The electrocatalytic reactions of cysteine and cystine by water-soluble iron porphyrin, manganese porphyrin and iron(II) phenanthrolines

被引:38
作者
Chen, SM
机构
[1] Department of Chemical Engineering, Natl. Taipei Institute of Technology, No. 1, Sect. 3, Chung-Hsiao E. Road
关键词
electrocatalysis; cysteine; cystine; glutathione; porphyrin;
D O I
10.1016/S0013-4686(96)00307-6
中图分类号
O646 [电化学、电解、磁化学];
学科分类号
081704 ;
摘要
The electrocatalytic reduction of L-cystine to L-cysteine and the reduction of the oxidized form of glutathione to the reduced form of glutathione by the (FeTSPP)-T-I species was investigated in aqueous solution. The electrocatalytic oxidations of L-cysteine to L-cystine by FeTSPP, Mn(4-TMPyP), iron(II) tris(3,4,7,8-tetramethyl-1,10-phenanthroline) and iron(II) tris(1,10-phenanthroline) were investigated in aqueous buffer solutions at room temperature. The water-soluble iron tetrakis(4-sulfonatophenyl)porphine (FeTSPP) catalyzed the rapid reduction of L-cystine to L-cysteine after using an electrochemical method to reduce (FeTSPP)-T-III and the iron (III) mu-oxo dimer (TSPP)Fe-III-O-Fe-III(TSPP) to the (FeTSPP)-T-I species. Iron(II) tris(1,10-phenanthroline) and iron(II) tris(3,4,7,8-tetramethyl-1,10-phenanthroline) may perform the electrocatalytic oxidation of L-cysteine to L-cystine. (FeTSPP)-T-III was reduced to (FeTSPP)-T-II by L-cysteine or the reduced form of glutathione. L-cysteine or the reduced form of glutathione were oxidized in a basic solution. If [Fe-III(TSPP)](3-) is oxidized to [Fe-III(TSPP.+)](2-) by electrochemical method, it can oxidize L-cysteine to L-cystine electrocatalytically or oxidize the reduced form of glutathione in strong acidic solutions. If Mn-III(4-TMPyP) is also reduced by L-cysteine to Mn-II(4-TMPyP), L-cysteine oxidizes to L-cystine. The electrocatalytic oxidation of L-cysteine to L-cystine by Mn(4-TMPyP) is performed by two different pathways. Mn-III(4-TMPyP) is oxidized to either Mn-III(4-TMPyP) or Mn-IV(4-TMPyP) by the electrochemical method, then Mn-IV(4-TMPyP) or Mn-III(4-TMPyP) oxidizes L-cysteine to L-cystine. An electrocatalytic oxidation of L-cysteine similar to the oxidation by Mn-IV(4-TMPyP) or Mn-III(4-TMPyP) can also be performed by the reduced form of glutathione. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:1663 / 1673
页数:11
相关论文
共 31 条
[1]   ELECTROCHEMICAL STUDIES OF POLY(MERCAPTOHYDROQUINONE) AND POLY(MERCAPTO-PARA-BENZOQUINONE) FILMS PREPARED BY ELECTROCHEMICAL POLYMERIZATION .6. ELECTROREDUCTION OF L-CYSTINE ON THIOLATES FIXED IN THE POLYMER FILM [J].
ARAI, G ;
SUGAYA, T ;
SAKAMOTO, M ;
YASUMORI, I .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (02) :594-596
[2]   KINETICS AND MECHANISM OF THE REDUCTION OF MANGANESE PORPHYRINS - REACTION AT THE PERIPHERY OF THE PORPHYRIN RING [J].
BALAHURA, RJ ;
KIRBY, RA .
INORGANIC CHEMISTRY, 1994, 33 (06) :1021-1025
[3]   ELECTROCATALYTIC REDUCTION OF NITRITE TO AMMONIA BASED ON A WATER-SOLUBLE IRON PORPHYRIN [J].
BARLEY, MH ;
TAKEUCHI, KJ ;
MEYER, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :5876-5885
[4]  
BERTIMI I, 1994, BIOINORGANIC CHEM
[5]   Bicatalyst electrocatalytic reaction of sulfur oxoanions by water-soluble iron porphyrins and iron(II) tris(1,10-phenanthroline) [J].
Chen, SM .
INORGANICA CHIMICA ACTA, 1996, 244 (02) :155-164
[6]   CHARACTERIZATION OF IRON TETRAKIS(N-METHYL-2-PYRIDYL)PORPHINE IN AQUEOUS-MEDIA - ELECTROCHEMICAL GENERATION OF STABLE IRON(I), IRON(II), IRON(III) AND IRON(IV) PORPHYRINS AT ROOM-TEMPERATURE [J].
CHEN, SM ;
SUN, PJ ;
SU, YO .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1990, 294 (1-2) :151-164
[7]   CHARACTERIZATION OF SINGLY REDUCED IRON(II) PORPHYRINS [J].
DONOHOE, RJ ;
ATAMIAN, M ;
BOCIAN, DF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5593-5599
[8]  
DUNFORD HB, 1982, ADV INORG BIOCHEM, V4, P41
[9]   KINETIC ASPECTS OF THE IRON(III) - TETRAKIS(PARA-SULFONATOPHENYL)PORPHINE SYSTEM [J].
ELAWADY, AA ;
WILKINS, PC ;
WILKINS, RG .
INORGANIC CHEMISTRY, 1985, 24 (13) :2053-2057
[10]   THERMODYNAMIC AND KINETIC PROPERTIES OF AN IRON-PORPHYRIN SYSTEM [J].
FLEISCHER, EB ;
PALMER, JM ;
SRIVASTAVA, TS ;
CHATTERJEE, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (13) :3162-+