Dioxygenolytic cleavage of aryl ether bonds: 1,2-dihydro-1,2-dihydroxy-4-carboxybenzophenone as evidence for initial 1,2-dioxygenation in 3- and 4-carboxy biphenyl ether degradation.
A bacterial strain, Pseudomonas sp. POB 310, was enriched with 4-carboxy biphenyl ether as sole source of carbon and energy. Resting cells of POB 310 co-oxidize a substrate analogue, 4-carboxybenzophenone, yielding 1,2-dihydro-1,2-dihydroxy-4-carboxy-benzophenone. The ether bond of 3- and 4-carboxy biphenyl ether is cleaved analogously by initial 1,2-dioxygenation, yielding a hemiacetal which is hydrolysed to protocatechuate and phenol. These intermediates are degraded via an ortho and meta pathway, respectively. Alternative 2,3- and 3,4-dioxygenation can be ruled out as triggering steps in carboxy biphenyl ether degradation.
Engesser
K H
KH
Institut für Mikrobiologie, Universität Stuttgart, F.R.G.
Fietz
W
W
Fischer
P
P
Schulte
P
P
Knackmuss
H J
HJ
D001565:Benzoates / Q000378:metabolism*; D001577:Benzophenones / Q000378:metabolism; D001673:Biodegradation, Environmental; D055598:Chemical Phenomena; D002621:Chemistry; D062385:Hydroxybenzoates / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010647:Phenyl Ethers / Q000378:metabolism*; D011520:Protocatechuate-3,4-Dioxygenase / Q000378:metabolism; D011549:Pseudomonas / Q000254:growth & development / Q000302:isolation & purification / Q000378:metabolism*
D001565:Benzoates; D001577:Benzophenones; D062385:Hydroxybenzoates; D010647:Phenyl Ethers; C065922:1,2-dihydro-1,2-dihydroxy-4-carboxybenzophenone; C065921:4-carboxybiphenyl ether; C009091:protocatechuic acid; D011520:Protocatechuate-3,4-Dioxygenase