3-氯儿茶酚通过双加氧酶进行远端裂解生成3-氯-2-羟基粘康酸半醛。
Distal cleavage of 3-chlorocatechol by an extradiol dioxygenase to 3-chloro-2-hydroxymuconic semialdehyde.
作者信息
Riegert U, Heiss G, Fischer P, Stolz A
机构信息
Institut für Mikrobiologie, Universität Stuttgart, 70569 Stuttgart, Germany.
出版信息
J Bacteriol. 1998 Jun;180(11):2849-53. doi: 10.1128/JB.180.11.2849-2853.1998.
Abstract
A 2,3-dihydroxybiphenyl 1,2-dioxygenase from the naphthalenesulfonate-degrading bacterium Sphingomonas sp. strain BN6 oxidized 3-chlorocatechol to a yellow product with a strongly pH-dependent absorption maximum at 378 nm. A titration curve suggested (de)protonation of an ionizable group with a pKa of 4.4. The product was isolated, purified, and converted, by treatment with diazomethane, to a dimethyl derivative and, by incubation with ammonium chloride, to a picolinic acid derivative. Mass spectra and 1H and 13C nuclear magnetic resonance (NMR) data for these two derivatives prove a 3-chloro-2-hydroxymuconic semialdehyde structure for the metabolite, resulting from distal (1,6) cleavage of 3-chlorocatechol. 3-Methylcatechol and 2,3-dihydroxybiphenyl are oxidized by this enzyme, in contrast, via proximal (2,3) cleavage.
摘要
来自萘磺酸盐降解细菌鞘氨醇单胞菌属菌株BN6的2,3-二羟基联苯1,2-双加氧酶将3-氯儿茶酚氧化为一种黄色产物，该产物在378 nm处有强烈的pH依赖性吸收最大值。滴定曲线表明存在一个pKa为4.4的可电离基团的（去）质子化。该产物经分离、纯化后，用重氮甲烷处理转化为二甲基衍生物，与氯化铵孵育转化为吡啶甲酸衍生物。这两种衍生物的质谱以及1H和13C核磁共振（NMR）数据证明该代谢产物为3-氯-2-羟基粘康酸半醛结构，是由3-氯儿茶酚的远端（1,6）裂解产生的。相比之下，3-甲基儿茶酚和2,3-二羟基联苯经该酶氧化是通过近端（2,3）裂解。
相似文献
1
Distal cleavage of 3-chlorocatechol by an extradiol dioxygenase to 3-chloro-2-hydroxymuconic semialdehyde.3-氯儿茶酚通过双加氧酶进行远端裂解生成3-氯-2-羟基粘康酸半醛。
J Bacteriol. 1998 Jun;180(11):2849-53. doi: 10.1128/JB.180.11.2849-2853.1998.
2
Catalytic properties of the 3-chlorocatechol-oxidizing 2, 3-dihydroxybiphenyl 1,2-dioxygenase from Sphingomonas sp. strain BN6.鞘氨醇单胞菌属菌株BN6中3-氯儿茶酚氧化型2,3-二羟基联苯1,2-双加氧酶的催化特性
J Bacteriol. 1999 Aug;181(16):4812-7. doi: 10.1128/JB.181.16.4812-4817.1999.
3
Characterization of a 2,3-dihydroxybiphenyl dioxygenase from the naphthalenesulfonate-degrading bacterium strain BN6.萘磺酸盐降解菌菌株BN6中2,3-二羟基联苯双加氧酶的特性分析
J Bacteriol. 1995 Oct;177(20):5865-71. doi: 10.1128/jb.177.20.5865-5871.1995.
4
Altering catalytic properties of 3-chlorocatechol-oxidizing extradiol dioxygenase from Sphingomonas xenophaga BN6 by random mutagenesis.通过随机诱变改变食异源鞘氨醇单胞菌BN6中3-氯儿茶酚氧化外二醇双加氧酶的催化特性。
J Bacteriol. 2001 Apr;183(7):2322-30. doi: 10.1128/JB.183.7.2322-2330.2001.
5
Characterization of a novel thermostable Mn(II)-dependent 2,3-dihydroxybiphenyl 1,2-dioxygenase from a polychlorinated biphenyl- and naphthalene-degrading Bacillus sp. JF8.从一株多氯联苯和萘降解芽孢杆菌JF8中鉴定一种新型热稳定的依赖锰（II）的2,3-二羟基联苯1,2-双加氧酶
J Biol Chem. 2003 Jun 13;278(24):21483-92. doi: 10.1074/jbc.M210240200. Epub 2003 Apr 2.
