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MECHANISTIC STUDY OF THE BIOSYNTHESIS OF R-PHENYLACETYLCARBINOL BY ACETOHYDROXYACID SYNTHASE ENZYME USING HYBRID QUANTUM MECHANICS/MOLECULAR MECHANICS SIMULATIONS

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dc.creatorOMAR BLAS ALVARADO CARRIPAN
dc.date2021
dc.date.accessioned2025-01-10T15:28:32Z
dc.date.available2025-01-10T15:28:32Z
dc.date.issued2021
dc.description.abstractTHE BIOSYNTHESIS OF R-PHENYLACETYLCARBINOL (R-PAC) BY THE ACETOHYDROXY ACID SYNTHASE, (AHAS) IS ADDRESSED BY MOLECULAR DYNAMICS SIMULATIONS (MD), HYBRID QUANTUM MECHANICS/MOLECULAR MECHANICS (QM/MM), AND QM/MM FREE ENERGY CALCULATIONS. THE RESULTS SHOW THE REACTION STARTS WITH THE NUCLEOPHILIC ATTACK OF THE C2? ATOM OF THE HETHDP INTERMEDIATE ON THE C? ATOM OF THE CARBONYL GROUP OF BENZALDEHYDE SUBSTRATE VIA THE FORMATION OF A TRANSITION STATE (TS1) WITH THE HETHDP INTERMEDIATE UNDER 4-AMINOPYRIMIDIUM (APH+) FORM. THE CALCULATED ACTIVATION FREE ENERGY FOR THIS STEP IS 17.4 KCAL MOL-1 AT 27 °C. FROM THIS POINT, THE REACTION CONTINUES WITH THE ABSTRACTION OF H? ATOM OF THE HETHDP INTERMEDIATE BY THE O? ATOM OF BENZALDEHYDE TO FORM THE INTERMEDIATE I. THE REACTION IS COMPLETED WITH THE CLEAVAGE OF THE BOND C2?-C2 TO FORM THE PRODUCT R-PAC AND TO REGENERATE THE YLIDE INTERMEDIATE UNDER THE APH+ FORM, ALLOWING IN THIS WAY TO REINITIATE TO THE CATALYTIC CYCLE ONCE MORE. THE CALCULATED ACTIVATION BARRIER FOR THIS LAST STEP IS 15.9 KCAL MOL-1 AT 27 °C.
dc.formatapplication/pdf
dc.identifier.doi10.1016/j.abb.2021.108849
dc.identifier.issn1096-0384
dc.identifier.issn0003-9861
dc.identifier.urihttps://repositorio.ubiobio.cl/handle/123456789/12189
dc.languagespa
dc.publisherARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS
dc.relation.uri10.1016/j.abb.2021.108849
dc.rightsPUBLICADA
dc.titleMECHANISTIC STUDY OF THE BIOSYNTHESIS OF R-PHENYLACETYLCARBINOL BY ACETOHYDROXYACID SYNTHASE ENZYME USING HYBRID QUANTUM MECHANICS/MOLECULAR MECHANICS SIMULATIONS
dc.title.alternativeESTUDIO MECANICISTA DE LA BIOSÍNTESIS DE R-FENILACETILCARBINOL POR LA ENZIMA ACETOHIDROXIÁCIDO SINTASA UTILIZANDO SIMULACIONES HÍBRIDAS DE MECÁNICA CUÁNTICA/MECÁNICA MOLECULAR
dc.typeARTÍCULO
dspace.entity.typePublication
ubb.EstadoPUBLICADA
ubb.Otra ReparticionDEPARTAMENTO DE QUIMICA
ubb.SedeCONCEPCIÓN
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