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(12) United States Patent (10) Patent No.: US 9,353,390 B2 Yan Et Al

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(12) United States Patent (10) Patent No.: US 9,353,390 B2 Yan Et Al US009353390B2 (12) United States Patent (10) Patent No.: US 9,353,390 B2 Yan et al. (45) Date of Patent: May 31, 2016 (54) GENETICALLY ENGINEERED MICROBES National Center for Biotechnology Information, National Library of AND METHODS FOR PRODUCING Medicine, National Institutes of Health, GenBank Locus 4-HYDROXYCOUMARIN NP 252920. Accession No. NP 252920, "isochorismate-pyruvate lyase IPseudomonas aeruginosa PAO1),” online). Bethesda, MD (71) Applicant: University of Georgia Research retrieved on Aug. 3, 2015. Retrieved from the Internet: <URL: Foundation, Inc., Athens, GA (US) http://www.ncbi.nlm.nih.gov/protein/NP 252920. 1; 3 pgs. National Center for Biotechnology Information, National Library of (72) Inventors: Yajun Yan, Athens, GA (US); Yuheng Medicine, National Institutes of Health, GenBank Locus Lin, Marietta, GA (US) NP 415125. Accession No. NP 415125. "isochorismate synthase 1 Escherichia coli str. K-12 substr. MG 1655, online. Bethesda, (73) Assignee: University of Georgia Research MD retrieved on Aug. 3, 2015). Retrieved from the Internet: <URL: http://www.ncbi.nlm.nih.gov/protein/NP 415125.1.>; 3 pgs. Foundation, Inc., Athens, GA (US) Ajikumar et al. “Isoprenoid Pathway Optimization for Taxol Precur (*) Notice: Subject to any disclaimer, the term of this sor Overproduction in Escherichia coli" Science, Oct. 1, 2010; 330(6000):70-4. patent is extended or adjusted under 35 Anthony et al. “Optimization of the mevalonate-based isoprenoid U.S.C. 154(b) by 0 days. biosynthetic pathway in Escherichia coli for production of the anti malarial drug precursor amorpha-4,11-diene' Metab. Eng. Jan. 2009; (21) Appl. No.: 14/304,105 11(1): 13-9. Epub Aug. 12, 2008. Atsumietal. “Non-fermentative pathways for synthesis of branched (22) Filed: Jun. 13, 2014 chain higher alcohols as biofuels' Nature, Jan. 3, 2008; (65) Prior Publication Data 451(7174):86-9. 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CPC ............... CI2P 17/06 (2013.01); C07D 31 1/46 Chen et al. “Biosynthesis of salicylic acid in plants' Plant Signal Behav. 2009; 4(6):493-6. Epub Jun. 12, 2009. (2013.01); C07D 311/56 (2013.01); C12N Cohen et al. "Venous thromboembolism (VTE) in Europe. The num 15/52 (2013.01) ber of VTE events and associated morbidity and mortality” Thromb. (58) Field of Classification Search Haemost. 2007: 98(4):756-64. None Daruwala et al., “Menaquinone (vitamin K2) biosynthesis: See application file for complete search history. overexpression, purification, and characterization of a new isochorismate synthase from Escherichia coli'J. Bacteriol. 1997; (56) References Cited 179(10), 3133-8. Dhamankar et al. “Microbial chemical factories: recent advances in U.S. PATENT DOCUMENTS pathway engineering for synthesis of value added chemicals' Curr: Opin. Struct. Biol. Aug. 2011; 21(4):488-94. 4,703,004 A 10/1987 Hopp et al. 4,782,137 A 1 1/1988 Hopp et al. (Continued) 5,594,115 A 1/1997 Sharma 5,935,824 A 8/1999 Sgarlato Primary Examiner — Nashaat Nashed OTHER PUBLICATIONS (74) Attorney, Agent, or Firm — Mueting, Raasch & Gebhardt, PA. National Center for Biotechnology Information, National Library of Medicine, National Institutes of Health, GenBank Locus BAC78380, (57) ABSTRACT Accession No. BAC78380, “putative salicyl-AMP ligase Provided herein are methods for the biosynthesis of 4-hy Streptomyces sp. WA46).” online. Bethesda, MD retrieved on droxycoumarin. In one embodiment, provided herein are Aug. 3, 2015). Retrieved from the Internet: <URL: http://www.ncbi. genetically engineered microbes that include a metabolic nlm.nih.gov/protein/BAC78380.1 >; 2 pgs. pathway for the production of 4-hydroxycoumarin. Also pro National Center for Biotechnology