CA2722680A1 - Microorganisms for the production of methacrylic acid - Google Patents
Microorganisms for the production of methacrylic acid Download PDFInfo
- Publication number
- CA2722680A1 CA2722680A1 CA2722680A CA2722680A CA2722680A1 CA 2722680 A1 CA2722680 A1 CA 2722680A1 CA 2722680 A CA2722680 A CA 2722680A CA 2722680 A CA2722680 A CA 2722680A CA 2722680 A1 CA2722680 A1 CA 2722680A1
- Authority
- CA
- Canada
- Prior art keywords
- coa
- microbial organism
- naturally occurring
- exogenous nucleic
- methacrylic acid
- 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.)
- Abandoned
Links
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims abstract description 570
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 146
- 244000005700 microbiome Species 0.000 title description 27
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- 150000007523 nucleic acids Chemical class 0.000 claims abstract description 307
- 108020004707 nucleic acids Proteins 0.000 claims abstract description 300
- 102000039446 nucleic acids Human genes 0.000 claims abstract description 300
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 claims abstract description 245
- DBXBTMSZEOQQDU-UHFFFAOYSA-N 3-hydroxyisobutyric acid Chemical compound OCC(C)C(O)=O DBXBTMSZEOQQDU-UHFFFAOYSA-N 0.000 claims abstract description 202
- 238000000034 method Methods 0.000 claims abstract description 195
- 238000012258 culturing Methods 0.000 claims abstract description 37
- 108090000623 proteins and genes Proteins 0.000 claims description 247
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- 230000012010 growth Effects 0.000 claims description 76
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- 229920001791 ((R)-3-Hydroxybutanoyl)(n-2) Polymers 0.000 claims description 61
- QHHKKMYHDBRONY-RMNRSTNRSA-N 3-hydroxybutanoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC(O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 QHHKKMYHDBRONY-RMNRSTNRSA-N 0.000 claims description 61
- BAMBWCGEVIAQBF-CITAKDKDSA-N 4-hydroxybutyryl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCO)O[C@H]1N1C2=NC=NC(N)=C2N=C1 BAMBWCGEVIAQBF-CITAKDKDSA-N 0.000 claims description 61
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- MZFOKIKEPGUZEN-FBMOWMAESA-N methylmalonyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C(C(O)=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MZFOKIKEPGUZEN-FBMOWMAESA-N 0.000 claims description 42
- FFVUICCDNWZCRC-ZSJPKINUSA-N 2-hydroxyisobutanoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C(C)(C)O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 FFVUICCDNWZCRC-ZSJPKINUSA-N 0.000 claims description 41
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- UATIGEHITDTAGF-CITAKDKDSA-N vinylacetyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC=C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 UATIGEHITDTAGF-CITAKDKDSA-N 0.000 claims description 23
- 108010077268 3-hydroxyisobutyryl-CoA hydrolase Proteins 0.000 claims description 21
- 102100034767 3-hydroxyisobutyryl-CoA hydrolase, mitochondrial Human genes 0.000 claims description 21
- KPGXRSRHYNQIFN-UHFFFAOYSA-L 2-oxoglutarate(2-) Chemical compound [O-]C(=O)CCC(=O)C([O-])=O KPGXRSRHYNQIFN-UHFFFAOYSA-L 0.000 claims description 20
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- NPYQJIHHTGFBLN-UHFFFAOYSA-N 3-methylmalic acid Chemical compound OC(=O)C(C)C(O)C(O)=O NPYQJIHHTGFBLN-UHFFFAOYSA-N 0.000 claims description 13
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- VNAIXPVBNZGXNO-UHFFFAOYSA-N 3-amino-2-methylpropanoic acid azane Chemical compound N.NCC(C(=O)O)C VNAIXPVBNZGXNO-UHFFFAOYSA-N 0.000 claims description 11
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- GXSDWXSYZHGBBO-RXMQYKEDSA-N (2r)-2-amino-2-hydroxypentanedioic acid Chemical compound OC(=O)[C@@](O)(N)CCC(O)=O GXSDWXSYZHGBBO-RXMQYKEDSA-N 0.000 claims description 6
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Classifications
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- 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
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/42—Hydroxy-carboxylic acids
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- 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)
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- C12N9/10—Transferases (2.)
- C12N9/1096—Transferases (2.) transferring nitrogenous groups (2.6)
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- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/88—Lyases (4.)
