EVIDENCE FOR A NOVEL PATHWAY IN THE DEGRADATION OF FLUORENE BY PSEUDOMONAS SP STRAIN F274

被引:91
作者
GRIFOLL, M
SELIFONOV, SA
CHAPMAN, PJ
机构
[1] UNIV W FLORIDA,CTR ENVIRONM DIAGNOST & BIOREMEDIAT,PENSACOLA,FL 32514
[2] US EPA,ENVIRONM RES LAB,GULF BREEZE,FL 32561
关键词
D O I
10.1128/AEM.60.7.2438-2449.1994
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
A fluorene-utilizing microorganism, identified as a species of Pseudomonas, was isolated from soil severely contaminated from creosote use and was shown to accumulate six major metabolites from fluorene in washed-cell incubations. Five of these products were identified as 9-fluorenol, 9-fluorenone, (+)-1,1a-dihydroxy-1-hydro-9-fluorenone, 8-hydroxy-3,4-benzocoumarin, and phthalic acid. This last compound was also identified in growing cultures supported by fluorene. Fluorene assimilation into cell biomass was estimated to be approximately 50%. The structures of accumulated products indicate that a previously undescribed pathway of fluorene catabolism is employed by Pseudomonas sp. strain F274. This pathway involves oxygenation of fluorene at C-9 to give 9-fluorenol, which is then dehydrogenated to the corresponding ketone, 9-fluorenone. Dioxygenase attack on 9-fluorenone adjacent to the carbonyl group gives an angular diol, 1,1a-dihydroxy-1-hydro-9-fluorenone. Identification of 8-hydroxy-3,4-benzocoumarin and phthalic acid suggests that the five-membered ring of the angular diol is opened first and that the resulting 2'-carboxy derivative of 2,3-dihydroxy-biphenyl is catabolized by reactions analogous to those of biphenyl degradation, leading to the formation of phthalic acid. Cell extracts of fluorene-grown cells possessed high levels of an enzyme characteristic of phthalate catabolism, 4,5-dihydroxyphthalate decarboxylase, together with protocatechuate 4,5-dioxygenase. On the basis of these findings, a pathway of fluorene degradation is proposed to account for its conversion to intermediary metabolites. A range of compounds with structures similar to that of fluorene was acted on by fluorene-grown cells to give products consistent with the initial reactions proposed.
引用
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页码:2438 / 2449
页数:12
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共 44 条
  • [1] [Anonymous], 1990, PHYSL BACTERIAL CELL
  • [2] BLACK TH, 1983, ALDRICHIM ACTA, V16, P39
  • [3] BOYD DR, 1991, TETRAHEDRON LETT, V32, P3887
  • [4] BOYD DR, 1989, J CHEM SOC CHEM COMM, V6, P339
  • [5] STEREOSPECIFIC HYDROXYLATION OF INDAN BY ESCHERICHIA-COLI CONTAINING THE CLONED TOLUENE DIOXYGENASE GENES FROM PSEUDOMONAS-PUTIDA F1
    BRAND, JM
    CRUDEN, DL
    ZYLSTRA, GJ
    GIBSON, DT
    [J]. APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 1992, 58 (10) : 3407 - 3409
  • [6] BUNZ PV, 1993, J BACTERIOL, V175, P6467
  • [7] Cerniglia Carl E., 1992, Biodegradation, V3, P351, DOI 10.1007/BF00129093
  • [8] CHAPMAN PJ, FOSSIL FUEL BIODEGRA
  • [9] CATABOLISM OF PROTOCATECHUATE BY BACILLUS-MACERANS
    CRAWFORD, RL
    BROMLEY, JW
    PERKINSOLSON, PE
    [J]. APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 1979, 37 (03) : 614 - 618
  • [10] STERIC ACCELERATION OF LACTONIZATION REACTIONS - ANALYSIS OF STEREOPOPULATION-CONTROL
    DANFORTH, C
    NICHOLSON, AW
    JAMES, JC
    LOUDON, GM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (14) : 4275 - 4281