WO2010144746A2 - Microorganisms and methods for carbon-efficient biosynthesis of mek and 2-butanol - Google Patents

Microorganisms and methods for carbon-efficient biosynthesis of mek and 2-butanol Download PDF

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Publication number
WO2010144746A2
WO2010144746A2 PCT/US2010/038230 US2010038230W WO2010144746A2 WO 2010144746 A2 WO2010144746 A2 WO 2010144746A2 US 2010038230 W US2010038230 W US 2010038230W WO 2010144746 A2 WO2010144746 A2 WO 2010144746A2
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WIPO (PCT)
Prior art keywords
mek
microbial organism
akp
encoded
group
Prior art date
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Ceased
Application number
PCT/US2010/038230
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English (en)
French (fr)
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WO2010144746A3 (en
Inventor
Robin E. Osterhout
Wei Niu
Anthony P. Burgard
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Genomatica Inc
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Genomatica Inc
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Priority to EP10786874.7A priority Critical patent/EP2440669A4/en
Priority to JP2012515163A priority patent/JP2012529889A/ja
Publication of WO2010144746A2 publication Critical patent/WO2010144746A2/en
Publication of WO2010144746A3 publication Critical patent/WO2010144746A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
    • C12P7/26—Ketones
    • 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
    • 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
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
    • C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
    • C12P7/16—Butanols
    • 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

Definitions

  • non-naturally occurring when used in reference to a microbial organism or microorganism of the invention is intended to mean that the microbial organism has at least one genetic alteration not normally found in a naturally occurring strain of the referenced species, including wild-type strains of the referenced species.
  • Genetic alterations include, for example, modifications introducing expressible nucleic acids encoding metabolic polypeptides, other nucleic acid additions, nucleic acid deletions and/or other functional disruption of the microbial genetic material. Such modifications include, for example, coding regions and functional fragments thereof, for heterologous, homologous or both heterologous and homologous polypeptides for the referenced species. Additional modifications include, for example, non-coding regulatory regions in which the modifications alter expression of a gene or operon.
  • Exemplary metabolic polypeptides include enzymes or proteins within a MEK or 2- butanol biosynthetic pathway.
  • ortholog is a gene or genes that are related by vertical descent and are responsible for substantially the same or identical functions in different organisms.
  • mouse epoxide hydrolase and human epoxide hydrolase can be considered orthologs for the biological function of hydrolysis of epoxides.
  • Genes are related by vertical descent when, for example, they share sequence similarity of sufficient amount to indicate they are homologous, or related by evolution from a common ancestor.
  • Genes can also be considered orthologs if they share three-dimensional structure but not necessarily sequence similarity, of a sufficient amount to indicate that they have evolved from a common ancestor to the extent that the primary sequence similarity is not identifiable.
  • Genes that are orthologous can encode proteins with sequence similarity of about 25% to 100% amino acid sequence identity.
  • the non- naturally occurring microbial organism comprises at least one exogenous nucleic acid encoding an enzyme or protein that converts a substrate to a product selected from the group consisting of alanine to AKP, AKP to 4-aminobutan-2-one, 4-aminobutan-2-one to butenone, butenone to MEK, and MEK to 2-butanol.
  • the invention provides a non-naturally occurring microbial organism containing at least one exogenous nucleic acid encoding an enzyme or protein, where the enzyme or protein converts the substrates and products of a MEK or 2-butanol pathway, such as that shown in Figure 2.
  • malonyl-CoA reductase which transforms malonyl-CoA to malonic semialdehyde.
  • Malonyl-CoA reductase is a key enzyme in autotrophic carbon fixation via the 3-hydroxypropionate cycle in thermoacidophilic archaeal bacteria (Berg et al., Science 318:1782-1786 (2007); Thauer, R.K., Science 318:1732-1733 (2007)).
  • the enzyme utilizes NADPH as a cofactor and has been characterized in Metallosphaera and Sulfolobus spp (Alber et al., J. Bacteriol.
  • 2-(Hydroxymethyl)glutarate dehydratase is a [4Fe-4S]-containing enzyme that dehydrates 2- (hydroxymethyl)glutarate to 2-methylene-glutarate, studied for its role in nicontinate catabolism in Eubacterium barken (formerly Clostridium barkeri) (Alhapel et al., Proc. Natl. Acad. Sci. USA 103:12341-12346 (2006)). Similar enzymes with high sequence homology are found in Bacteroides capillosus, Anaerotruncus colihominis, and Natranaerobius thermophilius.
  • Indolepyruvate decarboxylase is an enzyme that catalyzes the decarboxylation of indolepyruvate to indoleacetaldehyde in plants and plant bacteria.
  • Synthesis gas also known as syngas or producer gas
  • syngas is the major product of gasification of coal and of carbonaceous materials such as biomass materials, including agricultural crops and residues.
  • Syngas is a mixture primarily of H 2 and CO and can be obtained from the gasification of any organic feedstock, including but not limited to coal, coal oil, natural gas, biomass, and waste organic matter. Gasification is generally carried out under a high fuel to oxygen ratio. Although largely H 2 and CO, syngas can also include CO 2 and other gases in smaller quantities.
  • synthesis gas provides a cost effective source of gaseous carbon such as CO and, additionally, CO 2 .
  • Homologous fragments are hybridized in the absence of polymerase to a complementary ssDNA scaffold. Any overlapping unhybridized fragment ends are trimmed down by an exonuclease. Gaps between fragments are filled in, and then ligated to give a pool of full- length diverse strands hybridized to the scaffold (that contains U to preclude amplification). The scaffold then is destroyed and is replaced by a new strand complementary to the diverse strand by PCR amplification. The method involves one strand (scaffold) that is from only one parent while the priming fragments derive from other genes; the parent scaffold is selected against. Thus, no reannealing with parental fragments occurs. Overlapping fragments are trimmed with an exonuclease.
  • Nucleotide Exchange and Excision Technology NexT exploits a combination of dUTP incorporation followed by treatment with uracil DNA glycosylase and then piperidine to perform endpoint DNA fragmentation.
  • the gene is reassembled using internal PCR primer extension with proofreading polymerase.
  • the sizes for shuffling are directly controllable using varying dUPT::dTTP ratios. This is an end point reaction using simple methods for uracil incorporation and cleavage.
  • One can use other nucleotide analogs such as 8-oxo-guanine with this method. Additionally, the technique works well with very short fragments (86 bp) and has a low error rate. Chemical cleavage of DNA means very few unshuffled clones.
  • CP450 this produced mammalian activity in a more soluble enzyme.
  • GSSM Gene Site Saturation Mutagenesis
  • the starting materials are a supercoiled dsDNA plasmid with insert and 2 primers degenerate at the desired site for mutations.
  • Primers carry the mutation of interest and anneal to the same sequence on opposite strands of DNA; mutation in the middle of the primer and -20 nucleotides of correct sequence flanking on each side.
  • An in silico stoichiometric model of E. coli metabolism can be employed to identify essential genes for metabolic pathways as exemplified previously and described in, for example, U.S. patent publications US 2002/0012939, US 2003/0224363, US 2004/0029149, US 2004/0072723, US 2003/0059792, US 2002/0168654 and US 2004/0009466, and in U.S. Patent No. 7,127,379.
  • the OptKnock mathematical framework can be applied to pinpoint gene deletions leading to the growth-coupled production of a desired product. Further, the solution of the bilevel OptKnock problem provides only one set of deletions.
  • the growth rate is determined by measuring optical density using a spectrophotometer (600 nm), and the glucose uptake rate by monitoring carbon source depletion over time.
  • Byproducts such as undesirable alcohols, organic acids, and residual glucose can be quantified by HPLC (Shimadzu) with an HPX-087 column (BioRad), using a refractive index detector for glucose and alcohols, and a UV detector for organic acids (Lin et al., Biotechnol. Bioeng. 90:775-779 (2005)).

