Formation of N-acetylaminophenol from anthranilic acid by Pseudomonas pyrrocinia ATCC15958

Lübbe, C

doi:10.1016/0378-1097(82)90153-7

Cited by 2 publications

(5 citation statements)

References 8 publications

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“…Our results may also predict that AAP is generated from 2-aminophenols by the acetylation of NATs, which is similar with the function of arylamine N-acetyltransferase in Streptomyces griseus [23]. In addition, it is worth mentioning that Lübbe et al [16] suggested that anthranilic acid may be one intermediate to generate AAP. In consideration of the similar structure of anthranilic acid Fig.…”

Section: Identification Of Genes Involved In Aap Biosynthesissupporting

confidence: 81%

“…In conclusion, the structure of this compound was confirmed to be 2-acetamidophenol. Although natural 2-acetamidophenol has been reported in the strains P. pyrrocinia ATCC 15958 [16], P. fluorescens 2-79 [9], Fusarium verticillioides [17], co-culture strains Actinokineospora sp. EG49 and Nocardiopsis sp.…”

Section: Purification and Structural Elucidation Of The New Metabolitementioning

confidence: 99%

“…Natural AAP production was first reported in the liquid culture of strain Pseudomonas fluorescens 2-79, but the maximum titer of AAP was only 50 mg/L [9], that is too low to meet the current demand for industrial production. AAP was subsequently found in various strains, including P. pyrrocinia ATCC 15,958 [16], Fusarium verticillioides [17], co-culture strains Actinokineospora sp. EG49 and Nocardiopsis sp.…”

Section: Introductionmentioning

confidence: 99%

“…Lehninger et al reported that AAP is derived from tyrosine and phenylalanine through the tyrosine biosynthesis pathway [20]. Lübbe et al reported that AAP is converted from anthranilic acid [16]. Winkler et al suggested that AAP arises from chorismic acid via amino-deoxyisochorismic acid (ADIC) and 3-hydroxyanthranilic acid (HAA) [21].…”

Section: Introductionmentioning

confidence: 99%

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Identification of new arylamine N-acetyltransferases and enhancing 2-acetamidophenol production in Pseudomonas chlororaphis HT66

Guo

Wang

et al. 2020

Microb Cell Fact

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Background: 2-Acetamidophenol (AAP) is an aromatic compound with the potential for antifungal, anti-inflammatory, antitumor, anti-platelet, and anti-arthritic activities. Due to the biosynthesis of AAP is not yet fully understood, AAP is mainly produced by chemical synthesis. Currently, metabolic engineering of natural microbial pathway to produce valuable aromatic compound has remarkable advantages and exhibits attractive potential. Thus, it is of paramount importance to develop a dominant strain to produce AAP by elucidating the AAP biosynthesis pathway. Result: In this study, the active aromatic compound AAP was first purified and identified in gene phzB disruption strain HT66ΔphzB, which was derived from Pseudomonas chlororaphis HT66. The titer of AAP in the strain HT66ΔphzB was 236.89 mg/L. Then, the genes involved in AAP biosynthesis were determined. Through the deletion of genes phzF, Nat and trpE, AAP was confirmed to have the same biosynthesis route as phenazine-1-carboxylic (PCA). Moreover, a new arylamine N-acetyltransferases (NATs) was identified and proved to be the key enzyme required for generating AAP by in vitro assay. P. chlororaphis P3, a chemical mutagenesis mutant strain of HT66, has been demonstrated to have a robust ability to produce antimicrobial phenazines. Therefore, genetic engineering, precursor addition, and culture optimization strategies were used to enhance AAP production in P. chlororaphis P3. The inactivation of phzB in P3 increased AAP production by 92.4%. Disrupting the phenazine negative regulatory genes lon and rsmE and blocking the competitive pathway gene pykA in P3 increased AAP production 2.08-fold, which also confirmed that AAP has the same biosynthesis route as PCA. Furthermore, adding 2-amidophenol to the KB medium increased AAP production by 64.6%, which suggested that 2-amidophenol is the precursor of AAP. Finally, by adding 5 mM 2-amidophenol and 2 mM Fe 3+ to the KB medium, the production of AAP reached 1209.58 mg/L in the engineered strain P3ΔphzBΔlonΔpykAΔrsmE using a shaking-flask culture. This is the highest microbial-based AAP production achieved to date. Conclusion: In conclusion, this study clarified the biosynthesis process of AAP in Pseudomonas and provided a promising host for industrial-scale biosynthesis of AAP from renewable resources.

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Section: Identification Of Genes Involved In Aap Biosynthesissupporting

confidence: 81%

Section: Purification and Structural Elucidation Of The New Metabolitementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Identification of new arylamine N-acetyltransferases and enhancing 2-acetamidophenol production in Pseudomonas chlororaphis HT66

Guo

Wang

et al. 2020

Microb Cell Fact

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“…18 In normal conditions, the biosynthesis of chemical products needs the corresponding biosynthetic pathways and enzymes; however, until recently, the key step in the AAP synthesis was still a mystery. AAP production is derived from shikimic acid pathway or detoxification of 2benzoxazolinone, such as it is transformed from 2-acetylanthranilic acid, 19 or 3-hydroxyanthranilic acid, 9,20 or hydrolysis and acetylation of 2-benzoxazolinone 7 (Figure S3), but some details need further clarification. So far, only two AAP production related works have been reported: (1) in Pseudomonas fluorescens strain 2-79, the titer of AAP reached 0.05 g/L 20 and (2) in P. chlororaphis HT66, the production of AAP reached 728.62 mg/L in 72 h through genetic engineering and culture optimization strategies.…”

Section: Introductionmentioning

confidence: 99%

De Novo Biosynthesis and Whole-Cell Catalytic Production of 2-Acetamidophenol in Escherichia coli

Hou

Feng

Xian

et al. 2021

J. Agric. Food Chem.

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2-Acetamidophenol (AAP) is an aromatic product with promising activities in agricultural applications and medical research. At present, AAP is synthesized by chemical methods from nonrenewable fossil fuel resources, which cause environmental pollution and the reaction conditions are harsh. In this study, we constructed the artificial biosynthetic pathway of AAP with five different expressed proteins in Escherichia coli for the first time. By introducing the hydrogen peroxide degrading enzyme catalase and improving cell tolerance to toxic intermediates or products, the yield of AAP reached 33.54 mg/L using shaking-flask culture. The best-engineered strain could produce 568.57 mg/L AAP by fed-batch fermentation from glucose and precursor (2-aminophenol, 2-AP) addition. Furthermore, a one-pot whole-cell cascade biocatalytic pathway to AAP and analogues was developed and optimized. This method can efficiently produce 1.8 g/L AAP using the methyl anthranilate hydrolysis product as the substrate. This study provides not only the de novo artificial biosynthetic pathway of AAP in E. coli but also a promising sustainable and efficient strategy to enable the synthesis of AAP on a gram scale.

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Formation of N-acetylaminophenol from anthranilic acid by Pseudomonas pyrrocinia ATCC15958

Cited by 2 publications

References 8 publications

Identification of new arylamine N-acetyltransferases and enhancing 2-acetamidophenol production in Pseudomonas chlororaphis HT66

Identification of new arylamine N-acetyltransferases and enhancing 2-acetamidophenol production in Pseudomonas chlororaphis HT66

De Novo Biosynthesis and Whole-Cell Catalytic Production of 2-Acetamidophenol in Escherichia coli

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