Lignin peroxidase catalysed oxidation of 4-methoxymandelic acid. The role of mediator structure

被引:21
作者
Baciocchi, E [1 ]
Gerini, MF [1 ]
Lanzalunga, O [1 ]
Mancinelli, S [1 ]
机构
[1] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy
关键词
lignin peroxidase; mediation; redox potential; radical cation lifetime;
D O I
10.1016/S0040-4020(02)00997-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A large number of substances have been tested as redox mediators in the UP-catalysed oxidation of 4-methoxymandelic acid (4-MMA) to anisaldehyde. In some cases (i.e. thioanisole), the mediation efficiency is almost equal to the maximum value displayed by the natural mediator veratryl alcohol. The mediation efficiency is a function of the redox potential of the mediator and also appears to depend on the kinetic effectiveness with which the mediator is oxidised by the enzyme. In contrast, the lifetime of the mediator radical cation seems not to play any significant role, which would support the idea that the redox mediation is actually accomplished by a complex between the mediator radical cation and the enzyme. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8087 / 8093
页数:7
相关论文
共 45 条
[1]   The mediation of veratryl alcohol in oxidations promoted by lignin peroxidase: the lifetime of veratryl alcohol radical cation [J].
Baciocchi, E ;
Bietti, M ;
Gerini, MF ;
Lanzalunga, O .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2002, 293 (02) :832-835
[2]  
Baciocchi E, 2001, CHEM-EUR J, V7, P1408, DOI 10.1002/1521-3765(20010401)7:7<1408::AID-CHEM1408>3.0.CO
[3]  
2-M
[4]   CERIC AMMONIUM-NITRATE IN ORGANIC-SYNTHESIS .2. OXIDATION OF N,N-DIMETHYL METHOXYPHENYLMETHYLAMINES TO METHOXYBENZALDEHYDES [J].
BADEA, I ;
COTELLE, P ;
CATTEAU, JP .
SYNTHETIC COMMUNICATIONS, 1994, 24 (14) :2011-2016
[5]   Lifetime, reduction potential and base-induced fragmentation of the veratryl alcohol radical cation in aqueous solution. Pulse radiolysis studies on a ligninase "mediator" [J].
Bietti, M ;
Baciocchi, E ;
Steenken, S .
JOURNAL OF PHYSICAL CHEMISTRY A, 1998, 102 (38) :7337-7342
[6]   LIFETIME AND REACTIVITY OF THE VERATRYL ALCOHOL RADICAL-CATION - IMPLICATIONS FOR LIGNIN PEROXIDASE CATALYSIS [J].
CANDEIAS, LP ;
HARVEY, PJ .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1995, 270 (28) :16745-16748
[7]  
CANDEIAS LP, UNPUB
[8]   Two substrate interaction sites in lignin peroxidase revealed by site-directed mutagenesis [J].
Doyle, WA ;
Blodig, W ;
Veitch, NC ;
Piontek, K ;
Smith, AT .
BIOCHEMISTRY, 1998, 37 (43) :15097-15105
[9]  
Dunford H.B., 1999, HEME PEROXIDASES
[10]  
Eriksson K.-E. L., 1997, BIOTECHNOLOGY PULP P