Comparison of biotransformation mechanisms of 2, 4, 6-trinitrotoluene and its hydride-Meisenheimer metabolite by the old yellow enzyme family of flavoproteins
2,4,6-trinitrotoluene (TNT) is a persistent pollutant; for removing it from environment, the biodegradation becomes an economical and environmentally friendly alternative. However, TNT is difficult to naturally mineralize due to the stability of benzene ring. Interestingly, the hydride metabolite (H...
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| Format: | Article |
| Language: | English |
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KeAi Communications Co. Ltd.
2020-12-01
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| Series: | Energetic Materials Frontiers |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666647220300361 |
| _version_ | 1797936385781399552 |
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| author | Tong Wei Zhilin Yang Mi Zhou DingguoXu Yang Zhou |
| author_facet | Tong Wei Zhilin Yang Mi Zhou DingguoXu Yang Zhou |
| author_sort | Tong Wei |
| collection | DOAJ |
| description | 2,4,6-trinitrotoluene (TNT) is a persistent pollutant; for removing it from environment, the biodegradation becomes an economical and environmentally friendly alternative. However, TNT is difficult to naturally mineralize due to the stability of benzene ring. Interestingly, the hydride metabolite (Hˉ-TNT) of TNT can produce dearomatized products by the biotransformation of old yellow enzyme (OYE) family, which is highly different with TNT. It is a promising strategy for the ring-opening degradation of TNT. Here, we explore the biotransformation difference of TNT and Hˉ-TNT by OYE family. The results show that the electron-withdrawing ability of nitro groups makes them obtain the majority of negative charges of Hˉ-TNT, which promotes the strong interaction between the substrate and key residues. It in turn promotes the formation of π-π stacking configuration between Hˉ-TNT and the flavin mononucleotide (FMN) cofactor, which is a precondition of the aromatic ring reduction. As a result, the aromatic ring reduction occupies an absolute advantage, while the nitro reduction is suppressed. The conclusions are in line with previous understanding and can explain experimental phenomena. This work can provide a valuable reference for the combined strategy of mineralizing TNT. |
| first_indexed | 2024-04-10T18:29:00Z |
| format | Article |
| id | doaj.art-979a7471a2034953913113ec3358cffe |
| institution | Directory Open Access Journal |
| issn | 2666-6472 |
| language | English |
| last_indexed | 2024-04-10T18:29:00Z |
| publishDate | 2020-12-01 |
| publisher | KeAi Communications Co. Ltd. |
| record_format | Article |
| series | Energetic Materials Frontiers |
| spelling | doaj.art-979a7471a2034953913113ec3358cffe2023-02-02T04:50:01ZengKeAi Communications Co. Ltd.Energetic Materials Frontiers2666-64722020-12-0113216226Comparison of biotransformation mechanisms of 2, 4, 6-trinitrotoluene and its hydride-Meisenheimer metabolite by the old yellow enzyme family of flavoproteinsTong Wei0Zhilin Yang1Mi Zhou2 DingguoXu3Yang Zhou4Institute of Chemical Materials, China Academy of Engineering and Physics, Mianyang, 621999, ChinaAutomation Research Institute of China South Industries Group Corporation, Mianyang, 621000, ChinaInstitute of Chemical Materials, China Academy of Engineering and Physics, Mianyang, 621999, ChinaMOE Key Laboratory of Green Chemistry & Technology, College of Chemistry, Sichuan University, Chengdu, Sichuan, 610064, ChinaInstitute of Chemical Materials, China Academy of Engineering and Physics, Mianyang, 621999, China; Corresponding author.2,4,6-trinitrotoluene (TNT) is a persistent pollutant; for removing it from environment, the biodegradation becomes an economical and environmentally friendly alternative. However, TNT is difficult to naturally mineralize due to the stability of benzene ring. Interestingly, the hydride metabolite (Hˉ-TNT) of TNT can produce dearomatized products by the biotransformation of old yellow enzyme (OYE) family, which is highly different with TNT. It is a promising strategy for the ring-opening degradation of TNT. Here, we explore the biotransformation difference of TNT and Hˉ-TNT by OYE family. The results show that the electron-withdrawing ability of nitro groups makes them obtain the majority of negative charges of Hˉ-TNT, which promotes the strong interaction between the substrate and key residues. It in turn promotes the formation of π-π stacking configuration between Hˉ-TNT and the flavin mononucleotide (FMN) cofactor, which is a precondition of the aromatic ring reduction. As a result, the aromatic ring reduction occupies an absolute advantage, while the nitro reduction is suppressed. The conclusions are in line with previous understanding and can explain experimental phenomena. This work can provide a valuable reference for the combined strategy of mineralizing TNT.http://www.sciencedirect.com/science/article/pii/S2666647220300361Biotransformation2,4,6-TrinitrotolueneMeisenheimermetaboliteSimulations |
| spellingShingle | Tong Wei Zhilin Yang Mi Zhou DingguoXu Yang Zhou Comparison of biotransformation mechanisms of 2, 4, 6-trinitrotoluene and its hydride-Meisenheimer metabolite by the old yellow enzyme family of flavoproteins Energetic Materials Frontiers Biotransformation 2,4,6-Trinitrotoluene Meisenheimermetabolite Simulations |
| title | Comparison of biotransformation mechanisms of 2, 4, 6-trinitrotoluene and its hydride-Meisenheimer metabolite by the old yellow enzyme family of flavoproteins |
| title_full | Comparison of biotransformation mechanisms of 2, 4, 6-trinitrotoluene and its hydride-Meisenheimer metabolite by the old yellow enzyme family of flavoproteins |
| title_fullStr | Comparison of biotransformation mechanisms of 2, 4, 6-trinitrotoluene and its hydride-Meisenheimer metabolite by the old yellow enzyme family of flavoproteins |
| title_full_unstemmed | Comparison of biotransformation mechanisms of 2, 4, 6-trinitrotoluene and its hydride-Meisenheimer metabolite by the old yellow enzyme family of flavoproteins |
| title_short | Comparison of biotransformation mechanisms of 2, 4, 6-trinitrotoluene and its hydride-Meisenheimer metabolite by the old yellow enzyme family of flavoproteins |
| title_sort | comparison of biotransformation mechanisms of 2 4 6 trinitrotoluene and its hydride meisenheimer metabolite by the old yellow enzyme family of flavoproteins |
| topic | Biotransformation 2,4,6-Trinitrotoluene Meisenheimermetabolite Simulations |
| url | http://www.sciencedirect.com/science/article/pii/S2666647220300361 |
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