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Aromatic ring cleavage of a β‐biphenyl ether dimer catalyzed by lignin peroxidase of phanerochaete chrysosporium
Author(s) -
Miki Keiji,
Renganathan V.,
Mayfield Mary B.,
Gold Michael H.
Publication year - 1987
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(87)81337-6
Subject(s) - chemistry , phanerochaete , catalysis , lignin , ring (chemistry) , medicinal chemistry , ether , dimer , hydroxymethyl , dioxolane , biphenyl , lignin peroxidase , peroxidase , substrate (aquarium) , stereochemistry , organic chemistry , enzyme , oceanography , geology
Under aerobic conditions homogeneous lignin peroxidase catalyzed the oxidation of 1‐(4'‐methoxyphenyl)‐2‐(2″,5′‐dimethoxy‐4″‐phenylphenoxy)‐1,3‐dihydroxypropane (I) to yield four products: 1‐(4'‐methoxy‐phenyl)‐1,2,3‐trihydroxypropane (X), 4‐[α‐hydroxy‐α‐(4'‐methoxyphenyl)‐methyl]‐1,3‐dioxolane‐2‐one (V), 4‐(4'‐methoxyphenyl)‐5‐hydroxymethyl‐1,3‐dioxolane‐2‐one (VI) and 5‐hydroxy‐5‐carbomethoxy‐4‐phenyl‐oxol‐3‐en‐2‐one (VIII). V, VI and VIII are all products of ring opening reactions. When the reaction was conducted under anaerobic conditions, the substrate was oxidized but no ring‐cleaved products were detected. During the oxidation of I, 4 atoms of 18 O from 18 O 2 were incorporated into the lactol product VIII.