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J. Biol. Chem., Vol. 275, Issue 21, 15701-15708, May 26, 2000
From the The ability of
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate (HOPDA) hydrolase (BphD) of
Burkholderia cepacia LB400 to hydrolyze polychlorinated
biphenyl (PCB) metabolites was assessed by determining its specificity
for monochlorinated HOPDAs. The relative specificities of BphD for
HOPDAs bearing chlorine substituents on the phenyl moiety were 0.28, 0.38, and 1.1 for 8-Cl, 9-Cl, and 10-Cl HOPDA, respectively,
versus HOPDA (100 mM phosphate, pH 7.5, 25 °C). In contrast, HOPDAs bearing chlorine substituents on the
dienoate moiety were poor substrates for BphD, which hydrolyzed 3-Cl,
4-Cl, and 5-Cl HOPDA at relative maximal rates of 2.1 × 10
Identification of a Serine Hydrolase as a Key Determinant in the
Microbial Degradation of Polychlorinated Biphenyls*
§,§,
,§**
Department of Biochemistry, Pavillon
Marchand, Université Laval,
Quebec City, Quebec G1K 7P4, Canada and the ¶ Department of
Chemistry, Queen's University,
Kingston, Ontario K7L 3N6, Canada
3, 1.4 × 104, and 0.36, respectively, versus HOPDA. The enzymatic transformation of
3-, 5-, 8-, 9-, and 10-Cl HOPDAs yielded stoichiometric quantities of
the corresponding benzoate, indicating that BphD catalyzes the
hydrolysis of these HOPDAs in the same manner as unchlorinated HOPDA.
HOPDAs also underwent a nonenzymatic transformation to products that
included acetophenone. In the case of 4-Cl HOPDA, this transformation
proceeded via the formation of 4-OH HOPDA (t1/2 = 2.8 h; 100 mM phosphate, pH 7.5, 25 °C). 3-Cl HOPDA
(t1/2 = 504 h) was almost 3 times more stable
than 4-OH HOPDA. Finally, 3-Cl, 4-Cl and 4-OH HOPDAs competitively
inhibited the BphD-catalyzed hydrolysis of HOPDA
(Kic values of 0.57 ± 0.04, 3.6 ± 0.2, and 0.95 ± 0.04 µM, respectively). These results
explain the accumulation of HOPDAs and chloroacetophenones in the
microbial degradation of certain PCB congeners. More significantly,
they indicate that in the degradation of PCB mixtures, BphD would be inhibited, thereby slowing the mineralization of all congeners. BphD is
thus a key determinant in the aerobic microbial degradation of PCBs.
*
This research was funded by Strategic Grant STP0193182 from
the Natural Sciences and Engineering Research Council of Canada (to
L. D. E. and V. S.).The costs of publication of this
article were defrayed in part by the
payment of page charges. The article must therefore be hereby marked
"advertisement" in
accordance with 18 U.S.C. Section
1734 solely to indicate this fact.
Current address: Morphochem AG, Gmunder Strasse 37-37a,
81379 Munich, Germany.
**
To whom correspondence should be addressed: Dept. of Microbiology
and Immunology, University of British Columbia, #300, 6174 University
Blvd., Vancouver, British Columbia V6T 1Z3, Canada.
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