Enzymatic and electrochemical oxidation of N-hydroxy compounds -: Redox potential, electron-transfer kinetics, and radical stability

被引:78
作者
Xu, F
Deussen, HJW
Lopez, B
Lam, L
Li, KC
机构
[1] Novozymes Biotech Inc, Davis, CA 95616 USA
[2] Novozymes AS, DK-2760 Malov, Denmark
[3] Oregon State Univ, Dept Forest Prod, Corvallis, OR 97331 USA
来源
EUROPEAN JOURNAL OF BIOCHEMISTRY | 2001年 / 268卷 / 15期
关键词
N-hydroxy; laccase; oxidation; kinetics; stability;
D O I
10.1046/j.1432-1327.2001.02328.x
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A series of N-hydroxyacetanilide and 1-hydroxybenzotriazole analogues derivatized by various functional substituents were studied with regard to redox potential, oxidation by laccase, oxidative stability, and correlation to the electronic and steric properties of the substituents. It was found that substituents carrying conjugative/pi -electron function influenced the redox potential more than substituents carrying inductive/sigma -electron function, and that the electron-transfer from an N-hydroxy moiety to laccase was significantly affected by the redox potential. Electron-withdrawing substituents tended to reduce the electron density on the N-hydroxy group, leading to higher redox potential and lower oxidation rate. Bulky substitution or absence of N-phenyl tended to increase the K-m of the N-hydroxy group, leading to lower oxidation rate. Oxidized N-hydroxy compounds were stabilized by N-phenyl or N-carbonyl group, but not by N-azo or highly strained structure. Potential implication of these effects on laccase-based, N-hydroxy compound-mediated biocatalysis is discussed.
引用
收藏
页码:4169 / 4176
页数:8
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