Molecular rules for chemo- and regio-selectivity of Candida antarctica lipase B in peptide acylation reactions
Identifieur interne : 000E37 ( Main/Exploration ); précédent : 000E36; suivant : 000E38Molecular rules for chemo- and regio-selectivity of Candida antarctica lipase B in peptide acylation reactions
Auteurs : Florent Ferrari [France] ; Cédric Paris [France] ; Bernard Maigret [France] ; Christelle Bidouil [France] ; Stephane Delaunay [France] ; Catherine Humeau [France] ; Isabelle Chevalot [France]Source :
- Journal of molecular catalysis. B, Enzymatic [ 1381-1177 ] ; 2014.
Descripteurs français
- Pascal (Inist)
English descriptors
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 ε-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-Glutamine-Lysine-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 Nε-oleoyl-Lys derivatives were the major products.
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Affiliations:
- France
- Grand Est, Lorraine (région)
- Vandœuvre-lès-Nancy
- Université Henri Poincaré, Université de Lorraine
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wicri:level="4"><inist:fA14 i1="01"><s1>Laboratoire Réactions et Génie des Procédés, CNRS UMR-7274, Université de Lorraine, 2 av. de la Forêt d'Hayc</s1><s2>54500 Vandœuvre-lès-Nancy</s2><s3>FRA</s3><sZ>1 aut.</sZ><sZ>5 aut.</sZ><sZ>7 aut.</sZ></inist:fA14><country>France</country><placeName><region type="region" nuts="2">Grand Est</region><region type="old region" nuts="2">Lorraine (région)</region><settlement type="city">Vandœuvre-lès-Nancy</settlement></placeName><orgName type="university">Université de Lorraine</orgName></affiliation></author></analytic><series><title level="j" type="main">Journal of molecular catalysis. B, Enzymatic</title><title level="j" type="abbreviated">J. mol. catal., B Enzym.</title><idno type="ISSN">1381-1177</idno><imprint><date when="2014">2014</date></imprint></series></biblStruct></sourceDesc><seriesStmt><title level="j" type="main">Journal of molecular catalysis. B, Enzymatic</title><title level="j" type="abbreviated">J. mol. catal., B Enzym.</title><idno type="ISSN">1381-1177</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Acylation</term><term>Peptides</term><term>Selectivity</term><term>Triacylglycerol lipase</term><term>candida antarctica</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Sélectivité</term><term>Triacylglycerol lipase</term><term>Peptide</term><term>Acylation</term><term>Candida antarctica</term></keywords></textClass></profileDesc></teiHeader><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 ε-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-Glutamine-Lysine-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 Nε-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></region><settlement><li>Vandœuvre-lès-Nancy</li></settlement><orgName><li>Université Henri Poincaré</li><li>Université de Lorraine</li></orgName></list><tree><country name="France"><region name="Grand Est"><name sortKey="Ferrari, Florent" sort="Ferrari, Florent" uniqKey="Ferrari F" first="Florent" last="Ferrari">Florent Ferrari</name></region><name sortKey="Bidouil, Christelle" sort="Bidouil, Christelle" uniqKey="Bidouil C" first="Christelle" last="Bidouil">Christelle Bidouil</name><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="Stephane" last="Delaunay">Stephane 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><name sortKey="Paris, Cedric" sort="Paris, Cedric" uniqKey="Paris C" first="Cédric" last="Paris">Cédric Paris</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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