JP2012506716A5 - - Google Patents
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- JP2012506716A5 JP2012506716A5 JP2011534730A JP2011534730A JP2012506716A5 JP 2012506716 A5 JP2012506716 A5 JP 2012506716A5 JP 2011534730 A JP2011534730 A JP 2011534730A JP 2011534730 A JP2011534730 A JP 2011534730A JP 2012506716 A5 JP2012506716 A5 JP 2012506716A5
- Authority
- JP
- Japan
- Prior art keywords
- conversion
- gene
- involved
- exogenous
- dihydroxyacetone
- 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.)
- Pending
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- 108090000623 proteins and genes Proteins 0.000 claims description 202
- 238000006243 chemical reaction Methods 0.000 claims description 165
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 87
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 66
- GNGACRATGGDKBX-UHFFFAOYSA-N dihydroxyacetone phosphate Chemical compound OCC(=O)COP(O)(O)=O GNGACRATGGDKBX-UHFFFAOYSA-N 0.000 claims description 58
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 53
- 108090000790 Enzymes Proteins 0.000 claims description 50
- 102000004190 Enzymes Human genes 0.000 claims description 50
- ZSLZBFCDCINBPY-ZSJPKINUSA-N acetyl-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)O[C@H]1N1C2=NC=NC(N)=C2N=C1 ZSLZBFCDCINBPY-ZSJPKINUSA-N 0.000 claims description 50
- 230000006378 damage Effects 0.000 claims description 46
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims description 40
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 38
- 230000002018 overexpression Effects 0.000 claims description 34
- 229940120503 dihydroxyacetone Drugs 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 24
- 239000000047 product Substances 0.000 claims description 21
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 claims description 20
- 244000005700 microbiome Species 0.000 claims description 20
- 239000004310 lactic acid Substances 0.000 claims description 19
- 235000014655 lactic acid Nutrition 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 19
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 16
- KHPXUQMNIQBQEV-UHFFFAOYSA-N oxaloacetic acid Chemical compound OC(=O)CC(=O)C(O)=O KHPXUQMNIQBQEV-UHFFFAOYSA-N 0.000 claims description 16
- 229930029653 phosphoenolpyruvate Natural products 0.000 claims description 16
- DTBNBXWJWCWCIK-UHFFFAOYSA-N phosphoenolpyruvic acid Chemical compound OC(=O)C(=C)OP(O)(O)=O DTBNBXWJWCWCIK-UHFFFAOYSA-N 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 claims description 14
- 239000006227 byproduct Substances 0.000 claims description 12
- 235000019260 propionic acid Nutrition 0.000 claims description 12
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 12
- 239000002207 metabolite Substances 0.000 claims description 11
- LIPOUNRJVLNBCD-UHFFFAOYSA-N acetyl dihydrogen phosphate Chemical compound CC(=O)OP(O)(O)=O LIPOUNRJVLNBCD-UHFFFAOYSA-N 0.000 claims description 10
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 10
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 9
- 235000004279 alanine Nutrition 0.000 claims description 9
- 241000894006 Bacteria Species 0.000 claims description 8
- 241000588724 Escherichia coli Species 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 230000007935 neutral effect Effects 0.000 claims description 8
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 claims description 8
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 claims description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 235000019441 ethanol Nutrition 0.000 claims description 6
- 239000001530 fumaric acid Substances 0.000 claims description 6
- 101150033931 gldA gene Proteins 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 101150060030 poxB gene Proteins 0.000 claims description 6
- 101150108780 pta gene Proteins 0.000 claims description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 4
