3-(2-hydroxyphenyl)catechol as substrate for proximal meta ring cleavage in dibenzofuran degradation by Brevibacterium sp. strain DPO 1361.
Brevibacterium sp. strain DPO 1361 oxygenates dibenzofuran in the unusual angular position. The 3-(2-hydroxyphenyl)catechol thus generated is subject to meta ring cleavage in the proximal position, yielding 2-hydroxy-6-(2-hydroxyphenyl)-6-oxo-2,4-hexadienoic acid, which is hydrolyzed to 2-oxo-4-pentenoate and salicylate by 2-hydroxy-6-oxo-6-phenyl-2,4-hexadienoic acid hydrolase. The proximal mode of ring cleavage is definitely established by isolation and unequivocal structural characterization of a cyclization product of 2-hydroxy-6-(2-hydroxyphenyl)-6-oxo-2,4-hexadienoic acid, i.e., 3-(chroman-4-on-2-yl)pyruvate.
Strubel
V
V
Institut für Mikrobiologie, Universität Stuttgart, Federal Republic of Germany.
Engesser
K H
KH
Fischer
P
P
Knackmuss
H J
HJ
D001572:Benzofurans / Q000378:metabolism*; D001951:Brevibacterium / Q000378:metabolism*; D002396:Catechols / Q000378:metabolism*; D002852:Chromatography, Ion Exchange; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy
D001572:Benzofurans; D002396:Catechols; C023614:dibenzofuran; C067814:3-(2-hydroxyphenyl)catechol