Microbial production of cis,cis-muconic acid

Yoshikawa, Nobuji; Mizuno, Sumiko; Ohta, Kazumi; Suzuki, Migaku

doi:10.1016/0168-1656(90)90009-z

Cited by 37 publications

(16 citation statements)

References 4 publications

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“…Muconic acid is the synthetic precursor of adipic acid and can also be used for the production of new functional resins, pharmaceuticals, and agrichemicals (42). In this study, we designed a novel pathway and successfully achieved the production of muconic acid from simple carbon sources.…”

Section: Discussionmentioning

confidence: 99%

A Novel Muconic Acid Biosynthesis Approach by Shunting Tryptophan Biosynthesis via Anthranilate

Sun

Lin

Huang

et al. 2013

Appl Environ Microbiol

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cMuconic acid is the synthetic precursor of adipic acid, and the latter is an important platform chemical that can be used for the production of nylon-6,6 and polyurethane. Currently, the production of adipic acid relies mainly on chemical processes utilizing petrochemicals, such as benzene, which are generally considered environmentally unfriendly and nonrenewable, as starting materials. Microbial synthesis from renewable carbon sources provides a promising alternative under the circumstance of petroleum depletion and environment deterioration. Here we devised a novel artificial pathway in Escherichia coli for the biosynthesis of muconic acid, in which anthranilate, the first intermediate in the tryptophan biosynthetic branch, was converted to catechol and muconic acid by anthranilate 1,2-dioxygenase (ADO) and catechol 1,2-dioxygenase (CDO), sequentially and respectively. First, screening for efficient ADO and CDO from different microbial species enabled the production of gram-per-liter level muconic acid from supplemented anthranilate in 5 h. To further achieve the biosynthesis of muconic acid from simple carbon sources, anthranilate overproducers were constructed by overexpressing the key enzymes in the shikimate pathway and blocking tryptophan biosynthesis. In addition, we found that introduction of a strengthened glutamine regeneration system by overexpressing glutamine synthase significantly improved anthranilate production. Finally, the engineered E. coli strain carrying the full pathway produced 389.96 ؎ 12.46 mg/liter muconic acid from simple carbon sources in shake flask experiments, a result which demonstrates scale-up potential for microbial production of muconic acid.

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Section: Discussionmentioning

confidence: 99%

A Novel Muconic Acid Biosynthesis Approach by Shunting Tryptophan Biosynthesis via Anthranilate

Sun

Lin

Huang

et al. 2013

Appl Environ Microbiol

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“…The systematic extension of the REEX strategy (5) to WSA's in general, in combination with the pH experiments allow for a better understanding of the mechanism of the reactive extraction itself. Within this work, CCMA was chosen as example, due to its relevance for the chemical industry as a potential precursor for adipic acid [34][35][36] and other polymerization and esterification reactions [37,38]. The biocatalytic production of CCMA using whole-cell biocatalysis, is well described in recent literature [34,[36][37][38][39][40].…”

Section: Introductionmentioning

confidence: 99%

Recovery of cis,cis-muconic acid from organic phase after reactive extraction

Gorden

Zeiner

Sadowski

et al. 2016

Separation and Purification Technology

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“…One possible biochemical route is via cis,cis-muconic acid (CCM), which can be hydrogenated to adipic acid (38). Several bacteria are known to convert aromatic compounds into CCM (37,53). The first synthetic route using renewable resources like glucose has been established in Escherichia coli (10) (Fig.…”

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confidence: 99%

Biosynthesis of cis , cis -Muconic Acid and Its Aromatic Precursors, Catechol and Protocatechuic Acid, from Renewable Feedstocks by Saccharomyces cerevisiae

Weber

Brückner

Weinreb

et al. 2012

Appl Environ Microbiol

155

170

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Adipic acid is a high-value compound used primarily as a precursor for the synthesis of nylon, coatings, and plastics. Today it is produced mainly in chemical processes from petrochemicals like benzene. Because of the strong environmental impact of the production processes and the dependence on fossil resources, biotechnological production processes would provide an interesting alternative. Here we describe the first engineered Saccharomyces cerevisiae strain expressing a heterologous biosynthetic pathway converting the intermediate 3-dehydroshikimate of the aromatic amino acid biosynthesis pathway via protocatechuic acid and catechol into cis,cis-muconic acid, which can be chemically dehydrogenated to adipic acid. The pathway consists of three heterologous microbial enzymes, 3-dehydroshikimate dehydratase, protocatechuic acid decarboxylase composed of three different subunits, and catechol 1,2-dioxygenase. For each heterologous reaction step, we analyzed several potential candidates for their expression and activity in yeast to compose a functional cis,cis-muconic acid synthesis pathway. Carbon flow into the heterologous pathway was optimized by increasing the flux through selected steps of the common aromatic amino acid biosynthesis pathway and by blocking the conversion of 3-dehydroshikimate into shikimate. The recombinant yeast cells finally produced about 1.56 mg/liter cis,cis-muconic acid.

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Microbial production of cis,cis-muconic acid

Cited by 37 publications

References 4 publications

A Novel Muconic Acid Biosynthesis Approach by Shunting Tryptophan Biosynthesis via Anthranilate

A Novel Muconic Acid Biosynthesis Approach by Shunting Tryptophan Biosynthesis via Anthranilate

Recovery of cis,cis-muconic acid from organic phase after reactive extraction

Biosynthesis of cis , cis -Muconic Acid and Its Aromatic Precursors, Catechol and Protocatechuic Acid, from Renewable Feedstocks by Saccharomyces cerevisiae

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