TRANSFORMATIONS OF AROMATIC-COMPOUNDS BY NITROSOMONAS-EUROPAEA

被引:172
作者
KEENER, WK [1 ]
ARP, DJ [1 ]
机构
[1] OREGON STATE UNIV,NITROGEN FIXAT RES LAB,CORVALLIS,OR 97331
关键词
D O I
10.1128/AEM.60.6.1914-1920.1994
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
Benzene and a variety of substituted benzenes inhibited ammonia oxidation by intact cells of Nitrosomonas europaea. In most cases, the inhibition was accompanied by transformation of the aromatic compound to a more oxidized product or products. All products detected were aromatic, and substituents were often oxidized but were not separated from the benzene ring. Most transformations were enhanced by (NH4)(2)SO4 (12.5 mM) and were prevented by C2H2, a mechanism-based inactivator of ammonia monooxygenase (AMO). AMO catalyzed alkyl substituent hydroxylations, styrene epoxidation, ethylbenzene desaturation to styrene, and aniline oxidation to nitrobenzene (and unidentified products). Alkyl substituents were preferred oxidation sites, but the ring was also oxidized to produce phenolic compounds from benzene, ethylbenzene, halobenzenes, phenol, and nitrobenzene. No carboxylic acids were identified. Ethylbenzene was oxidized via styrene to two products common also to oxidation of styrene; production of styrene is suggestive of an electron transfer mechanism for AMO. Iodobenzene and 1,2-dichlorobenzene were oxidized slowly to halophenols; 1,4-dichlorobenzene was not transformed. No 2-halophenols were detected as products. Several hydroxymethyl (-CH2OH)-substituted aromatics and p-cresol were oxidized by C2H2-treated cells to the corresponding aldehydes, benzaldehyde was reduced to benzyl alcohol, and o-cresol and 2,5-dimethylphenol were not depleted.
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页码:1914 / 1920
页数:7
相关论文
共 32 条
[31]   MECHANISTIC STUDIES ON DOPAMINE BETA-MONOOXYGENASE CATALYSIS - N-DEALKYLATION AND MECHANISM-BASED INHIBITION BY BENZYLIC-NITROGEN-CONTAINING COMPOUNDS - EVIDENCE FOR A SINGLE-ELECTRON-TRANSFER MECHANISM [J].
WIMALASENA, K ;
MAY, SW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (13) :4036-4046
[32]  
WOOD PM, 1986, NITRIFICATION, P39