CA2848253C - Production of odd chain fatty acid derivatives in recombinant microbial cells - Google Patents

Production of odd chain fatty acid derivatives in recombinant microbial cells Download PDF

Info

Publication number
CA2848253C
CA2848253C CA2848253A CA2848253A CA2848253C CA 2848253 C CA2848253 C CA 2848253C CA 2848253 A CA2848253 A CA 2848253A CA 2848253 A CA2848253 A CA 2848253A CA 2848253 C CA2848253 C CA 2848253C
Authority
CA
Canada
Prior art keywords
activity
microbial cell
polypeptide
fatty acid
coa
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CA2848253A
Other languages
English (en)
French (fr)
Other versions
CA2848253A1 (en
Inventor
Grace J. Lee
John R. Haliburton
Zhihao Hu
Andreas W. Schirmer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Genomatica Inc
Original Assignee
REG Life Sciences LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by REG Life Sciences LLC filed Critical REG Life Sciences LLC
Publication of CA2848253A1 publication Critical patent/CA2848253A1/en
Application granted granted Critical
Publication of CA2848253C publication Critical patent/CA2848253C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6409—Fatty acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/126—Acids containing more than four carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/20—Bacteria; Culture media therefor
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/11—DNA or RNA fragments; Modified forms thereof; Non-coding nucleic acids having a biological activity
    • C12N15/52—Genes encoding for enzymes or proenzymes
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/63—Introduction of foreign genetic material using vectors; Vectors; Use of hosts therefor; Regulation of expression
    • C12N15/70—Vectors or expression systems specially adapted for E. coli
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/0004—Oxidoreductases (1.)
    • C12N9/0006—Oxidoreductases (1.) acting on CH-OH groups as donors (1.1)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/0004—Oxidoreductases (1.)
    • C12N9/0008—Oxidoreductases (1.) acting on the aldehyde or oxo group of donors (1.2)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/1003—Transferases (2.) transferring one-carbon groups (2.1)
    • C12N9/1018—Carboxy- and carbamoyl transferases (2.1.3)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/1025—Acyltransferases (2.3)
    • C12N9/1029—Acyltransferases (2.3) transferring groups other than amino-acyl groups (2.3.1)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/12—Transferases (2.) transferring phosphorus containing groups, e.g. kinases (2.7)
    • C12N9/1205—Phosphotransferases with an alcohol group as acceptor (2.7.1), e.g. protein kinases
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/12—Transferases (2.) transferring phosphorus containing groups, e.g. kinases (2.7)
    • C12N9/1217—Phosphotransferases with a carboxyl group as acceptor (2.7.2)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/14—Hydrolases (3)
    • C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/14—Hydrolases (3)
    • C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
    • C12N9/18—Carboxylic ester hydrolases (3.1.1)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/88—Lyases (4.)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/90—Isomerases (5.)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y101/00—Oxidoreductases acting on the CH-OH group of donors (1.1)
    • C12Y101/01—Oxidoreductases acting on the CH-OH group of donors (1.1) with NAD+ or NADP+ as acceptor (1.1.1)
    • C12Y101/01001—Alcohol dehydrogenase (1.1.1.1)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y101/00—Oxidoreductases acting on the CH-OH group of donors (1.1)
    • C12Y101/01—Oxidoreductases acting on the CH-OH group of donors (1.1) with NAD+ or NADP+ as acceptor (1.1.1)
    • C12Y101/01003—Homoserine dehydrogenase (1.1.1.3)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y101/00—Oxidoreductases acting on the CH-OH group of donors (1.1)
    • C12Y101/01—Oxidoreductases acting on the CH-OH group of donors (1.1) with NAD+ or NADP+ as acceptor (1.1.1)
    • C12Y101/01085—3-Isopropylmalate dehydrogenase (1.1.1.85)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y102/00—Oxidoreductases acting on the aldehyde or oxo group of donors (1.2)
