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Selective dehydrogenation (oxidation) of 3,4‐dimethoxybenzyl alcohol by a non‐heme iron lignin‐peroxidase reaction mimic
Author(s) -
Tung Hui-Chan,
Sawyer Donald T.
Publication year - 1992
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/0014-5793(92)81390-8
Subject(s) - chemistry , dehydrogenation , alcohol , pyridine , lignin , catalysis , reactivity (psychology) , hydrogen peroxide , medicinal chemistry , selectivity , organic chemistry , substrate (aquarium) , lignin peroxidase , peroxidase , enzyme , medicine , oceanography , alternative medicine , pathology , geology
In pyridine, bis(2,2′‐bipyridine)iron(II) (Fe(bpy) 2+ 2 ) activates hydrogen peroxide for the efficient and selective catalytic dehydrogenation (oxidation) of veratryl alcohol (model‐substrate monomer for lignin; 3,4‐(MeO) 2 PhCH 2 OH). Several other complexes (Fe II (OPPh 3 ) 2+ 4 , Fe II (O 2 bpy) 2+ 2 , Fe II (MeCN) 2+ 4 , Fe II (PA) 2 , Fe III Cl 3 ) are effective catalysts for the dehydrogenation of veratryl alcohol and benzyl alcohol, but their selectivity (relative reactivity with 3,4‐(MeO) 2 PhCH 2 OH vs. PhCH 2 OH) is less than the 6.1 ratio that is observed for the optimized Fe II (bpy) 2+ 2 /H 2 O 2 /pyridine(py) system. The reactivities have been determined for several other methoxybenzyl alcohols that are model substrates for lignin (e.g.,4‐MeOPhCH 2 OH and (MeO) 3 PhCH 2 OH).