6
Metabolism of 4-chlorophenol by Azotobacter sp. GP1: structure of the meta cleavage product of 4-chlorocatechol.固氮菌属GP1对4-氯苯酚的代谢：4-氯邻苯二酚间位裂解产物的结构
FEMS Microbiol Lett. 1994 Feb 1;116(1):73-8. doi: 10.1111/j.1574-6968.1994.tb06678.x.
7
A new modified ortho cleavage pathway of 3-chlorocatechol degradation by Rhodococcus opacus 1CP: genetic and biochemical evidence.食油假单胞菌1CP对3-氯儿茶酚降解的一种新的改良邻位裂解途径：遗传学和生物化学证据
J Bacteriol. 2002 Oct;184(19):5282-92. doi: 10.1128/JB.184.19.5282-5292.2002.
8
Analysis of a new dimeric extradiol dioxygenase from a naphthalenesulfonate-degrading sphingomonad.对一种来自萘磺酸盐降解鞘氨醇单胞菌的新型二聚体外二醇双加氧酶的分析。
Microbiology (Reading). 1997 May;143 ( Pt 5):1691-1699. doi: 10.1099/00221287-143-5-1691.
9
Conversion of 3-chlorocatechol by various catechol 2,3-dioxygenases and sequence analysis of the chlorocatechol dioxygenase region of Pseudomonas putida GJ31.恶臭假单胞菌GJ31中各种儿茶酚2,3-双加氧酶对3-氯儿茶酚的转化及氯儿茶酚双加氧酶区域的序列分析
J Bacteriol. 1999 Feb;181(4):1309-18. doi: 10.1128/JB.181.4.1309-1318.1999.
10
Identification of an extradiol dioxygenase involved in tetralin biodegradation: gene sequence analysis and purification and characterization of the gene product.参与四氢萘生物降解的双加氧酶的鉴定：基因序列分析以及基因产物的纯化与特性研究
J Bacteriol. 2000 Feb;182(3):789-95. doi: 10.1128/JB.182.3.789-795.2000.
引用本文的文献
1
Plasmid Backbone Impacts Conjugation Rate, Transconjugant Fitness, and Community Assembly of Genetically Bioaugmented Soil Microbes for PAH Bioremediation.质粒骨架影响用于多环芳烃生物修复的基因增强型土壤微生物的接合率、接合子适应性及群落组装。
ACS Environ Au. 2025 Jan 22;5(2):241-252. doi: 10.1021/acsenvironau.4c00123. eCollection 2025 Mar 19.
2
Bioconversion of 4-hydroxyestradiol by extradiol ring-cleavage dioxygenases from Novosphingobium sp. PP1Y.新型鞘氨醇单胞菌 PP1Y 中外切二醇环裂解双加氧酶对 4-羟基雌二醇的生物转化。
Sci Rep. 2023 Feb 1;13(1):1835. doi: 10.1038/s41598-023-28908-2.
3
Biodegradation of 7-Hydroxycoumarin in 7HK4 via -Hydroxylation of 3-(2,4-Dihydroxyphenyl)-propionic Acid.3-(2,4-二羟基苯基）-丙酸通过β-羟化作用对 7-羟基香豆素的生物降解作用研究。
Molecules. 2018 Oct 12;23(10):2613. doi: 10.3390/molecules23102613.
4
Degradation of toluene by ortho cleavage enzymes in Burkholderia fungorum FLU100.伯克霍尔德氏菌FLU100中邻位裂解酶对甲苯的降解作用
Microb Biotechnol. 2015 Jan;8(1):143-54. doi: 10.1111/1751-7915.12147. Epub 2014 Aug 18.
5
Degradation of 2,3-dihydroxybenzoate by a novel meta-cleavage pathway.通过一条新的间位裂解途径降解2,3-二羟基苯甲酸酯。
J Bacteriol. 2012 Aug;194(15):3851-60. doi: 10.1128/JB.00430-12. Epub 2012 May 18.
6
Substrate specificity and expression of three 2,3-dihydroxybiphenyl 1,2-dioxygenases from Rhodococcus globerulus strain P6.球形红球菌P6菌株中三种2,3-二羟基联苯1,2-双加氧酶的底物特异性及表达
J Bacteriol. 2003 May;185(9):2944-51. doi: 10.1128/JB.185.9.2944-2951.2003.
7
Differential expression of two catechol 1,2-dioxygenases in Burkholderia sp. strain TH2.伯克霍尔德氏菌属TH2菌株中两种儿茶酚1,2-双加氧酶的差异表达
J Bacteriol. 2002 Oct;184(20):5714-22. doi: 10.1128/JB.184.20.5714-5722.2002.
