Search results for "Hemithioacetal"

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Multiscale Simulations of SARS-CoV-2 3CL Protease Inhibition with Aldehyde Derivatives. Role of Protein and Inhibitor Conformational Changes in the R…

2021

We here investigate the mechanism of SARS-CoV-2 3CL protease inhibition by one of the most promising families of inhibitors, those containing an aldehyde group as a warhead. These compounds are covalent inhibitors that inactivate the protease, forming a stable hemithioacetal complex. Inhibitor 11a is a potent inhibitor that has been already tested in vitro and in animals. Using a combination of classical and QM/MM simulations, we determined the binding mode of the inhibitor into the active site and the preferred rotameric state of the catalytic histidine. In the noncovalent complex, the aldehyde group is accommodated into the oxyanion hole formed by the NH main-chain groups of residues 143 …

Stereochemistrymedicine.medical_treatment010402 general chemistry01 natural sciencesAldehydeQM/MMCatalysisQM/MM3CL proteasechemistry.chemical_compoundminimum free energy pathNucleophileinhibitorsmedicineconformational changesaldehyde derivativeschemistry.chemical_classificationProteasebiology010405 organic chemistrySARS-CoV-2Active siteHemithioacetalGeneral Chemistry0104 chemical scienceschemistryCovalent bondbiology.proteinOxyanion holeResearch ArticleACS Catalysis
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Multiscale Simulations of SARS-CoV-2 3CL Protease Inhibition with Aldehyde Derivatives. Role of Protein and Inhibitor Conformational Dynamics in the …

2020

<p>We here investigate the mechanism of SARS-CoV-2 3CL protease inhibition by one of the most promising families of inhibitors, those containing an aldehyde group as warhead. These compounds are covalent inhibitors that inactivate the protease forming a stable hemithioacetal complex. Inhibitor 11a is a potent inhibitor that has been already tested in vitro and in animals. Using a combination of classical and QM/MM simulations we determined the binding mode of the inhibitor into the active site and the preferred rotameric state of the catalytic histidine. In the noncovalent complex the aldehyde group is accommodated into the oxyanion hole formed by the NH main chain groups of residues …

chemistry.chemical_classificationProteasebiologyStereochemistrymedicine.medical_treatmentActive siteHemithioacetalAldehydechemistry.chemical_compoundchemistryNucleophileCovalent bondmedicinebiology.proteinOxyanion holeHistidine
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