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/90—Isomerases (5.)
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- 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
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
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- 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)
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
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- C12Y—ENZYMES
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
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| PCT/US2009/042426 WO2009135074A2 (en) | 2008-05-01 | 2009-04-30 | Microorganisms for the production of methacrylic acid |
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| DE102006025821A1 (de) | 2006-06-02 | 2007-12-06 | Degussa Gmbh | Ein Enzym zur Herstellung von Mehylmalonatsemialdehyd oder Malonatsemialdehyd |
| JP2011519561A (ja) | 2008-05-01 | 2011-07-14 | ジェノマティカ， インコーポレイテッド | メタクリル酸の産生のための微生物 |
| US8129154B2 (en) | 2008-06-17 | 2012-03-06 | Genomatica, Inc. | Microorganisms and methods for the biosynthesis of fumarate, malate, and acrylate |
| CA2735883C (en) | 2008-09-10 | 2020-05-05 | Genomatica, Inc. | Microorganisms for the production of 1,4-butanediol |
| US20100184173A1 (en) * | 2008-11-14 | 2010-07-22 | Genomatica, Inc. | Microorganisms for the production of methyl ethyl ketone and 2-butanol |
| US9637746B2 (en) | 2008-12-15 | 2017-05-02 | Greenlight Biosciences, Inc. | Methods for control of flux in metabolic pathways |
| KR20110097951A (ko) | 2008-12-16 | 2011-08-31 | 게노마티카 인코포레이티드 | 합성가스와 다른 탄소원을 유용 제품으로 전환시키기 위한 미생물 및 방법 |
| EP2379728A4 (en) * | 2008-12-22 | 2016-04-13 | Greenlight Biosciences Inc | COMPOSITIONS AND METHODS FOR THE PRODUCTION OF A COMPOUND |
| US9454640B2 (en) * | 2009-02-26 | 2016-09-27 | Intrexon Ceu, Inc. | Mammalian cell line models and related methods |
| LT2438036T (lt) | 2009-06-04 | 2017-06-26 | Genomatica, Inc. | Fermentacijos sultinio komponentų išskyrimo būdas |
| SI3392340T1 (sl) | 2009-06-04 | 2022-05-31 | Genomatica, Inc. | Mikroorganizmi za proizvodnjo 1,4-BUTANDIOLA in pripadajoči postopki |
| JP2012529889A (ja) | 2009-06-10 | 2012-11-29 | ゲノマチカ， インク． | 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 |
| AU2010306785B2 (en) | 2009-10-13 | 2016-01-14 | Genomatica, Inc. | Microorganisms for the production of 1,4-butanediol, 4-hydroxybutanal, 4-hydroxybutyryl-CoA, putrescine and related compounds, and methods related thereto |
| US8530210B2 (en) | 2009-11-25 | 2013-09-10 | Genomatica, Inc. | Microorganisms and methods for the coproduction 1,4-butanediol and gamma-butyrolactone |
| CN109136161A (zh) | 2009-12-10 | 2019-01-04 | 基因组股份公司 | 合成气或其他气态碳源和甲醇转化为1,3-丁二醇的方法和有机体 |
| US8637286B2 (en) | 2010-02-23 | 2014-01-28 | Genomatica, Inc. | Methods for increasing product yields |
| MX336229B (es) | 2010-05-05 | 2016-01-08 | Genomatica Inc | Microorganismos y metodos para la biosintesis de butadieno. |
| WO2011140516A2 (en) | 2010-05-07 | 2011-11-10 | Greenlight Biosciences, Inc. | Methods for control of flux in metabolic pathways through enzyme relocation |
| WO2012030980A1 (en) | 2010-08-31 | 2012-03-08 | Greenlight Biosciences, Inc. | Methods for control of flux in metabolic pathways through protease manipulation |
| RU2013148813A (ru) * | 2011-04-01 | 2015-06-10 | Дженоматика, Инк. | Микроорганизмы для получения метакриловой кислоты и сложные эфиры метакриловой кислоты и относящиеся к ним способы |
| US20120330560A1 (en) * | 2011-06-23 | 2012-12-27 | Ramot At Tel-Aviv University Ltd. | Method and system for predicting pertubations altering metabolic states |
