Molecular rules for chemo- and regio-selectivity of Candida antarctica lipase B in peptide acylation reactions
Identifieur interne : 000376 ( Main/Exploration ); précédent : 000375; suivant : 000377Molecular rules for chemo- and regio-selectivity of Candida antarctica lipase B in peptide acylation reactions
Auteurs : Florent Ferrari ; Cedric Paris [France] ; Bernard Maigret [France] ; Christelle Bidouil ; Stéphane Delaunay [France] ; Catherine Humeau [France] ; Isabelle Chevalot [France]Source :
- Journal of Molecular Catalysis B: Enzymatic [ 1381-1177 ] ; 2014-03.
Abstract
The chemo- and regio-selectivity of the lipase B of Candida antarctica (CALB) in peptide acylation by oleic acid was investigated combining experimental and theoretical methodologies. Molecular dynamics and docking simulations were performed to study the selectivity of CALB toward the dipeptide Lysine-Serine at the molecular level. To this end, a model that mimics the acyl-enzyme system was built from CALB crystallographic structure and optimized then to be used as docking target. One main orientation of the peptide within the catalytic cavity was obtained. The lysine side chain was observed to enter the cavity, placing the s-amino group as to be acylated near the catalytic residues. This result was consistent with the N-acylation experimentally observed, showing the robustness of the model. Docking simulations were then applied to the peptides Lysine-Tyrosine-Serine, Serine-Tyrosine-Lysine and Leucine-GlutamineLysine-Tryptophan aiming to predict the selectivity of the reaction. Whatever the peptidic sequence and its constitutive amino acids, the models suggested the preferential N-acylation of the lysine side chain. These theoretical results were in perfect accordance with experimental data showing that Ns-oleoyl-Lys derivatives were the major products.
Url:
DOI: 10.1016/j.molcatb.2013.12.007
Affiliations:
Links toward previous steps (curation, corpus...)
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- to stream Main, to step Curation: 000376
Le document en format XML
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<orgName>Laboratoire d'Ingénierie des Biomolécules</orgName>
<orgName type="acronym">LIBio</orgName>
<date type="start">2012-01-01</date>
<desc><address><addrLine>Université de Lorraine - ENSAIA, 2 avenue de la Forêt de Haye - TSA 40602, 54518 Vandœuvre-lès-Nancy Cedex</addrLine>
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<orgName>Université de Lorraine</orgName>
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<date type="start">2012-01-01</date>
<desc><address><addrLine>34 cours Léopold - CS 25233 - 54052 Nancy cedex</addrLine>
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</address>
<ref type="url">http://www.univ-lorraine.fr/</ref>
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</org>
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<country>France</country>
<placeName><settlement type="city">Nancy</settlement>
<settlement type="city">Metz</settlement>
<region type="region" nuts="2">Grand Est</region>
<region type="old region" nuts="2">Lorraine (région)</region>
</placeName>
<orgName type="university">Université de Lorraine</orgName>
</affiliation>
</author>
<author><name sortKey="Chevalot, Isabelle" sort="Chevalot, Isabelle" uniqKey="Chevalot I" first="Isabelle" last="Chevalot">Isabelle Chevalot</name>
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<orgName>Laboratoire Réactions et Génie des Procédés</orgName>
<orgName type="acronym">LRGP</orgName>
<date type="start">2013-01-01</date>
<desc><address><addrLine>Université de Lorraine - ENSIC, 1 rue de Grandville BP 20451, 54001 Nancy Cedex</addrLine>
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</address>
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<orgName>Université de Lorraine</orgName>
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<desc><address><addrLine>34 cours Léopold - CS 25233 - 54052 Nancy cedex</addrLine>
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<orgName>Centre National de la Recherche Scientifique</orgName>
<orgName type="acronym">CNRS</orgName>
<date type="start">1939-10-19</date>
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<country>France</country>
<placeName><settlement type="city">Nancy</settlement>
<settlement type="city">Metz</settlement>
<region type="region" nuts="2">Grand Est</region>
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<idno type="DOI">10.1016/j.molcatb.2013.12.007</idno>
<series><title level="j">Journal of Molecular Catalysis B: Enzymatic</title>
<idno type="ISSN">1381-1177</idno>
<imprint><date type="datePub">2014-03</date>
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<front><div type="abstract" xml:lang="en">The chemo- and regio-selectivity of the lipase B of Candida antarctica (CALB) in peptide acylation by oleic acid was investigated combining experimental and theoretical methodologies. Molecular dynamics and docking simulations were performed to study the selectivity of CALB toward the dipeptide Lysine-Serine at the molecular level. To this end, a model that mimics the acyl-enzyme system was built from CALB crystallographic structure and optimized then to be used as docking target. One main orientation of the peptide within the catalytic cavity was obtained. The lysine side chain was observed to enter the cavity, placing the s-amino group as to be acylated near the catalytic residues. This result was consistent with the N-acylation experimentally observed, showing the robustness of the model. Docking simulations were then applied to the peptides Lysine-Tyrosine-Serine, Serine-Tyrosine-Lysine and Leucine-GlutamineLysine-Tryptophan aiming to predict the selectivity of the reaction. Whatever the peptidic sequence and its constitutive amino acids, the models suggested the preferential N-acylation of the lysine side chain. These theoretical results were in perfect accordance with experimental data showing that Ns-oleoyl-Lys derivatives were the major products.</div>
</front>
</TEI>
<affiliations><list><country><li>France</li>
</country>
<region><li>Grand Est</li>
<li>Lorraine (région)</li>
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<li>Nancy</li>
</settlement>
<orgName><li>Université de Lorraine</li>
</orgName>
</list>
<tree><noCountry><name sortKey="Bidouil, Christelle" sort="Bidouil, Christelle" uniqKey="Bidouil C" first="Christelle" last="Bidouil">Christelle Bidouil</name>
<name sortKey="Ferrari, Florent" sort="Ferrari, Florent" uniqKey="Ferrari F" first="Florent" last="Ferrari">Florent Ferrari</name>
</noCountry>
<country name="France"><region name="Grand Est"><name sortKey="Paris, Cedric" sort="Paris, Cedric" uniqKey="Paris C" first="Cedric" last="Paris">Cedric Paris</name>
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<name sortKey="Chevalot, Isabelle" sort="Chevalot, Isabelle" uniqKey="Chevalot I" first="Isabelle" last="Chevalot">Isabelle Chevalot</name>
<name sortKey="Delaunay, Stephane" sort="Delaunay, Stephane" uniqKey="Delaunay S" first="Stéphane" last="Delaunay">Stéphane Delaunay</name>
<name sortKey="Humeau, Catherine" sort="Humeau, Catherine" uniqKey="Humeau C" first="Catherine" last="Humeau">Catherine Humeau</name>
<name sortKey="Maigret, Bernard" sort="Maigret, Bernard" uniqKey="Maigret B" first="Bernard" last="Maigret">Bernard Maigret</name>
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