- 229930182843 D-Lactic acid Natural products 0.000 claims description 4
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 claims description 4
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 101150014383 adhE gene Proteins 0.000 claims description 4
- 229940022769 d- lactic acid Drugs 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 101150075213 frdA gene Proteins 0.000 claims description 4
- 101150018523 frdB gene Proteins 0.000 claims description 4
- 101150087653 frdC gene Proteins 0.000 claims description 4
- 101150023570 frdD gene Proteins 0.000 claims description 4
- 125000005639 glycero group Chemical group 0.000 claims description 4
- 229940049920 malate Drugs 0.000 claims description 4
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- BLPJOIOMVXBHNL-QJBWUGSNSA-N s-[2-[3-[[(2r)-4-[[[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] ethanethioate;2-oxopropanoic acid Chemical compound CC(=O)C(O)=O.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)O[C@H]1N1C2=NC=NC(N)=C2N=C1 BLPJOIOMVXBHNL-QJBWUGSNSA-N 0.000 claims description 4
- VNOYUJKHFWYWIR-ITIYDSSPSA-N succinyl-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)CCC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 VNOYUJKHFWYWIR-ITIYDSSPSA-N 0.000 claims description 4
- 241000588919 Citrobacter freundii Species 0.000 claims description 3
- QAQREVBBADEHPA-IEXPHMLFSA-N propionyl-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@H]1N1C2=NC=NC(N)=C2N=C1 QAQREVBBADEHPA-IEXPHMLFSA-N 0.000 claims description 3
- 241000948980 Actinobacillus succinogenes Species 0.000 claims description 2
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 2
- 241000588722 Escherichia Species 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 2
- 241000179039 Paenibacillus Species 0.000 claims description 2
- 241000235070 Saccharomyces Species 0.000 claims description 2
- 235000001014 amino acid Nutrition 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 238000012258 culturing Methods 0.000 claims description 2
- 101150032129 egsA gene Proteins 0.000 claims description 2
- CNNRFBWVTKFGRE-UHFFFAOYSA-N formic acid;2-oxopropanoic acid Chemical compound OC=O.CC(=O)C(O)=O CNNRFBWVTKFGRE-UHFFFAOYSA-N 0.000 claims description 2
- 239000001963 growth medium Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 150000002596 lactones Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 101150088738 pckA gene Proteins 0.000 claims description 2
- 101150023641 ppc gene Proteins 0.000 claims description 2
- MXPOJGAZTYDWME-UHFFFAOYSA-N 1,1-dihydroxypropan-2-one;phosphoric acid Chemical compound OP(O)(O)=O.CC(=O)C(O)O.CC(=O)C(O)O MXPOJGAZTYDWME-UHFFFAOYSA-N 0.000 claims 2
- XDXFALYQLCMAQN-WLHGVMLRSA-N butanedioic acid;(e)-but-2-enedioic acid Chemical compound OC(=O)CCC(O)=O.OC(=O)\C=C\C(O)=O XDXFALYQLCMAQN-WLHGVMLRSA-N 0.000 claims 2
- NJTGANWAUPEOAX-UHFFFAOYSA-N molport-023-220-454 Chemical compound OCC(O)CO.OCC(O)CO NJTGANWAUPEOAX-UHFFFAOYSA-N 0.000 claims 2
- 241000606750 Actinobacillus Species 0.000 claims 1
- VNVUYGYPCGJLAK-IBOSZNHHSA-N [(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butyl] [hydroxy-[[(2R,3S,4R,5R)-4-hydroxy-3-phosphonooxy-5-[6-(sulfonylamino)purin-9-yl]oxolan-2-yl]methoxy]phosphoryl] hydrogen phosphate Chemical compound S(=O)(=O)=NC=1C=2N=CN([C@H]3[C@H](O)[C@H](OP(=O)(O)O)[C@@H](COP(=O)(O)OP(=O)(O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS)O3)C=2N=CN=1 VNVUYGYPCGJLAK-IBOSZNHHSA-N 0.000 claims 1
- 150000002314 glycerols Chemical class 0.000 claims 1
- 230000004060 metabolic process Effects 0.000 claims 1
- 101150067708 pckG gene Proteins 0.000 claims 1
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 claims 1
- 239000000370 acceptor Substances 0.000 description 3
- 239000001384 succinic acid Substances 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10901808P | 2008-10-28 | 2008-10-28 | |
| US61/109,018 | 2008-10-28 | ||
