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(12) United States Patent (10) Patent No.: US 9,580,731 B2 B0tes Et Al

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(12) United States Patent (10) Patent No.: US 9,580,731 B2 B0tes Et Al USOO9580731B2 (12) United States Patent (10) Patent No.: US 9,580,731 B2 B0tes et al. (45) Date of Patent: Feb. 28, 2017 (54) METHODS OF PRODUCING 7-CARBON 8,361,769 B1 1/2013 Koch et al. CHEMICALS VA C1 CARBON CHAIN 200-83 R 58. et al ELONGATIONASSOCATED WITH 2010.0035309 A1 2, 2010 Rh et al. COENZYME B SYNTHESIS 2010/0151536 A1 6/2010 Baynes et al. 2010/0203600 A1 8, 2010 Dubois (71) Applicant: INVISTA North America S.ár.l., 2010/02986 12 A1 11/2010 Behrouzian et al. Wilmington, DE (US) 2010. 0317069 A1 12/2010 Burk et al. 2011 0171699 A1 7/2011 Raemakers-Franken et al. (72) Inventors: Adriana Leonora Botes, Rosedale East 58.263 A. 1939 El (GB); Alex Van Eck Conradie, 2012/0101009 A1 4/2012 Beatty Eaglescliffe (GB); Changlin Chen, 2013,0065279 A1 3, 2013 Burk et al. Ingleby Barwick (GB); Paul S. 2013,0183728 A1 7/2013 Botes 2013,0210.090 A1 8, 2013 Pearlman et al. Pearlman, Thornton, PA (US) 2013/0217081 A1 8/2013 Pearlman et al. 2013,0224807 A1 8, 2013 Pearlman et al. (73) Assignee: INVISTA NORTH AMERICA 2013/0267012 A1 10, 2013 Steen et al. S.A.R.L., Wilmington, DE (US) 2014/0186902 A1 7, 2014 Botes et al. 2014/O186904 A1 7/2014 Botes et al. (*) Notice: Subject to any disclaimer, the term of this 338E. A. 23: s al patent 1s lists adjusted under 35 2014/0193864 A1 7, 2014 BotesOCS et al.a U.S.C. 154(b) by 0 days. 2014/0193865 A1 7, 2014 Botes et al. 2014,01969.04 A1 7/2014 Fontenelle et al. (21) Appl. No.: 14/138,971 2014,0199.737 A1 7, 2014 Botes et al. (22) Filed: Dec.e Afa23, 9 2013 (Continued) FOREIGN PATENT DOCUMENTS (65) Prior Publication Data US 2014/0193863 A1 Jul. 10, 2014 Wo woooooo; "38. Related U.S. Application Data (Continued) (60) Provisional application No. 61/747,406, filed on Dec. OTHER PUBLICATIONS 31, 2012, provisional application No. 61/829,088, filed on May 30, 2013. Kizer L. et al. Application of Functional Genomics to Pathway Optimization for Increased Isoprenoid Production. 2008. Applied (51) Int. Cl. and Environmental Microbiology, vol. 74, No. 10. p. 3229-3241.* Prather KLJ et al. De novo biosynthetic pathways: rational design CI2P I3/00 (2006.01) of microbial chemical factories. 2008. Current Opinion in Biotech CI2P 7/18 (2006.01) nology. 19:468-474.* CI2P 7/42 (2006.01) “Enterococcus faecalis V583 bifuntional acetaldehyde-CoA/Alco CI2P 7/44 (2006.01) hol Dehydrogenase.” biocyc.org, retrieved on Jun. 19, 2014. http:// CI2N 15/52 (2006.01) biocyc.org/EFAE226185/N EW-IMAGE?type=ENZYM (52) U.S. Cl. E&object-GH11-877-MONOMER, 9 pages. “Information on EC 1.2.1.57—butanal dehydrogenase,” brenda CPC ............ CI2P 13/001 (2013.01); C12N 15/52 enzymes.org, retrieved on Jun. 19, 2014. http:// brenda-en (2013.01); CI2P 7/18 (2013.01): CI2P 7/42 Zymes.org/php/result flat.php4?ecno=1.2.1.57, 6 pages. (2013.01); C12P 7/44 (2013.01); C12P 13/005 “BRENDA The comprehensive Enzyme Information System.” (2013.01) Jul. 2011, retrieved on Sep. 19, 2014. http://web.archive.org/web/ (58) Field of Classification Search 2011 1009205602/http://www.brenda-enzymes.org/, 1 page. None (Continued) See application file for complete search history. Primary Examiner — Paul Holland (56) References Cited (74) Attorney, Agent, or Firm — Finnegan, Henderson, U.S. PATENT DOCUMENTS Farabow, Garrett & Dunner, LLP, Carla A. Mouta-Bellum 2.439,513. A 4, 1948 Hambleta et alla (57) ABSTRACT 2,557,282 A 6, 1951 Hamblet et al. This document describes biochemical pathways for produc 3. Sg A 3. 8. s Jr. et al ing pimelic acid, 7-aminoheptanoic acid, 7-hydroxyhep 2970 10 A 2/1961 Gilby, Jr. et al. tanoic acid, heptamethylenediamine or 1,7-heptanediol by 3,023,238 A 2, 1962 Chapman et al. forming One Or tWO terminal functional groups, each CO 3,338,959 A 8, 1967 Sciance et al. prised of carboxyl, amine or hydroxyl group, in a C7 3,365.490 A 1, 1968 Arthur et al. aliphatic backbone substrate. These pathways, metabolic 3,515,751 A g 1970 re 1 engineering and cultivation Strategies described herein rely 3.653. A 1923 Aka et al. on the C1 elongation enzymes or homolog associated with 6.255.451 B1 7/2001 Kochet al. coenzyme B biosynthesis. 6,372,939 B1 4/2002 Bunnel et al. 8,088,607 B2 1/2012 Burgard et al. 16 Claims, 26 Drawing Sheets US 9,580,731 B2 Page 2 (56) References Cited Binieda et al., “Purification, characterization, DNA Sequence and cloning of a pimeloyl-CoA synthetase from Pseudomonas medocin U.S. PATENT DOCUMENTS 35,” Biochem J., 1999, 340:793-801. 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