| SG2014012520A (en) | 2011-07-12 | 2014-06-27 | Scientist Of Fortune Sa | Recombinant microorganism for the production of useful metabolites |
| MY165731A (en) | 2011-07-29 | 2018-04-20 | Mitsui Chemicals Inc | Microorganism having carbon dioxide fixation cycle introduced thereinto |
| SG2014014377A (en) | 2011-09-09 | 2014-05-29 | Greenlight Biosciences Inc | Cell-free preparation of carbapenems |
| US8940509B2 (en) | 2011-11-02 | 2015-01-27 | Genomatica, Inc. | Microorganisms and methods for the production of caprolactone |
| DE102012207921A1 (de) | 2012-05-11 | 2013-11-14 | Evonik Industries Ag | Mehrstufiges Syntheseverfahren mit Synthesegas |
| US9803209B2 (en) | 2012-05-18 | 2017-10-31 | Novozymes A/S | Bacterial mutants with improved transformation efficiency |
| EP3831951A3 (en) | 2012-06-04 | 2021-09-15 | Genomatica, Inc. | Microorganisms and methods for production of 4-hydroxybutyrate, 1,4-butanediol and related compounds |
| EP2674489A1 (en) * | 2012-06-15 | 2013-12-18 | Evonik Industries AG | Biotechnological 2-hydroxyisobutyric acid production |
| AU2013314153B2 (en) * | 2012-09-10 | 2016-05-12 | Mitsubishi Chemical Corporation | Method for producing methacrylic acid and/or ester thereof |
| ES2689477T3 (es) | 2012-09-10 | 2018-11-14 | Mitsubishi Chemical Corporation | Método para producir éster del ácido metacrílico |
| WO2014052630A1 (en) | 2012-09-27 | 2014-04-03 | Novozymes, Inc. | Bacterial mutants with improved transformation efficiency |
| EP2935598A1 (en) | 2012-12-21 | 2015-10-28 | Greenlight Biosciences Inc. | Cell-free system for converting methane into fuel, pyruvate or isobutanol |
| BE1021047B1 (fr) * | 2013-01-18 | 2015-02-25 | Man To Tree S.A. | Actinobacillus succinogenes genetiquement modifiee et son utilisation pour la production d'acide succinique |
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-
2009
- 2009-04-30 JP JP2011507667A patent/JP2011519561A/ja active Pending
- 2009-04-30 EP EP09739876A patent/EP2285973A4/en not_active Ceased
- 2009-04-30 BR BRPI0911759A patent/BRPI0911759A2/pt not_active IP Right Cessation
- 2009-04-30 AU AU2009242615A patent/AU2009242615A1/en not_active Abandoned
- 2009-04-30 CA CA2722680A patent/CA2722680A1/en not_active Abandoned
- 2009-04-30 US US12/433,829 patent/US8241877B2/en not_active Expired - Fee Related
- 2009-04-30 WO PCT/US2009/042426 patent/WO2009135074A2/en not_active Ceased
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2012
- 2012-06-22 US US13/531,377 patent/US8900837B2/en active Active
- 2012-07-10 US US13/545,880 patent/US8865439B2/en active Active
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2014
- 2014-05-27 JP JP2014108853A patent/JP2014147400A/ja active Pending
- 2014-12-01 US US14/557,188 patent/US9951355B2/en active Active
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2018
- 2018-04-23 US US15/960,252 patent/US20190376096A1/en not_active Abandoned
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- 2020-08-19 US US16/997,704 patent/US20210040511A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20090275096A1 (en) | 2009-11-05 |
| EP2285973A2 (en) | 2011-02-23 |
| US20160208293A1 (en) | 2016-07-21 |
| BRPI0911759A2 (pt) | 2019-09-24 |
| EP2285973A4 (en) | 2012-04-25 |
| US20190376096A1 (en) | 2019-12-12 |
| WO2009135074A3 (en) | 2009-12-30 |
| JP2011519561A (ja) | 2011-07-14 |
| AU2009242615A1 (en) | 2009-11-05 |
| US8241877B2 (en) | 2012-08-14 |
| US20120276604A1 (en) | 2012-11-01 |
| WO2009135074A2 (en) | 2009-11-05 |
| JP2014147400A (ja) | 2014-08-21 |
| US8865439B2 (en) | 2014-10-21 |
| US9951355B2 (en) | 2018-04-24 |
| US20210040511A1 (en) | 2021-02-11 |
| US8900837B2 (en) | 2014-12-02 |
| US20120276605A1 (en) | 2012-11-01 |
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