    • C12Y102/01—Oxidoreductases acting on the aldehyde or oxo group of donors (1.2) with NAD+ or NADP+ as acceptor (1.2.1)
    • C12Y102/0105—Long-chain-fatty-acyl-CoA reductase (1.2.1.50)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y102/00—Oxidoreductases acting on the aldehyde or oxo group of donors (1.2)
    • C12Y102/01—Oxidoreductases acting on the aldehyde or oxo group of donors (1.2) with NAD+ or NADP+ as acceptor (1.2.1)
    • C12Y102/0108—Long-chain acyl-[acyl-carrier-protein] reductase (1.2.1.80)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y201/00—Transferases transferring one-carbon groups (2.1)
    • C12Y201/03—Carboxy- and carbamoyltransferases (2.1.3)
    • C12Y201/03001—Methylmalonyl-CoA carboxytransferase (2.1.3.1)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y203/00—Acyltransferases (2.3)
    • C12Y203/01—Acyltransferases (2.3) transferring groups other than amino-acyl groups (2.3.1)
    • C12Y203/01041—Beta-ketoacyl-acyl-carrier-protein synthase I (2.3.1.41)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y203/00—Acyltransferases (2.3)
    • C12Y203/01—Acyltransferases (2.3) transferring groups other than amino-acyl groups (2.3.1)
    • C12Y203/01182—(R)-Citramalate synthase (2.3.1.182)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y207/00—Transferases transferring phosphorus-containing groups (2.7)
    • C12Y207/01—Phosphotransferases with an alcohol group as acceptor (2.7.1)
    • C12Y207/01039—Homoserine kinase (2.7.1.39)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y207/00—Transferases transferring phosphorus-containing groups (2.7)
    • C12Y207/02—Phosphotransferases with a carboxy group as acceptor (2.7.2)
    • C12Y207/02004—Aspartate kinase (2.7.2.4)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y301/00—Hydrolases acting on ester bonds (3.1)
    • C12Y301/01—Carboxylic ester hydrolases (3.1.1)
    • C12Y301/01067—Fatty-acyl-ethyl-ester synthase (3.1.1.67)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y301/00—Hydrolases acting on ester bonds (3.1)
    • C12Y301/02—Thioester hydrolases (3.1.2)
    • C12Y301/02001—Acetyl-CoA hydrolase (3.1.2.1)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y401/00—Carbon-carbon lyases (4.1)
    • C12Y401/01—Carboxy-lyases (4.1.1)
    • C12Y401/01041—Methylmalonyl-CoA decarboxylase (4.1.1.41)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y401/00—Carbon-carbon lyases (4.1)
    • C12Y401/03—Oxo-acid-lyases (4.1.3)
    • C12Y401/03022—Citramalate lyase (4.1.3.22)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y402/00—Carbon-oxygen lyases (4.2)
    • C12Y402/01—Hydro-lyases (4.2.1)
    • C12Y402/01033—3-Isopropylmalate dehydratase (4.2.1.33)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y402/00—Carbon-oxygen lyases (4.2)
    • C12Y402/03—Carbon-oxygen lyases (4.2) acting on phosphates (4.2.3)
    • C12Y402/03001—Threonine synthase (4.2.3.1)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y403/00—Carbon-nitrogen lyases (4.3)
    • C12Y403/01—Ammonia-lyases (4.3.1)
    • C12Y403/01019—Threonine ammonia-lyase (4.3.1.19)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y504/00—Intramolecular transferases (5.4)
    • C12Y504/99—Intramolecular transferases (5.4) transferring other groups (5.4.99)
    • C12Y504/99002—Methylmalonyl-CoA mutase (5.4.99.2)
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Biotechnology (AREA)
  • Biomedical Technology (AREA)
  • Microbiology (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Biophysics (AREA)
  • Plant Pathology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Virology (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
CA2848253A 2010-09-15 2012-03-08 Production of odd chain fatty acid derivatives in recombinant microbial cells Active CA2848253C (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US38308610P 2010-09-15 2010-09-15
US13/232,927 2011-09-14
US13/232,927 US8372610B2 (en) 2010-09-15 2011-09-14 Production of odd chain fatty acid derivatives in recombinant microbial cells
PCT/US2012/028256 WO2013039563A1 (en) 2010-09-15 2012-03-08 Production of odd chain fatty acid derivatives in recombinant microbial cells

