DEGRADATION OF 2,4-DINITROTOLUENE BY THE LIGNIN-DEGRADING FUNGUS PHANEROCHAETE-CHRYSOSPORIUM

被引:142
作者
VALLI, K [1 ]
BROCK, BJ [1 ]
JOSHI, DK [1 ]
GOLD, MH [1 ]
机构
[1] OREGON GRAD INST SCI & TECHNOL, DEPT CHEM & BIOL SCI, 19600 NW VON NEUMANN DR, BEAVERTON, OR 97006 USA
关键词
D O I
10.1128/AEM.58.1.221-228.1992
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
Under ligninolytic conditions, the white rot basidiomycete Phanerochaete chrysosporium mineralizes 2,4-dinitrotoluene (I). The pathway for the degradation of I was elucidated by the characterization of fungal metabolites and oxidation products generated by lignin peroxidase (LiP), manganese peroxidase (MnP), and crude intracellular cell extracts. The multistep pathway involves the initial reduction of I to yield 2-amino-4-nitrotoluene (II). II is oxidized by MnP to yield 4-nitro-1,2-benzoquinone (XII) and methanol. XII is then reduced to 4-nitro-1,2-hydroquinone (V), and the latter is methylated to 1,2-dimethoxy-4-nitrobenzene (X). 4-Nitro-1,2-hydroquinone (V) is also oxidized by MnP to yield nitrite and 2-hydroxybenzoquinone, which is reduced to form 1,2,4-trihydroxybenzene (VII). 1,2-Dimethoxy-4-nitrobenzene (X) is oxidized by LiP to yield nitrite, methanol, and 2-methoxy-1,4-benzoquinone (VI), which is reduced to form 2-methoxy-1,4-hydroquinone (IX). The latter is oxidized by LiP and MnP to 4-hydroxy-1,2-benzoquinone, which is reduced to 1,2,4-trihydroxybenzene (VII). The kev intermediate 1,2,4-trihydroxybenzene is ring cleaved by intracellular cell extracts to produce, after reduction, beta-ketoadipic acid. In this pathway, initial reduction of a nitroaromatic group generates the peroxidase substrate 11. Oxidation of II releases methanol and generates 4-nitro-1,2-benzoquinone (XII), which is recycled by reduction and methylation reactions to regenerate intermediates which are in turn substrates for peroxidase-catalyzed oxidation leading to removal of the second nitro group. Thus, this unique pathway apparently results in the removal of both aromatic nitro groups before ring cleavage takes place.
引用
收藏
页码:221 / 228
页数:8
相关论文
共 50 条
  • [21] DEGRADATION OF BENZENE, TOLUENE, ETHYLBENZENE, AND XYLENES (BTEX) BY THE LIGNIN-DEGRADING BASIDIOMYCETE PHANEROCHAETE-CHRYSOSPORIUM
    YADAV, JS
    REDDY, CA
    APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 1993, 59 (03) : 756 - 762
  • [22] COMPARISON OF 2 LIGNIN-DEGRADING FUNGI - PHLEBIA-RADIATA AND PHANEROCHAETE-CHRYSOSPORIUM
    KANTELINEN, A
    WALDNER, R
    NIKUPAAVOLA, ML
    LEISOLA, MSA
    APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 1988, 28 (02) : 193 - 198
  • [23] NITROGEN-DEREGULATED-MUTANTS OF PHANEROCHAETE-CHRYSOSPORIUM - A LIGNIN-DEGRADING BASIDIOMYCETE
    BOOMINATHAN, K
    DASS, SB
    RANDALL, TA
    REDDY, CA
    ARCHIVES OF MICROBIOLOGY, 1990, 153 (06) : 521 - 527
  • [24] MATING SYSTEM AND BASIDIOSPORE FORMATION IN THE LIGNIN-DEGRADING BASIDIOMYCETE PHANEROCHAETE-CHRYSOSPORIUM
    ALIC, M
    LETZRING, C
    GOLD, MH
    APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 1987, 53 (07) : 1464 - 1469
  • [25] ISOLATION AND TRANSFORMATION OF URACIL AUXOTROPHS OF THE LIGNIN-DEGRADING BASIDIOMYCETE PHANEROCHAETE-CHRYSOSPORIUM
    AKILESWARAN, L
    ALIC, M
    CLARK, EK
    HORNICK, JL
    GOLD, MH
    CURRENT GENETICS, 1993, 23 (04) : 351 - 356
  • [26] TRANSFORMATION BY COMPLEMENTATION OF AN ADENINE AUXOTROPH OF THE LIGNIN-DEGRADING BASIDIOMYCETE PHANEROCHAETE-CHRYSOSPORIUM
    ALIC, M
    KORNEGAY, JR
    PRIBNOW, D
    GOLD, MH
    APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 1989, 55 (02) : 406 - 411
  • [27] DEGRADATION OF LIGNIN BY PHANEROCHAETE-CHRYSOSPORIUM
    SCHOEMAKER, HE
    LEISOLA, MSA
    JOURNAL OF BIOTECHNOLOGY, 1990, 13 (2-3) : 101 - 109
  • [28] OXIDATION REDUCTION POTENTIALS AND IONIZATION STATES OF EXTRACELLULAR PEROXIDASES FROM THE LIGNIN-DEGRADING FUNGUS PHANEROCHAETE-CHRYSOSPORIUM
    MILLIS, CD
    CAI, DY
    STANKOVICH, MT
    TIEN, M
    BIOCHEMISTRY, 1989, 28 (21) : 8484 - 8489
  • [29] LIGNIN DEGRADATION BY PHANEROCHAETE-CHRYSOSPORIUM
    KIRK, TK
    ISI ATLAS OF SCIENCE-BIOCHEMISTRY, 1988, 1 (01): : 71 - 76
  • [30] CLONING AND SEQUENCING OF A LIGNINASE GENE FROM A LIGNIN-DEGRADING BASIDIOMYCETE, PHANEROCHAETE-CHRYSOSPORIUM
    ASADA, Y
    KIMURA, Y
    KUWAHARA, M
    TSUKAMOTO, A
    KOIDE, K
    OKA, A
    TAKANAMI, M
    APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 1988, 29 (05) : 469 - 473