OXIDATION OF A LIGNIN MODEL-COMPOUND BY THE VERATRYL ALCOHOL CATION-RADICAL - RESULTS FROM MOLECULAR-ORBITAL CALCULATIONS

Veratryl alcohol, a secondary metabolite of Phanerochaete chrysosporiu m and putative mediator of lignin oxidation has been examined using cu rrent techniques in computational chemistry. The proposed oxidative re actions of veratryl alcohol itself and the oxidation of a lignin model compound via electron transfer have been studied. The oxidation of ve ratryl alcohol appears to be controlled by relative endothermicity ass ociated with a proton transfer step within each of the possible oxidat ive pathways. The transfer of an electron from the lignin model compou nd to the veratryl alcohol cation radical is slightly endothermic, occ urring by way of a non-bonded intermediate, with slightly lower energy than either products or reactants.