Publications (2)

Publication Number Publication Date
CA2848253A1 CA2848253A1 (en) 2013-03-21
CA2848253C true CA2848253C (en) 2020-11-03

Family

ID=47884064

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2848253A Active CA2848253C (en) 2010-09-15 2012-03-08 Production of odd chain fatty acid derivatives in recombinant microbial cells

Country Status (7)

Country Link
US (3) US8372610B2 (enExample)
EP (2) EP2756090B1 (enExample)
JP (1) JP6141282B2 (enExample)
CN (1) CN103906845B (enExample)
CA (1) CA2848253C (enExample)
MY (1) MY191370A (enExample)
WO (1) WO2013039563A1 (enExample)

Families Citing this family (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA3101888A1 (en) 2008-05-16 2009-11-19 REG Life Sciences, LLC Methods and compositions for producing hydrocarbons
CN105154380B (zh) 2008-10-28 2018-11-09 Reg生命科学有限责任公司 用于产生脂肪醇的方法和组合物
US9957534B2 (en) 2008-11-06 2018-05-01 Kiverdi, Inc. Engineered CO2-fixing chemotrophic microorganisms producing carbon-based products and methods of using the same
WO2013148348A1 (en) * 2012-03-28 2013-10-03 Kiverdi, Inc. Engineered co2-fixing chemotrophic microorganisms producing carbon-based products and methods of using the same
CA2775390C (en) 2009-09-27 2021-06-29 Opx Biotechnologies, Inc. Method for producing 3-hydroxypropionic acid and other products
CA2883968C (en) * 2012-04-02 2022-08-23 REG Life Sciences, LLC Improved production of fatty acid derivatives
CN109182238A (zh) 2012-08-10 2019-01-11 嘉吉有限公司 用于生产脂肪酸和脂肪酸衍生产物的微生物及方法
WO2014093505A2 (en) 2012-12-12 2014-06-19 Ls9, Inc. Acp-mediated production of fatty acid derivatives
US20140193867A1 (en) * 2012-12-21 2014-07-10 William Marsh Rice University Microbial odd chain fatty acids
WO2014113571A2 (en) 2013-01-16 2014-07-24 Ls9, Inc. Acyl-acp reductase with improved properties
US20140255330A1 (en) 2013-03-05 2014-09-11 The Procter & Gamble Company Mixed Sugar Compositions
WO2014146026A1 (en) 2013-03-15 2014-09-18 Opx Biotechnologies, Inc. Bioproduction of chemicals
MY203897A (en) 2013-06-14 2024-07-23 Genomatica Inc Methods of producing omega-hydroxylated fatty acid derivatives
JP6603658B2 (ja) * 2013-07-19 2019-11-06 カーギル インコーポレイテッド 脂肪酸及び脂肪酸誘導体の製造のための微生物及び方法
US11408013B2 (en) 2013-07-19 2022-08-09 Cargill, Incorporated Microorganisms and methods for the production of fatty acids and fatty acid derived products
US9469586B2 (en) 2013-08-19 2016-10-18 REG Life Sciences, LLC Production of partially refined waste glycerol
EP3019461A1 (en) 2013-08-19 2016-05-18 REG Life Sciences, LLC Production of partially refined waste glycerol
ES2631807T3 (es) 2013-09-13 2017-09-05 REG Life Sciences, LLC Variantes de acetil-CoA carboxilasa mejoradas
WO2015077752A1 (en) 2013-11-25 2015-05-28 Genomatica, Inc. Methods for enhancing microbial production of specific length fatty alcohols in the presence of methanol
