Abstract
A Structure Activity Relationship (SAR) study for laccase mediator systems was performed in order to correctly classify different natural phenolic mediators. Decision tree (DT) classification models with a set of five quantum-chemical calculated molecular descriptors were used. These descriptors included redox potential (ɛ°), ionization energy (E(i)), pK(a), enthalpy of formation of radical (Δ(f)H), and OH bond dissociation energy (D(O-H)). The rationale for selecting these descriptors is derived from the laccase-mediator mechanism. To validate the DT predictions, the kinetic constants of different compounds as laccase substrates, their ability for pesticide transformation as laccase-mediators, and radical stability were experimentally determined using Coriolopsis gallica laccase and the pesticide dichlorophen. The prediction capability of the DT model based on three proposed descriptors showed a complete agreement with the obtained experimental results.
Copyright © 2012 Elsevier Inc. All rights reserved.
Publication types
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Comparative Study
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Research Support, Non-U.S. Gov't
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Validation Study
MeSH terms
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Acetophenones / chemistry
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Acetophenones / pharmacology
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Benzaldehydes / chemistry
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Benzaldehydes / pharmacology
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Biocatalysis / drug effects*
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Catechols / chemistry
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Catechols / pharmacology
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Coumaric Acids / chemistry
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Coumaric Acids / pharmacology
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Decision Trees
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Dichlorophen / chemistry
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Dichlorophen / pharmacology
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Fungal Proteins / chemistry
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Fungal Proteins / metabolism
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Hydrazones / chemistry
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Hydrazones / pharmacology
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Laccase / chemistry
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Laccase / metabolism*
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Models, Chemical
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Models, Molecular
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Molecular Structure
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Nitrophenols / chemistry
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Nitrophenols / pharmacology
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Oxidation-Reduction
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Phenols / chemistry
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Phenols / pharmacology
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Polyporales / enzymology
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Protein Conformation
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Quantitative Structure-Activity Relationship
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Vanillic Acid / chemistry
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Vanillic Acid / pharmacology
Substances
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Acetophenones
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Benzaldehydes
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Catechols
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Coumaric Acids
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Fungal Proteins
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Hydrazones
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Nitrophenols
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Phenols
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syringaldazine
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syringaldehyde
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2,6-dichloro-4-nitrophenol
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sinapinic acid
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acetosyringone
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guaethol
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Laccase
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Vanillic Acid
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3-methoxycatechol
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Dichlorophen