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Microorganisms and Methods for the Biosynthesis of Aromatics, 2,4

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Microorganisms and Methods for the Biosynthesis of Aromatics, 2,4 (19) TZZ Z¥Z_T (11) EP 2 607 340 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C07C 11/167 (2006.01) C12N 15/52 (2006.01) 06.09.2017 Bulletin 2017/36 C12N 1/15 (2006.01) C12N 1/19 (2006.01) C12N 1/21 (2006.01) C12P 5/00 (2006.01) (2006.01) (2006.01) (21) Application number: 13154607.9 C12P 5/02 C12P 7/16 C12P 7/40 (2006.01) C12P 7/62 (2006.01) C12P 9/00 (2006.01) (22) Date of filing: 26.07.2011 (54) Microorganisms and methods for the biosynthesis of aromatics, 2,4-pentadienoate and 1,3-butadiene Microorganismen und Verfahren zur Biosynthese von Aromaten 2,4-Pentadienoat und 1,3-Butadien Microorganismes et procédé de biosynthèse d’hydrocarbures aromatiques 2,4-pentadienoate et 1,3-butadiène (84) Designated Contracting States: (56) References cited: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB WO-A1-2009/111513 US-A1- 2011 300 597 GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR • Anonymous: "1,3-butadiene", Scorecard Goodguide , 16 August 2001 (2001-08-16), (30) Priority: 26.07.2010 US 367792 P XP002694708, Retrieved from the Internet: 27.07.2010 US 368223 P URL:http://scorecard.goodguide.com/chemica 09.09.2010 US 381407 P l-profiles/html/13butadiene.html [retrieved on 2013-04-02] (43) Date of publication of application: • DIETMARH PIEPER ET AL: "Engineering bacteria 26.06.2013 Bulletin 2013/26 for bioremediation", CURRENT OPINION IN BIOTECHNOLOGY, vol. 11, no. 3, 1 June 2000 (62) Document number(s) of the earlier application(s) in (2000-06-01), pages262-270, XP055058117, ISSN: accordance with Art. 76 EPC: 0958-1669, DOI: 10.1016/S0958-1669(00)00094-X 11740777.5 • KUZMA JENNIFER ET AL: "Bacteria produce the volatile hydrocarbon isoprene", CURRENT (73) Proprietor: Genomatica, Inc. MICROBIOLOGY, vol. 30, no. 2, 1 February 1995 San Diego, CA 92121 (US) (1995-02-01), pages 97-103, XP009107794, SPRINGER, NEW YORK, NY, US ISSN: 0343-8651, (72) Inventors: DOI: 10.1007/BF00294190 • Osterhout, Robin E. • SHINGLER V ET AL: "NUCLEOTIDE SEQUENCE San Diego, CA 92121 (US) AND FUNCTIONAL ANALYSIS OF THE • Burgard, Anthony P. COMPLETE PHENOL-3 4-DIMETHYLPHENOL San Diego, CA 92121 (US) CATABOLIC PATHWAY OF PSEUDOMONAS-SP •Pharkya,Priti STRAIN CF600", JOURNAL OF BACTERIOLOGY, San Diego, CA 92121 (US) vol. 174, no.3, 1 January 1992 (1992-01-01), pages • Burk, Mark J. 711-724, XP002542017, AMERICAN SOCIETY San Diego, CA 92121 (US) FOR MICROBIOLOGY, WASHINGTON, DC; US ISSN: 0021-9193 (74) Representative: Hoffmann Eitle • LOFROTH G ET AL: "CHARACTERIZATION OF Patent- und Rechtsanwälte PartmbB ENVIRONMENTAL TOBACCO SMOKE", Arabellastraße 30 ENVIRONMENTAL SCIENCE AND 81925 München (DE) TECHNOLOGY, vol. 23, no. 5, 1989, pages 610-614, ISSN: 0013-936X Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 607 340 B1 Printed by Jouve, 75001 PARIS (FR) EP 2 607 340 B1 Description BACKGROUND OF THE INVENTION 5 [0001] The present disclosure relates generally to biosynthetic processes, and more specifically to organisms having toluene, benzene, p-toluate, terephthalate, (2-hydroxyl-3-methyl-4-oxobutoxy)phosphonate, (2-hydroxy-4-oxobu- toxy)phosphonate, benzoate, styrene, 2,4-pentadienoate, 3-butene-1ol or 1,3-butadiene biosynthetic capability. [0002] Toluene is a common solvent that has replaced benzene due to benzene’s greater carcinogenicity and is an industrial feedstock and used in the manufacture of TNT, polyurethane foam, benzaldehyde and benzoic acid. Toluene 10 is a byproduct in the manufacture of gasoline and exists in small concentrations in crude oil. [0003] Benzene is often used as an intermediate to make other chemicals. Its most widely-produced derivatives include styrene, which is used to make polymers and plastics, phenol for resins and adhesives, via cumene, and cyclohexane, which is used in the manufacture of Nylon. Benzene is also used to make some types of rubbers, lubricants, dyes, detergents, drugs, explosives, napalm and pesticides. Benzene production in the petroleum industry is made by various 15 energy intensive processes including, catalytic preforming, toluene hydrodealkylation, toluene disproportionation, and steam cracking. [0004] Styrene is the precursor to polystyrene and numerous copolymers. Styrene based products include, acrylonitrile 1,3-butadiene styrene (ABS), styrene-1,3-butadiene (SBR) rubber, styrene-1,3-butadiene latex, SIS (styrene-isoprene- styrene), S-EB-S (styrene-ethylene/butylene-styrene), styrene-divinylbenzene (S-DVB), and unsaturated polyesters. 