Information, National Library of Medicine, National Institutes of Health, GenBank Locus vided are methods for using the genetically engineered NP 249690, Accession No. NP 249690, “2-heptyl-4(1H)- microbes to produce 4-hydroxycoumarin, and using the 4-hy quinolone synthase Pas Pseudomonas aeruginosa PAOl.” droxycoumarin as the starting point for the synthesis of other online. Bethesda, MD retrieved on Aug. 3, 2015). Retrieved from compounds. the Internet: <URL: http://www.ncbi.nlm.nih.gov/protein/NP 249690.1 >; 3 pgs. 19 Claims, 17 Drawing Sheets US 9,353,390 B2 Page 2 (56) References Cited Matsumoto et al. “Molecular cloning and functional analysis of the Ortho-hydroxylases of p-coumaroyl coenzyme Afferuloyl coenzyme OTHER PUBLICATIONS A involved in formation of umbelliferone and scopoletin in Sweet Gaille et al. “Salicylate biosynthesis in Pseudomonas aeruginosa. potato, Ipomoea batatas (L.) Lam.” Phytochemistry, Feb. 2012; Purification and characterization of PohB, a novel bifunctional T4:49-57. enzyme displaying isochorismate pyruvate-lyase and chorismate Melnikova, “The anticoagulants market” Nat. Rev. Drug Discov. mutase activities”.J. Biol. Chem. 2002; 277(24):21768-75. 2009; 8(5):353-4. Gao et al. “Clean and Convenient One-Pot Synthesis of Murray et al., Natural Coumarins. Occurrence, chemistry and bio 4-Hydroxycoumarin and 4-Hydroxy-2-Quinolinone Derivatives' chemistry, John Wiley & Sons Ltd., Chichester, New York; 1982. Synthetic Commun. 2010; 40:732-8. Cover page, title page and table of contents. Geissler et al., “Purification and properties of benzoate-coenzyme A Nagachar et al. “Roles of tripE2, entC and entL) in salicylic acid ligase, a Rhodopseudomonas palustris enzyme involved in the biosynthesis in Mycobacterium smegmatis” FEMS Microbiol. Lett. anaerobic degradation of benzoate” J. Bacteriol. 1988; 170(4): 1709 2010; 308(2): 159-65. 14. Nakagawa et al. 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Heit et al., “Estimated annual number of incident and recurrent, Ray et al., “Mutational analysis of the catalytic and feedback sites of non-fatal and fatal venous thromboembolism (VTE) events in the the tryptophan-sensitive 3-deoxy-D-arabino-heptuloSonate-7-phos US” Blood 106, 267a-267a (2005). phate synthase of Escherichia coli J. Bacteriol., 1988: 170:5500-6. Huo et al., "Conversion of proteins into biofuels by engineering Ro et al. “Production of the antimalarial drug precursor artemisinic nitrogen flux' Nat. Biotechnol., 2011; 29(4): 346-51. acid in engineered yeast” Nature, 2006:440(7086):940-3. Ishiyama et al., “Novel pathway of Salicylate degradation by Rogozinska et al. “Efficient "on water' organocatalytic protocol for Streptomyces sp. strain WA46” Appl. Environ. Microbiol. 2004; the synthesis of optically pure warfarin anticoagulant Green Chem. 70(3): 1297-306. 2011; 13:1155-7. Ivanov et al. “New Efficient Catalysts in the Synthesis of Warfarin Rueping et al. "A review of new developments in the Friedel-Crafts and Acenocoumarol' Arch. Pharm. (Weinheim) 1990;323(8):521-2. alkylation—From green chemistry to asymmetric catalysis' Jossek et al., “Characterization of a new feedback-resistant 3-deoxy Beilstein J. Org. Chem. 2010; 6:6. 24 pages. D-arabino-heptulosonate 7-phosphate synthase AroF of Escherichia Solis et al. "Automated design of synthetic ribosome binding sites to coli” FEMS Microbiol Lett., 2001; 202: 145-8. control protein expression” Nat. Biotechnol. 2009; 27(10):946-50. Kai et al. “Scopoletin is biosynthesized via Ortho-hydroxylation of Sambrook et al. Molecular Cloning. A Laboratory Manual. Cold feruloyl CoA by a 2-oxoglutarate-dependent dioxygenase in Spring Harbor Laboratory Press, Cold Spring Harbor, New York, Arabidopsis thaliana' Plant J. 2008; 55(6):989-9. 2012. Cover page, title page, table of contents. 34 pages. Kikuchi et al. “Mutational analysis of the feedback sites of Santos et al. 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