8
Altering catalytic properties of 3-chlorocatechol-oxidizing extradiol dioxygenase from Sphingomonas xenophaga BN6 by random mutagenesis.通过随机诱变改变食异源鞘氨醇单胞菌BN6中3-氯儿茶酚氧化外二醇双加氧酶的催化特性。
J Bacteriol. 2001 Apr;183(7):2322-30. doi: 10.1128/JB.183.7.2322-2330.2001.
9
Bioaugmentation of activated sludge by an indigenous 3-chloroaniline-degrading Comamonas testosteroni strain, I2gfp.用本地的3-氯苯胺降解睾丸酮丛毛单胞菌菌株I2gfp对活性污泥进行生物强化。
Appl Environ Microbiol. 2000 Jul;66(7):2906-13. doi: 10.1128/AEM.66.7.2906-2913.2000.
10
Identification of an extradiol dioxygenase involved in tetralin biodegradation: gene sequence analysis and purification and characterization of the gene product.参与四氢萘生物降解的双加氧酶的鉴定：基因序列分析以及基因产物的纯化与特性研究
J Bacteriol. 2000 Feb;182(3):789-95. doi: 10.1128/JB.182.3.789-795.2000.
本文引用的文献
1
Biodegradation of 2,4-Dichlorophenol through a Distal meta-Fission Pathway.通过末端 meta 断裂途径对 2,4-二氯苯酚的生物降解。
Appl Environ Microbiol. 1997 May;63(5):2054-7. doi: 10.1128/aem.63.5.2054-2057.1997.
2
Formation of Dimethylmuconolactones from Dimethylphenols by Alcaligenes eutrophus JMP 134.阿氏假单胞菌 JMP134 由二甲基苯酚生成二甲基巴豆基内酯。
Appl Environ Microbiol. 1995 Jun;61(6):2159-65. doi: 10.1128/aem.61.6.2159-2165.1995.
3
Suicide Inactivation of Catechol 2,3-Dioxygenase from Pseudomonas putida mt-2 by 3-Halocatechols.假单胞菌 mt-2 儿茶酚 2,3-双加氧酶的自杀失活作用 3-卤代儿茶酚。
Appl Environ Microbiol. 1984 Mar;47(3):500-5. doi: 10.1128/aem.47.3.500-505.1984.
4
Degradation of chloroaromatics: purification and characterization of a novel type of chlorocatechol 2,3-dioxygenase of Pseudomonas putida GJ31.氯代芳烃的降解：恶臭假单胞菌GJ31新型氯儿茶酚2,3-双加氧酶的纯化与特性分析
J Bacteriol. 1998 Jan;180(2):296-302. doi: 10.1128/JB.180.2.296-302.1998.
5
Microbial degradation of chloroaromatics: use of the meta-cleavage pathway for mineralization of chlorobenzene.氯代芳烃的微生物降解：利用间位裂解途径实现氯苯的矿化
J Bacteriol. 1997 Jul;179(14):4530-7. doi: 10.1128/jb.179.14.4530-4537.1997.
6
Analysis of a new dimeric extradiol dioxygenase from a naphthalenesulfonate-degrading sphingomonad.对一种来自萘磺酸盐降解鞘氨醇单胞菌的新型二聚体外二醇双加氧酶的分析。
Microbiology (Reading). 1997 May;143 ( Pt 5):1691-1699. doi: 10.1099/00221287-143-5-1691.
7
Three-dimensional structures of free form and two substrate complexes of an extradiol ring-cleavage type dioxygenase, the BphC enzyme from Pseudomonas sp. strain KKS102.来自假单胞菌属菌株KKS102的双加氧酶BphC（一种间位二醇裂解型双加氧酶）的游离形式以及两种底物复合物的三维结构。
J Mol Biol. 1996 Feb 9;255(5):735-52. doi: 10.1006/jmbi.1996.0060.
8
Metabolism of 4-chlorophenol by Azotobacter sp. GP1: structure of the meta cleavage product of 4-chlorocatechol.固氮菌属GP1对4-氯苯酚的代谢：4-氯邻苯二酚间位裂解产物的结构
FEMS Microbiol Lett. 1994 Feb 1;116(1):73-8. doi: 10.1111/j.1574-6968.1994.tb06678.x.
9
Regulation of chloro- and methylphenol degradation in Comamonas testosteroni JH5.睾丸酮丛毛单胞菌JH5中氯酚和甲基酚降解的调控
Appl Environ Microbiol. 1994 Jul;60(7):2330-8. doi: 10.1128/aem.60.7.2330-2338.1994.
10
Identification of functional residues in a 2-hydroxymuconic semialdehyde hydrolase. A new member of the alpha/beta hydrolase-fold family of enzymes which cleaves carbon-carbon bonds.
J Biol Chem. 1995 Mar 17;270(11):6403-411. doi: 10.1074/jbc.270.11.6403.
Zotero 插件