20 These materials are used in rubber, plastic, insulation, fiberglass, pipes, automobile and boat parts, food containers, and carpet backing. [0005] Styrene is most commonly produced by the catalytic dehydrogenation of ethylbenzene. Ethylbenzene is mixed in the gas phase with 10-15 times its volume in high-temperature steam, and passed over a solid catalyst bed. Most ethylbenzene dehydrogenation catalysts are based on iron(III) oxide, promoted by several percent potassium oxide or 25 potassium carbonate. Steam serves several roles in this reaction. It is the source of heat for powering the endothermic reaction, and it removes coke that tends to form on the iron oxide catalyst through the water gas shift reaction. The potassium promoter enhances this decoking reaction. The steam also dilutes the reactant and products, shifting the position of chemical equilibrium towards products. A typical styrene plant consists of two or three reactors in series, which operate under vacuum to enhance the conversion and selectivity. Typical per-pass conversions are ca. 65% for 30 two reactors and 70-75% for three reactors. [0006] Over 25 billion pounds of 1,3-butadiene (or just butadiene or BD) are produced annually and is applied in the manufacture of polymers such as synthetic rubbers and ABS resins, and chemicals such as hexamethylenediamine and 1,4-butanediol. 1,3-butadiene is typically produced as a by-product of the steam cracking process for conversion of petroleum feedstocks such as naphtha, liquefied petroleum gas, ethane or natural gas to ethylene and other olefins. 35 The ability to manufacture 1,3-butadiene from alternative and/or renewable feedstocks would represent a major advance in the quest for more sustainable chemical production processes [0007] One possible way to produce 1,3-butadiene renewably involves fermentation of sugars or other feedstocks to produce diols, such as 1,4-butanediol or 1,3-butanediol, which are separated, purified, and then dehydrated to 1,3- butadiene in a second step involving metal-based catalysis. Direct fermentative production of 1,3-butadiene from re- 40 newable feedstocks would obviate the need for dehydration steps and 1,3-butadiene gas (bp -4.4°C) would be contin- uously emitted from the fermenter and readily condensed and collected. Developing a fermentative production process would eliminate the need for fossil-based 1,3-butadiene and would allow substantial savings in cost, energy, and harmful waste and emissions relative to petrochemically-derived 1,3-butadiene. [0008] 2,4-Pentadienoate is a useful substituted butadiene derivative in its own right and a valuable intermediate en 45 route to other substituted 1,3-butadiene derivatives, including, for example, 1-carbamoyl-1,3-butadienes which are ac- cessible via Curtius rearrangement. The resultant N-proteeted-1,3-butadiene derivatives can be used in Diels alder reactions for the preparation of substituted anilines. 2,4-Pentadienoate can be used in the preparation of various polymers and co-polymers. [0009] Terephthalate (also known as terephthalic acid and PTA) is the immediate precursor of polyethylene tereph- 50 thalate (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 naphtba. Xylene is also obtained from the pyrolysis gasoline stream in a naphtha steam cracker and by toluene disproportion. 55 [0010] Cost-effective methods for generating renewable PTA have not yet been developed to date. PTA, toluene and other aromatic precursors are naturally degraded by some bacteria. 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 ofknown enzymes to date. 2 EP 2 607 340 B1 [0011] A promising precursor for PTA is p-toluate, also known as p-methylbenzoate. P-Toluate is an intermediate in some industrial processes for the oxidation of p-xylene to PTA. It is also an intermediate for polymer stabilizers, pesticides, light sensitive compounds, animal feed supplements and other organic chemicals. Only slightly soluble in aqueous solution, p-toluate is a solid at physiological temperatures, with a melting point of 275°C. Microbial catalysts for synthe- 5 sizing this compound from sugar feedstocks have not been described to date. WO 2009/111513 A1 describes engineered CO2 fixing microorganism producing carbon-based products of interest. [0012] Thus, there exists a need for alternative methods for effectively producing commercial quantities of compounds suchas styrene, 2,4-pentadienoate,1,3-butadiene, p-toluate, terephthalate, benzene and toluene. The present disclosure satisfies this need and provides related advantages as well.
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