Open AccessDioxygenolytic 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
Author(s) -
Engesser Karl H.,
Fietz W.,
Fischer P.,
Schulte P.,
Knackmuss HansJ.
Publication year - 1990
Publication title -
fems microbiology letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.899
H-Index - 151
eISSN - 1574-6968
pISSN - 0378-1097
DOI - 10.1111/j.1574-6968.1990.tb04251.x
Subject(s) - ether , biphenyl , aryl , chemistry , cleavage (geology) , degradation (telecommunications) , bond cleavage , stereochemistry , medicinal chemistry , organic chemistry , catalysis , biology , alkyl , paleontology , telecommunications , fracture (geology) , computer science
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 proto‐catechuate 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.