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Microorganisms and methods for the biosynthesis of p-toluate and terephthalate

a biosynthesis and microorganism technology, applied in the field of biosynthesis processes, can solve the problems of cost-effective methods for generating renewable pta that have not yet been developed, and the biosynthesis pathway of pta is severely limited by the properties of known enzymes

Inactive Publication Date: 2011-08-25
GENOMATICA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Cost-effective methods for generating renewable PTA have not yet been developed to date.
However, these degradation pathways typically involve monooxygenases that operate irreversibly in the degradative direction.
Hence, biosynthetic pathways for PTA are severely limited by the properties of known enzymes to date.

Method used

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  • Microorganisms and methods for the biosynthesis of p-toluate and terephthalate
  • Microorganisms and methods for the biosynthesis of p-toluate and terephthalate
  • Microorganisms and methods for the biosynthesis of p-toluate and terephthalate

Examples

Experimental program
Comparison scheme
Effect test

example i

Exemplary Pathway for Producing (2-Hydroxy-3-methyl-4-oxobutoxy)phosphonate

[0103]This example describes an exemplary pathway for producing the terephthalic acid (PTA) precursor (2-hydroxy-3-methyl-4-oxobutoxy)phosphonate (2H3M4OP).

[0104]The precursor to the p-toluate and PTA pathways is 2H3M4OP. This chemical can be derived from central metabolites glyceraldehyde-3-phosphate (G3P) and pyruvate in three enzymatic steps as shown in FIG. 1. The first two steps are native to E. coli and other organisms that utilize the methylerythritol phosphate (non-mevalonate) pathway for isoprenoid biosynthesis. Pyruvate and G3P are first condensed to form 1-deoxy-D-xylulose 5-phosphate (DXP) by DXP synthase. Subsequent reduction and rearrangement of the carbon backbone is catalyzed by DXP reductoisomerase. Finally, a novel diol dehydratase transforms 2-C-methyl-D-erythritol-4-phosphate to the p-toluate precursor 2H3M4OP.

[0105]A. 1-Deoxyxylulose-5-phosphate (DXP) synthase. Pyruvate and G3P are conden...

example ii

Exemplary Pathway for Synthesis of p-Toluate from (2-Hydroxy-3-methyl-4-oxobutoxy)phosphonate by Shikimate Pathway Enzymes

[0114]This example describes exemplary pathways for synthesis of p-toluate using shikimate pathway enzymes.

[0115]The chemical structure of p-toluate closely resembles p-hydroxybenzoate, a precursor of the electron carrier ubiquinone. 4-Hydroxybenzoate is synthesized from central metabolic precursors by enzymes in the shikimate pathway, found in bacteria, plants and fungi. The shikimate pathway is comprised of seven enzymatic steps that transform D-erythrose-4-phosphate (E4P) and phosphoenolpyruvate (PEP) to chorismate. Pathway enzymes include 2-dehydro-3-deoxyphosphoheptonate (DAHP) synthase, dehydroquinate (DHQ) synthase, DHQ dehydratase, shikimate dehydrogenase, shikimate kinase, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase and chorismate synthase. In the first step of the pathway, D-erythrose-4-phosphate and phosphoenolpyruvate are joined by DAHP syntha...

example iii

Exemplary Pathway for Enzymatic Transformation of p-Toluate to Terephthalic Acid

[0127]This example describes exemplary pathways for conversion of p-toluate to terephthalic acid (PTA).

[0128]P-toluate can be further transformed to PTA by oxidation of the methyl group to an acid in three enzymatic steps as shown in FIG. 3. The pathway is comprised of a p-toluate methyl-monooxygenase reductase, a 4-carboxybenzyl alcohol dehydrogenase and a 4-carboxybenzyl aldehyde dehydrogenase. In the first step, p-toluate methyl-monooxyngenase oxidizes p-toluate to 4-carboxybenzyl alcohol in the presence of O2. The Comamonas testosteroni enzyme (tsaBM), which also reacts with 4-toluene sulfonate as a substrate, has been purified and characterized (Locher et al., J. Bacteriol. 173:3741-3748 (1991)). 4-Carboxybenzyl alcohol is subsequently converted to an aldehyde by 4-carboxybenzyl alcohol dehydrogenase (tsaC). The aldehyde to acid transformation is catalyzed by 4-carboxybenzaldehyde dehydrogenase (tsa...

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Abstract

The invention provides non-naturally occurring microbial organisms having a (2-hydroxy-3-methyl-4-oxobutoxy)phosphonate pathway, p-toluate pathway, and / or terephthalate pathway. The invention additionally provides methods of using such organisms to produce (2-hydroxy-3-methyl-4-oxobutoxy)phosphonate pathway, p-toluate pathway or terephthalate pathway.

Description

BACKGROUND OF THE INVENTION[0001]The present invention relates generally to biosynthetic processes, and more specifically to organisms having p-toluate, terephthalate or (2-hydroxy-3-methyl-4-oxobutoxy)phosphonate biosynthetic capability.[0002]Terephthalate (also known as terephthalic acid and PTA) is the immediate precursor of polyethylene terepthalate (PET), used to make clothing, resins, plastic bottles and even as a poultry feed additive. Nearly all PTA is produced from para-xylene by oxidation in air in a process known as the Mid Century Process. This oxidation is conducted at high temperature in an acetic acid solvent with a catalyst composed of cobalt and / or manganese salts. Para-xylene is derived from petrochemical sources and is formed by high severity catalytic reforming of naphtha. Xylene is also obtained from the pyrolysis gasoline stream in a naphtha steam cracker and by toluene disproportion.[0003]Cost-effective methods for generating renewable PTA have not yet been de...

Claims

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Application Information

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IPC IPC(8): C12P9/00C12N1/00C12P7/44C12P7/40
CPCC12N9/0006C12P7/40C12Y402/01C12N9/88C12P7/62C12Y101/01267C12Y401/03C12N15/52C12P7/44C12P9/00C12N9/1022C12N9/1085C12Y101/01025C12Y202/01007C12Y205/01019C12Y205/01054C12Y207/01071C12Y401/0304C12Y402/0101C12Y402/03004C12Y402/03005C12N1/20C12P7/24
Inventor OSTERHOUT, ROBIN E.
Owner GENOMATICA INC
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