Aerobic biosynthesis of hydrocinnamic acids in Escherichia coli with a strictly oxygen-sensitive enoate reductase

Sun, Jing; Lin, Yuheng; Shen, Xiaolin; Jain, Rachit; Sun, Xinxiao; Yuan, Qipeng; Yan, Yajun

doi:10.1016/j.ymben.2016.02.002

Cited by 45 publications

(51 citation statements)

References 33 publications

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“…During preparation of this manuscript, it was reported that a 2-enoate reductase, CaEr, from Clostridium acetobutylicum was able to reduce the double bond of cinnamic acid and p -coumaric acid when expressed in E. coli (Sun et al, 2016). A phloretin pathway with this DBR was therefore constructed on an HRT plasmid to create strain DBR13 and production of phloretin and naringenin was compared to strains DBR12 (control) and DBR2, overexpressing ScTSC13 .…”

Section: Resultsmentioning

confidence: 99%

Metabolic engineering of Saccharomyces cerevisiae for de novo production of dihydrochalcones with known antioxidant, antidiabetic, and sweet tasting properties

Eichenberger

Lehka

Folly

et al. 2017

Metabolic Engineering

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Dihydrochalcones are plant secondary metabolites comprising molecules of significant commercial interest as antioxidants, antidiabetics, or sweeteners. To date, their heterologous biosynthesis in microorganisms has been achieved only by precursor feeding or as minor by-products in strains engineered for flavonoid production. Here, the native ScTSC13 was overexpressed in Saccharomyces cerevisiae to increase its side activity in reducing p-coumaroyl-CoA to p-dihydrocoumaroyl-CoA. De novo production of phloretin, the first committed dihydrochalcone, was achieved by co-expression of additional relevant pathway enzymes. Naringenin, a major by-product of the initial pathway, was practically eliminated by using a chalcone synthase from barley with unexpected substrate specificity. By further extension of the pathway from phloretin with decorating enzymes with known specificities for dihydrochalcones, and by exploiting substrate flexibility of enzymes involved in flavonoid biosynthesis, de novo production of the antioxidant molecule nothofagin, the antidiabetic molecule phlorizin, the sweet molecule naringin dihydrochalcone, and 3-hydroxyphloretin was achieved.

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Section: Resultsmentioning

confidence: 99%

Metabolic engineering of Saccharomyces cerevisiae for de novo production of dihydrochalcones with known antioxidant, antidiabetic, and sweet tasting properties

Eichenberger

Lehka

Folly

et al. 2017

Metabolic Engineering

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“…4,54,78 Phenylalanine ammonia lyase (PAL) and tyrosine ammonia lyase (TAL) catalyze the reactions for converting L-Phe and L-Tyr to trans-cinnamic acid and p-hydroxycinnamic acid, respectively. 50 Flavonoids, stilbenoids and alkaloids are naturally produced in the plant via a secondary metabolic pathway. Moreover, an alternative fermentation pathway for production of trans-cinnamic acid via D-phenyllactic acid was recently reported and the titer is 11-fold higher than that of trans-cinnamic acid production using a PAL-dependent pathway.…”

Section: -Phenylethanol and Tyrosol [2-(4-hydroxyphenyl) Ethanol]mentioning

confidence: 99%

“…49,57 The C C bond of trans-cinnamic acid and p-hydroxycinnamic acid can be reduced by 2-enoate reductase (2ER) to generate 3-phenylpropionic acid and 3-(4-hydroxyphenyl)propionic acid in E. coli even under aerobic conditions, respectively. 50 Flavonoids, stilbenoids and alkaloids are naturally produced in the plant via a secondary metabolic pathway. However, the low content of these compounds in plant tissue and lack of efficient extraction methods make it difficult to efficiently produce them.…”