BR112016012371B1 (pt) 2013-12-05 2023-03-28 Genomatica, Inc Célula bacteriana recombinante para a produção de uma amina graxa, cultura de células e método de produção de uma amina graxa
WO2015089127A1 (en) * 2013-12-12 2015-06-18 Dow Global Technologies Llc Processes to prepare elongated 2-ketoacids and c6-c10 compounds therefrom via genetic modifications to microbial metabolic pathways
CN106164282A (zh) * 2014-04-10 2016-11-23 Reg生命科学有限责任公司 有机化合物的半合成途径
US11441130B2 (en) 2014-06-16 2022-09-13 Genomatica, Inc. Omega-hydroxylase-related fusion polypeptides with improved properties
US9938543B2 (en) * 2014-06-16 2018-04-10 Invista North America S.A.R.L. Methods, reagents and cells for biosynthesizing glutarate methyl ester
BR112017001105A2 (pt) 2014-07-18 2018-07-24 REG Life Sciences, LLC produção microbiana de dióis graxos
EP2993228B1 (en) 2014-09-02 2019-10-09 Cargill, Incorporated Production of fatty acid esters
CA2969842C (en) 2014-12-10 2023-08-22 Dow Global Technologies Llc Genetically modified phenylpyruvate decarboxylase, processes to prepare, and uses thereof
WO2016137897A1 (en) * 2015-02-24 2016-09-01 William Marsh Rice University Kasiii-free fa synthesis
JP6681625B2 (ja) * 2015-06-16 2020-04-15 国立大学法人名古屋大学 タンパク質の発現方法
WO2017101987A1 (en) 2015-12-15 2017-06-22 REG Life Sciences, LLC Omega-hydroxylase-related fusion polypeptide variants with improved properties
CN106916856B (zh) * 2015-12-28 2021-08-24 丰益(上海)生物技术研发中心有限公司 提高产脂微生物生产奇数碳脂肪酸产量的培养基及方法
CN114773160B (zh) 2016-09-14 2025-03-07 基因组股份公司 1,3-脂肪二醇化合物和其衍生物
EP3519579B1 (en) 2016-09-30 2025-11-05 Dow Global Technologies LLC Processes to prepare elongated 2-ketoacids and c-5-c10 compounds therefrom via genetic modifications to microbial metabolic pathways
WO2018144701A2 (en) 2017-02-02 2018-08-09 Cargill Incorporated Genetically modified cells that produce c6-c10 fatty acid derivatives
CN111094558A (zh) 2017-04-03 2020-05-01 基因组股份公司 对产生中链脂肪酸衍生物具有改善的活性的硫酯酶变体
WO2019056071A1 (en) * 2017-09-21 2019-03-28 The University Of Queensland RECOMBINANT MICROORGANISMS
EP3688175B1 (en) 2017-09-29 2024-03-13 Dow Global Technologies LLC Genetically modified isopropylmalate isomerase enzyme complexes and processes to prepare elongated 2-ketoacids and c5-c10 compounds therewith
US12098168B2 (en) 2018-08-31 2024-09-24 Genomatica, Inc. XylR mutant for improved xylose utilization or improved co-utilization of glucose and xylose preliminary
US12492416B2 (en) * 2018-10-04 2025-12-09 Anna University Production of L-2-aminobutyrate from citramalate, citraconate or 2-oxobutanoate
CN109517811B (zh) * 2018-11-29 2022-11-11 滨州医学院 一种β-酮脂酰-ACP合成酶突变体
CN110129400B (zh) * 2019-05-25 2023-09-01 华南理工大学 一种提高微生物油脂奇数碳链脂肪酸含量的方法
CN112941096B (zh) * 2019-12-10 2023-05-26 北京化工大学 重组质粒组合、基因改造酵母菌及生产奇数链脂肪酸方法
WO2023178197A1 (en) 2022-03-16 2023-09-21 Genomatica, Inc. Recombinant microbes for production of trans-2 unsaturated fatty acids and derivatives thereof