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  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biotechnology (AREA)
  • General Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • General Health & Medical Sciences (AREA)
  • Biomedical Technology (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Plant Pathology (AREA)
  • Biophysics (AREA)
  • Physics & Mathematics (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
PCT/US2010/038230 2009-06-10 2010-06-10 Microorganisms and methods for carbon-efficient biosynthesis of mek and 2-butanol Ceased WO2010144746A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP10786874.7A EP2440669A4 (en) 2009-06-10 2010-06-10 MICROOGANISMS AND PROCEDURES FOR THE CARBON EFFECTIVE BIOSYNTHESIS MEK AND 2-BUTANOL
JP2012515163A JP2012529889A (ja) 2009-06-10 2010-06-10 Ｍｅｋ及び２−ブタノールの炭素効率のよい生合成のための微生物及び方法

Applications Claiming Priority (4)

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US18596909P 2009-06-10 2009-06-10
US61/185,969 2009-06-10
US18723809P 2009-06-15 2009-06-15
US61/187,238 2009-06-15

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WO2010144746A2 true WO2010144746A2 (en) 2010-12-16
WO2010144746A3 WO2010144746A3 (en) 2011-02-24

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EP (1) EP2440669A4 (enExample)
JP (1) JP2012529889A (enExample)
WO (1) WO2010144746A2 (enExample)

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CN103214042A (zh) * 2013-04-27 2013-07-24 中国科学院金属研究所 一种超顺磁稀土金属间化合物纳米颗粒及其制备方法
WO2013173711A1 (en) 2012-05-18 2013-11-21 Novozymes A/S Bacterial mutants with improved transformation efficiency
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WO2014152434A2 (en) 2013-03-15 2014-09-25 Genomatica, Inc. Microorganisms and methods for producing butadiene and related compounds by formate assimilation
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WO2015084633A1 (en) 2013-12-03 2015-06-11 Genomatica, Inc. Microorganisms and methods for improving product yields on methanol using acetyl-coa synthesis
EP2529011A4 (en) * 2010-01-29 2015-07-15 Genomatica Inc MICROORGANISMS AND METHODS FOR BIOSYNTHESIS OF P-TOLUATE AND TEREPHTHALATE
WO2016044713A1 (en) 2014-09-18 2016-03-24 Genomatica, Inc. Non-natural microbial organisms with improved energetic efficiency
WO2019152375A1 (en) 2018-01-30 2019-08-08 Genomatica, Inc. Fermentation systems and methods with substantially uniform volumetric uptake rate of a reactive gaseous component
US10597684B2 (en) 2013-12-27 2020-03-24 Genomatica, Inc. Methods and organisms with increased carbon flux efficiencies

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EP2304039B1 (en) 2008-06-17 2019-08-21 Genomatica, Inc. Microorganisms and methods for the biosynthesis of fumarate, malate, and acrylate
KR20110097951A (ko) 2008-12-16 2011-08-31 게노마티카 인코포레이티드 합성가스와 다른 탄소원을 유용 제품으로 전환시키기 위한 미생물 및 방법
CA2783096A1 (en) 2009-12-10 2011-06-16 Genomatica, Inc. Methods and organisms for converting synthesis gas or other gaseous carbon sources and methanol to 1,3-butanediol
US8445244B2 (en) * 2010-02-23 2013-05-21 Genomatica, Inc. Methods for increasing product yields
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