Section: Production Of L-tyr Derivativesmentioning

confidence: 99%

Expanding the repertoire of aromatic chemicals by microbial production

Song

Chen

et al. 2018

J of Chemical Tech & Biotech

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Microbial production of aromatic chemicals would greatly contribute to solving the problems with fossil resource supply and environmentally sustainable development. Engineering and extending the shikimate/aromatic amino acid biosynthetic pathways are important routes for microbial production of various aromatic chemicals. With advances in metabolic engineering and synthetic biology, we can broaden the product spectrum and obtain several valuable and novel aromatic chemicals from renewable feedstocks. Here, in this review, the latest research progress on microbial production of various aromatic chemicals, and recent metabolic engineering and synthetic biology strategies targeting the central carbon metabolism, the shikimate and aromatic amino acid biosynthetic pathways are summarized and discussed. This work aims to provide some valuable tips for the construction of cost‐effective engineered strains for producing various aromatic chemicals. © 2018 Society of Chemical Industry

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“…In recent years, metabolic engineering production of many highvalue products, such as terpenoids (Leonard et al, 2010;Paddon et al, 2013), coumarins (Lin et al, 2013a(Lin et al, , 2013b, phenylpropanoic acids (Sun et al, 2016), monolignols (Chen et al, 2017), flavonoids (Leonard et al, 2006;Santos et al, 2011;Wang et al, 2016a), amino acids (Becker et al, 2011;Zhang et al, 2010), isoprenes (Alper et al, 2005), alkanes (Choi and Lee, 2013), fatty acids , and other biofuels (Bhan et al, 2013;Yim et al, 2011;Zhang et al, 2008) has been achieved. However, there is no natural and efficient pathway existing to achieve GA biosynthesis from simple carbon sources, primarily because no natural hydroxylase can catalyze 3,4dihydroxybenzoic acid (3,4-DHBA) into GA.…”

Section: Introductionmentioning

confidence: 99%

Rational engineering of p‐hydroxybenzoate hydroxylase to enable efficient gallic acid synthesis via a novel artificial biosynthetic pathway

Chen

Shen

Wang

et al. 2017

Biotech & Bioengineering

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Gallic acid (GA) is a naturally occurring phytochemical that has strong antioxidant and antibacterial activities. It is also used as a potential platform chemical for the synthesis of diverse high-value compounds. Hydrolytic degradation of tannins by acids, bases or microorganisms serves as a major way for GA production, which however, might cause environmental pollution and low yield and efficiency. Here, we report a novel approach for efficient microbial production of GA. First, structure-based rational engineering of PobA, a p-hydroxybenzoate hydroxylase from Pseudomonas aeruginosa, generated a new mutant, Y385F/T294A PobA, which displayed much higher activity toward 3,4-dihydroxybenzoic acid (3,4-DHBA) than the wild-type and any other reported mutants. Remarkably, expression of this mutant in Escherichia coli enabled generation of 1149.59 mg/L GA from 1000 mg/L 4-hydroxybenzoic acid (4-HBA), representing a 93% molar conversion ratio. Based on that, we designed and reconstituted a novel artificial biosynthetic pathway of GA and achieved 440.53 mg/L GA production from simple carbon sources in E. coli. Further enhancement of precursor supply through reinforcing shikimate pathway was able to improve GA de novo production to 1266.39 mg/L in shake flasks. Overall, this study not only led to the development of a highly active PobA variant for hydroxylating 3,4-DHBA into GA via structure-based protein engineering approach, but also demonstrated a promising pathway for bio-based manufacturing of GA and its derived compounds. Biotechnol. Bioeng. 2017;114: 2571-2580. © 2017 Wiley Periodicals, Inc.

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Aerobic biosynthesis of hydrocinnamic acids in Escherichia coli with a strictly oxygen-sensitive enoate reductase

Cited by 45 publications

References 33 publications

Metabolic engineering of Saccharomyces cerevisiae for de novo production of dihydrochalcones with known antioxidant, antidiabetic, and sweet tasting properties

Metabolic engineering of Saccharomyces cerevisiae for de novo production of dihydrochalcones with known antioxidant, antidiabetic, and sweet tasting properties

Expanding the repertoire of aromatic chemicals by microbial production

Rational engineering of p‐hydroxybenzoate hydroxylase to enable efficient gallic acid synthesis via a novel artificial biosynthetic pathway

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