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU7791991A (en) 1990-04-24 1991-11-11 Stratagene Methods for phenotype creation from multiple gene populations
US6428767B1 (en) 1995-05-12 2002-08-06 E. I. Du Pont De Nemours And Company Method for identifying the source of carbon in 1,3-propanediol
WO2008119082A2 (en) 2007-03-28 2008-10-02 Ls9, Inc. Enhanced production of fatty acid derivatives
CN101490241A (zh) * 2006-05-19 2009-07-22 Ls9公司 脂肪酸及其衍生物的制备
US8110670B2 (en) * 2006-05-19 2012-02-07 Ls9, Inc. Enhanced production of fatty acid derivatives
ES2528482T3 (es) 2006-05-19 2015-02-10 Ls9, Inc. Producción de ácidos grasos y derivados de los mismos
WO2008098227A2 (en) * 2007-02-09 2008-08-14 The Regents Of The University Of California Biofuel production by recombinant microorganisms
US9695426B2 (en) 2007-02-09 2017-07-04 The Regents Of The University Of California Biofuel production by recombinant microorganisms
KR101862691B1 (ko) 2007-05-22 2018-05-31 알이지 라이프 사이언시스, 엘엘씨 탄화수소-생산 유전자와 이들의 이용 방법
MX2010005061A (es) * 2007-11-10 2010-09-09 Joule Unltd Inc Organismos hiperfotosinteticos.
US8183028B2 (en) 2007-12-21 2012-05-22 Ls9, Inc. Methods and compositions for producing olefins
CA3101888A1 (en) 2008-05-16 2009-11-19 REG Life Sciences, LLC Methods and compositions for producing hydrocarbons
US8097439B2 (en) 2008-10-07 2012-01-17 Ls9, Inc. Methods and compositions for producing fatty aldehydes
CN105154380B (zh) 2008-10-28 2018-11-09 Reg生命科学有限责任公司 用于产生脂肪醇的方法和组合物
CA2747516C (en) * 2008-12-23 2019-11-05 Ls9, Inc. Methods and compositions related to thioesterase enzymes
BRPI1010920B1 (pt) * 2009-05-22 2020-04-28 Codexis Inc processo para a produção biológica de álcoois graxos
US8715971B2 (en) 2009-09-09 2014-05-06 Genomatica, Inc. Microorganisms and methods for the co-production of isopropanol and 1,4-butanediol
US8933131B2 (en) 2010-01-12 2015-01-13 The Procter & Gamble Company Intermediates and surfactants useful in household cleaning and personal care compositions, and methods of making the same

Also Published As

Publication number Publication date
EP3957736C0 (en) 2025-08-06
EP2756090B1 (en) 2021-08-04
JP2014526262A (ja) 2014-10-06
CN103906845B (zh) 2017-09-29
US8372610B2 (en) 2013-02-12
US20210324431A1 (en) 2021-10-21
CN103906845A (zh) 2014-07-02
EP3957736A1 (en) 2022-02-23
MY191370A (en) 2022-06-20
US20120070868A1 (en) 2012-03-22
EP3957736B1 (en) 2025-08-06
EP2756090A1 (en) 2014-07-23
JP6141282B2 (ja) 2017-06-07
WO2013039563A1 (en) 2013-03-21
US20150167033A1 (en) 2015-06-18
CA2848253A1 (en) 2013-03-21

Similar Documents

Publication Publication Date Title
US20210324431A1 (en) Production Of Odd Chain Fatty Acid Derivatives In Recombinant Microbial Cells
US20240150774A1 (en) Production of fatty acid derivatives
US8530221B2 (en) Production of branched chain fatty acids and derivatives thereof in recombinant microbial cells
US20210309979A1 (en) Enzyme Variants With Improved Ester Synthase Properties
CA2738938C (en) Methods and compositions for producing fatty aldehydes
EP2663636B1 (en) Production of branched chain fatty acids and derivatives thereof in recombinant microbial cells
US20140215904A1 (en) Compositions comprising and methods for producing beta-hydroxy fatty acid esters
JP2022043100A (ja) 組換え微生物細胞における奇数鎖脂肪酸誘導体の生成

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20170307

H11 Ip right ceased following rejected request for revival

Free format text: ST27 STATUS EVENT CODE: T-6-6-H10-H11-H101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: TIME LIMIT FOR REVERSAL EXPIRED

Effective date: 20250909

H13 Ip right lapsed

Free format text: ST27 STATUS EVENT CODE: N-4-6-H10-H13-H100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE AND LATE FEE NOT PAID BY DEADLINE OF NOTICE

Effective date: 20251106