United States Patent (10) Patent No.: US 9,562,241 B2 Burk Et Al

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United States Patent (10) Patent No.: US 9,562,241 B2 Burk Et Al USOO9562241 B2 (12) United States Patent (10) Patent No.: US 9,562,241 B2 Burk et al. (45) Date of Patent: Feb. 7, 2017 (54) SEMI-SYNTHETIC TEREPHTHALIC ACID 5,487.987 A * 1/1996 Frost .................... C12N 9,0069 VLAMCROORGANISMIS THAT PRODUCE 5,504.004 A 4/1996 Guettler et all 435,142 MUCONCACID 5,521,075- W I A 5/1996 Guettler et al.a (71) Applicant: GENOMATICA, INC., San Diego, CA 3. A '95 seal. (US) 5,686,276 A 11/1997 Lafend et al. 5,700.934 A 12/1997 Wolters et al. (72) Inventors: Mark J. Burk, San Diego, CA (US); (Continued) Robin E. Osterhout, San Diego, CA (US); Jun Sun, San Diego, CA (US) FOREIGN PATENT DOCUMENTS (73) Assignee: Genomatica, Inc., San Diego, CA (US) CN 1 358 841 T 2002 EP O 494 O78 7, 1992 (*) Notice: Subject to any disclaimer, the term of this (Continued) patent is extended or adjusted under 35 U.S.C. 154(b) by 0 days. OTHER PUBLICATIONS (21) Appl. No.: 14/308,292 Abadjieva et al., “The Yeast ARG7 Gene Product is Autoproteolyzed to Two Subunit Peptides, Yielding Active (22) Filed: Jun. 18, 2014 Ornithine Acetyltransferase,” J. Biol. Chem. 275(15): 11361-11367 2000). (65) Prior Publication Data . al., “Discovery of amide (peptide) bond synthetic activity in US 2014/0302573 A1 Oct. 9, 2014 Acyl-CoA synthetase,” J. Biol. Chem. 28.3(17): 11312-11321 (2008). Aberhart and Hsu, "Stereospecific hydrogen loss in the conversion Related U.S. Application Data of H, isobutyrate to f—hydroxyisobutyrate in Pseudomonas (63) Continuation of application No. 12/851,478, filed on putida. The stereochemistry of hydroxyisobutyrate dehydrogenase.” Aug. 5, 2010, now abandoned. J. Chem. Soc. rPerkin1 I6:1404-1406 (1979). (Continued) (60) Provisional application No. 61/231,637, filed on Aug. 5, 2009. Primary Examiner — Tekchand Saidha (51) Int. Cl. (74) Attorney, Agent, or Firm — Kagan Binder, PLLC CI2N L/20 (2006.01) CI2P 7/44 (2006.01) (52) U.S. Cl. (57) ABSTRACT CPC ........................................ CI2P 7/44 (2013.01) The invention provides a non-naturally occurring microbial (58) Field of Classification Search CPC ......................................................... C12P 7/44 organism having a muconate pathway having at least one USPC .......................................................... 435/142 exogenous nucleic acid encoding a muconate pathway See application file for complete search history. enzyme expressed in a sufficient amount to produce mucon ate. The muconate pathway including an enzyme selected (56) References Cited from the group consisting of a beta-ketothiolase, a beta ketoadipyl-CoA hydrolase, a beta-ketoadipyl-CoA trans U.S. PATENT DOCUMENTS ferase, a beta-ketoadipyl-CoA ligase, a 2-fumarylacetate reductase, a 2-fumarylacetate dehydrogenase, a trans-3- SE A 1887 KSk et al. hydroxy-4-hexendioate dehydratase, a 2-fumarylacetate 3,965, 182 A 6, 1976 Worrel aminotransferase, a 2-fumarylacetate aminating oxidoreduc 4,048,196 A 9, 1977 Broecker et al. tase, a trans-3-amino-4-hexenoate deaminase, a beta-ketoa 4,082,788 A 4, 1978 Mims dipate enol-lactone hydrolase, a muconolactone isomerase, a 12:25 A i8 t al muconate cycloisomerase, a beta-ketoadipyl-CoA dehydro 4,624,920 A i? 1986 Inoue genase, a 3-hydroxyadipyl-CoA dehydratase, a 2.3-dehy 4,652,685 A 3, 1987 Cawse et al. droadipyl-CoA transferase, a 2,3-dehydroadipyl-CoA hydro 4,871,667 A 10/1989 Imada et al. lase, a 2.3-dehydroadipyl-CoA ligase, a muconate reductase, 5,079,143 A 1/1992 Klein et al. a 2-maleylacetate reductase, a 2-maleylacetate dehydroge 5.143,8345,143,833. A 9, 1992 GlassnerDatta et al. nase, a cis-3-hydroxy-4-hexendioate dehydratase, a 2-ma 5. 68,055 A 12/1992 Datta et al. leylacetate aminoatransferase, a 2-maleylacetate aminating 5,173,429 A 12/1992 Gaddy et al. oxidoreductase, a cis-3-amino-4-hexendioate deaminase, 5, 182,199 A 1/1993 Hartley and a muconate cis/trans isomerase. Other muconate path 283 A 38 S.t i.e. al. way enzymes also are provided. Additionally provided are 5,413,922. A 5/1995 Matsuyama et al. methods of producing muconate. 5,416,020 A 5, 1995 Severson et al. 5,457,040 A 10/1995 Jarry et al. 5,478,952 A 12/1995 Schwartz 13 Claims, 6 Drawing Sheets US 9,562.241 B2 Page 2 (56) References Cited 2007/025941.0 A1 11/2007 Donaldson et al. 2008. O138870 A1 6/2008 Bramucci et al. U.S. PATENT DOCUMENTS 2008.0171371 A1 7/2008 Yukawa et al. 2008. 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