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Regiospecific oxygenations during ring cleavage of a secondary metabolite, 3,4‐dimethoxybenzyl alcohol catalysed by lignin peroxidase
Author(s) -
Shimada M.,
Hattori T.,
Umezawa T.,
Higuchi T.,
Uzura K.
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)80950-x
Subject(s) - chemistry , cleavage (geology) , lignin , metabolite , peroxidase , ring (chemistry) , alcohol , stereochemistry , organic chemistry , biochemistry , enzyme , biology , fracture (geology) , paleontology
Enzymatic oxidation of veratryl alcohol yielded a new ring cleavage product (δ‐lactone) in addition to the two known γ‐lactone products. The experiment with 18 O‐enriched water and dioxygen clearly showed that one oxygen atom each from water and dioxygen is specifically incorporated into the cleavage product at the original C 3 or C 4 position of 3,4‐dimethoxybenzyl alcohol. A new type of reaction mechanism proposed for the ring cleavage of this compound is rationally explained in good accord with the one‐electron transfer mechanism.