The C-C bond cleavage of a lignin model compound, 1,2-diarylpropane-1,3-diol, with a heme-enzyme model catalyst tetraphenylporphyrinatoiron(III)chloride in the presence of tert-butylhydroperoxide.
The catalytic C-C bond cleavage of a lignin model compound was investigated by use of tetraphenylporphyrinatoiron(III)chloride as a model for enzymic degradation of lignin. The C-C bond of the lignin model compound 1,2-bis(4-ethoxy-3-methoxyphenyl) propane-1,3-diol was oxidatively cleaved by catalysis of iron-porphyrins in the presence of tert-butylhydroperoxide or iodosylbenzene at a room temperature. The products formed after complete oxidation of the substrate were identified as 4-O-ethylvanillin, alpha-hydroxy-4-ethoxy-3-methoxyacetophenone, 4-O-ethylvanillic acid, 4-ethoxy-3-methoxyphenylglycol, 4-ethoxy-3-methoxy-alpha-(4-ethoxy-3-methoxyphenyl)-beta-hydroxypropi ophenone and formaldehyde.
D055598:Chemical Phenomena; D002621:Chemistry; D006418:Heme; D007202:Indicators and Reagents; D008031:Lignin; D008665:Metalloporphyrins; D008961:Models, Structural; D010084:Oxidation-Reduction; D010545:Peroxides; D011409:Propylene Glycols; D020122:tert-Butylhydroperoxide
D007202:Indicators and Reagents; D008665:Metalloporphyrins; D010545:Peroxides; D011409:Propylene Glycols; D006418:Heme; C021175:diaquo(meso-tetraphenylporphinato)iron(III) perchlorate; D008031:Lignin; D020122:tert-Butylhydroperoxide