Biocatalytic oxidation of phenolic compounds by bovine methemoglobin in the presence of H₂O₂: Quantitative structure-activity relationships

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• 作者：M. Teresa Pé ; rez-Prior^a ; ^{MariaTeresa.Perez@uclm.es} ; Rafael Gó ; mez-Bombarelli^b ; ^{R.GomezBombarelli@hw.ac.uk} ; M. Isabel Gonzá ; lez-Sá ; nchez^a ; ^{MIsabel.Gonzalez@uclm.es} ; Edelmira Valero^a ; ^{Edelmira.Valero@uclm.es}
• 关键词：ABTS ; 2 ; 2&rsquo ; -azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) ; 4AP ; 4-amino-phenol ; APAP ; acetaminophen ; BDE ; bond dissociation energy ; 4CNP ; 4-cyanophenol ; 4CP ; 4-chlorophenol ; EA ; electron affinity ; EHOMO ; energy of the highest-occupied molecular
• 刊名：Journal of Hazardous Materials
• 出版年：2012
• 出版时间：30 November, 2012
• 年：2012
• 卷：241-242
• 期：Complete
• 页码：207-215
• 全文大小：660 K

文摘

In the present work, 13 p-substituted phenols with different functional groups have been systematically evaluated as metHb substrates by means of HPLC analysis. Non-hyperbolic kinetics were observed and Hill coefficients in the 0.37-1.00 range were obtained. The catalytic constants and the Hill coefficients were found to be quantitatively correlated with two independent variables: the energy level of the highest-occupied molecular orbital (E_HOMO), which describes the intrinsic redox activity of the substrates and the pK_a-values, which are related to substrate ionization. Oxygen evolution in the presence of each phenol derivative was also measured, and good correlation between peroxidase-like and catalase-like activities of the protein was observed. It is also shown that bovine metHb, although less active than other peroxidases, may represent a good alternative from an economical point of view for phenol removal processes. The equations here obtained may serve as a basis to further explore the potential use of metHb-mediated reactions in the treatment of phenols in wastewaters and to predict which phenol will be removed most efficiently under this treatment with satisfactory reliability.