [http://oca.weizmann.ac.il/oca-bin/ocashort?id=4C5R OCA]. For a <b>guided tour on the structure components</b> use [https://proteopedia.org/fgij/fg.htm?mol=4C5R FirstGlance]. <br>
</td></tr><tr id='ligand'><td class="sblockLbl"><b>[[Ligand|Ligands:]]</b></td><td class="sblockDat"><scene name='pdbligand=BQ7:(3S)-3-AMINO-2,2-DIFLUORO-3-PHENYLPROPANOIC+ACID'>BQ7</scene>, <scene name='pdbligand=GOL:GLYCEROL'>GOL</scene></td></tr>
</td></tr><tr id='ligand'><td class="sblockLbl"><b>[[Ligand|Ligands:]]</b></td><td class="sblockDat" id="ligandDat"><scene name='pdbligand=BQ7:(3S)-3-AMINO-2,2-DIFLUORO-3-PHENYLPROPANOIC+ACID'>BQ7</scene>, <scene name='pdbligand=GOL:GLYCEROL'>GOL</scene>, <scene name='pdbligand=MDO:{2-[(1S)-1-AMINOETHYL]-4-METHYLIDENE-5-OXO-4,5-DIHYDRO-1H-IMIDAZOL-1-YL}ACETIC+ACID'>MDO</scene></td></tr>
<tr id='NonStdRes'><td class="sblockLbl"><b>[[Non-Standard_Residue|NonStd Res:]]</b></td><td class="sblockDat"><scene name='pdbligand=MDO:{2-[(1S)-1-AMINOETHYL]-4-METHYLIDENE-5-OXO-4,5-DIHYDRO-1H-IMIDAZOL-1-YL}ACETIC+ACID'>MDO</scene></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=4c5r FirstGlance], [http://oca.weizmann.ac.il/oca-bin/ocaids?id=4c5r OCA], [https://pdbe.org/4c5r PDBe], [https://www.rcsb.org/pdb/explore.do?structureId=4c5r RCSB], [https://www.ebi.ac.uk/pdbsum/4c5r PDBsum], [https://prosat.h-its.org/prosat/prosatexe?pdbcode=4c5r ProSAT]</span></td></tr>
<tr id='related'><td class="sblockLbl"><b>[[Related_structure|Related:]]</b></td><td class="sblockDat">[[4c5s|4c5s]], [[4c5t|4c5t]], [[4c5u|4c5u]], [[4c5v|4c5v]]</td></tr>
<tr id='activity'><td class="sblockLbl"><b>Activity:</b></td><td class="sblockDat"><span class='plainlinks'>[http://en.wikipedia.org/wiki/Phenylalanine_ammonia-lyase Phenylalanine ammonia-lyase], with EC number [http://www.brenda-enzymes.info/php/result_flat.php4?ecno=4.3.1.24 4.3.1.24] </span></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=4c5r FirstGlance], [http://oca.weizmann.ac.il/oca-bin/ocaids?id=4c5r OCA], [http://pdbe.org/4c5r PDBe], [http://www.rcsb.org/pdb/explore.do?structureId=4c5r RCSB], [http://www.ebi.ac.uk/pdbsum/4c5r PDBsum], [http://prosat.h-its.org/prosat/prosatexe?pdbcode=4c5r ProSAT]</span></td></tr>
</table>
</table>
<div style="background-color:#fffaf0;">
== Function ==
== Publication Abstract from PubMed ==
[[https://www.uniprot.org/uniprot/PAM_TAXWC PAM_TAXWC]] Phenylalanine aminomutase that catalyzes the rearrangement of L-phenylalanine to R-beta-phenylalanine. Catalyzes the first commited step in the biosynthesis of the side chain of the alkaloid taxol (paclitaxel), a widely-used compound with antitumor activity. Has also low phenylalanine ammonia-lyase activity and can catalyze the amination of trans-cinnamate.<ref>PMID:15878763</ref> <ref>PMID:22113970</ref> <ref>PMID:24786474</ref>  
Phenylalanine-2,3-aminomutase (PAM) from Taxus chinensis, a 4-methylidene-imidazole-5-one (MIO)-dependent enzyme, catalyzes the reversible conversion of (S)-alpha-phenylalanine into (R)-beta-phenylalanine via trans-cinnamic acid. The enzyme also catalyzes the direct addition of ammonia to trans-cinnamic acid, a reaction that can be used for the preparation of beta-amino acids, which occur as frequent constituents of bioactive compounds. Different hypotheses have been formulated to explain the stereochemistry of the PAM-catalyzed reaction, but structural evidence for these hypotheses is lacking. Furthermore, it remains unclear how the PAM MIO group is formed from the three-amino acid (A-S-G) sequence motif. For these reasons, we elucidated PAM three-dimensional (3D) structures with a bound (R)-beta-phenylalanine analogue and with bound trans-cinnamic acid. In addition, 3D structures of the (inactive) Y322A and N231A mutants of PAM were elucidated, which were found to be MIO-less. We conclude that the stereochemistry of the PAM-catalyzed reaction originates from the enzyme's ability to bind trans-cinnamic acid in two different orientations, with either the si,si face or the re,re face directed toward the MIO group, as evidenced by two distinct carboxylate binding modes. The results also suggest that the N231 side chain promotes MIO group formation by increasing the nucleophilicity of the G177 N atom through acidification of the amide proton.
 
Structural Investigations into the Stereochemistry and Activity of a Phenylalanine-2,3-aminomutase from Taxus chinensis.,Wybenga GG, Szymanski W, Wu B, Feringa BL, Janssen DB, Dijkstra BW Biochemistry. 2014 May 12. PMID:24786474<ref>PMID:24786474</ref>
 
From MEDLINE&reg;/PubMed&reg;, a database of the U.S. National Library of Medicine.<br>
</div>
<div class="pdbe-citations 4c5r" style="background-color:#fffaf0;"></div>


==See Also==
==See Also==
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__TOC__
__TOC__
</StructureSection>
</StructureSection>
[[Category: Chinese yew]]
[[Category: Large Structures]]
[[Category: Large Structures]]
[[Category: Phenylalanine ammonia-lyase]]
[[Category: Taxus chinensis]]
[[Category: Dijkstra, B W]]
[[Category: Dijkstra BW]]
[[Category: Feringa, B L]]
[[Category: Feringa BL]]
[[Category: Janssen, D B]]
[[Category: Janssen DB]]
[[Category: Szymanski, W]]
[[Category: Szymanski W]]
[[Category: Wu, B]]
[[Category: Wu B]]
[[Category: Wybenga, G G]]
[[Category: Wybenga GG]]
[[Category: Lyase]]

Revision as of 17:28, 7 September 2022

Structural Investigations into the Stereochemistry and Activity of a Phenylalanine-2,3-Aminomutase from Taxus chinensis

4c5r, resolution 2.14Å

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