| PCT/US2009/062440 WO2010051324A1 (en) | 2008-10-28 | 2009-10-28 | Microaerobic cultures for converting glycerol to chemicals |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012506716A JP2012506716A (ja) | 2012-03-22 |
| JP2012506716A5 true JP2012506716A5 (enExample) | 2012-12-06 |
Family
ID=42129248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011534730A Pending JP2012506716A (ja) | 2008-10-28 | 2009-10-28 | グリセロールを化学物質に変換するための微好気性培養 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8691552B2 (enExample) |
| EP (1) | EP2350299A4 (enExample) |
| JP (1) | JP2012506716A (enExample) |
| MY (1) | MY160380A (enExample) |
| WO (1) | WO2010051324A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2350299A4 (en) | 2008-10-28 | 2012-04-25 | Univ Rice William M | MICROAEROBE CULTURES FOR THE CONVERSION OF GLYCERINE IN CHEMICALS |
| WO2011163373A1 (en) * | 2010-06-24 | 2011-12-29 | Glycos Biotechnologies, Inc. | Anaerobic fermentation methods and apparatus |
| KR101221557B1 (ko) * | 2010-08-30 | 2013-01-14 | 한국과학기술원 | 수크로오즈와 글리세롤을 동시에 이용하는 신규 숙신산 생성 변이 미생물 및 이를 이용한 숙신산 제조방법 |
| AU2012214255A1 (en) * | 2011-02-11 | 2013-09-12 | Regents Of The University Of Minnesota | Cells and methods for producing isobutyric acid |
| US10041094B2 (en) | 2011-07-22 | 2018-08-07 | Myriant Corporation | Fermentation of glycerol to organic acids |
| WO2013146557A1 (en) * | 2012-03-29 | 2013-10-03 | Mitsui Chemicals, Inc. | Biocatalysts for production of d-lactic acid from glycerol |
| AR097480A1 (es) * | 2013-08-29 | 2016-03-16 | Dsm Ip Assets Bv | Células de levadura convertidoras de glicerol y ácido acético con una conversión de ácido acético mejorada |
| CN107429271B (zh) | 2014-10-29 | 2022-03-04 | R·冈萨雷斯 | 从一碳化合物生物合成产物 |
| EP3051449A1 (de) * | 2015-01-29 | 2016-08-03 | Bayer Technology Services GmbH | Computerimplementiertes Verfahren zur Erstellung eines Fermentationsmodels |
| US11319562B2 (en) | 2015-04-15 | 2022-05-03 | Ramon Gonzalez | Modified fatty acid biosynthesis with ACP-dependent thiolases |
| US10920251B2 (en) | 2016-05-05 | 2021-02-16 | William Marsh Rice University | Microbial production of fats |
| WO2017210381A1 (en) * | 2016-06-02 | 2017-12-07 | William Marsh Rice University | Bioconversion of 1-carbon feedstocks to chemicals and fuels |
| DE102016115425A1 (de) * | 2016-08-19 | 2018-02-22 | Jacobs University Bremen Ggmbh | Gentechnisch veränderte Hefe zur Fermentation von Glycerol |
| CN107099558B (zh) * | 2017-04-25 | 2021-06-11 | 华东理工大学 | 一种同时生物合成1，3-丙二醇和乙偶姻的新方法 |
| EP3980534A4 (en) | 2019-06-04 | 2023-08-30 | Ramon Gonzalez | PRODUCTION OF 2-HYDROXYACYL-COA MOLECULES AND THEIR DERIVATIVES |
| WO2024150067A2 (en) | 2023-01-12 | 2024-07-18 | Mojia Biotech Pte. Ltd. | Acyloin condensation reactions, enzymes, and products thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5686276A (en) * | 1995-05-12 | 1997-11-11 | E. I. Du Pont De Nemours And Company | Bioconversion of a fermentable carbon source to 1,3-propanediol by a single microorganism |
| BRPI0709679B1 (pt) | 2006-03-31 | 2017-03-28 | Rice Univ | método para fermentar anaerobicamente glicerol para produzir um produto; e método de produção de 1,2-pdo |
| US8673601B2 (en) | 2007-01-22 | 2014-03-18 | Genomatica, Inc. | Methods and organisms for growth-coupled production of 3-hydroxypropionic acid |
| EP2121915B1 (en) * | 2007-03-20 | 2012-08-08 | University of Florida Research Foundation, Inc. | Materials and methods for efficient succinate and malate production |
| EP2350299A4 (en) | 2008-10-28 | 2012-04-25 | Univ Rice William M | MICROAEROBE CULTURES FOR THE CONVERSION OF GLYCERINE IN CHEMICALS |
-
2009
- 2009-10-28 EP EP09824100A patent/EP2350299A4/en not_active Withdrawn
- 2009-10-28 JP JP2011534730A patent/JP2012506716A/ja active Pending
- 2009-10-28 WO PCT/US2009/062440 patent/WO2010051324A1/en not_active Ceased
- 2009-10-28 US US13/126,499 patent/US8691552B2/en not_active Expired - Fee Related
- 2009-10-28 MY MYPI2011001452A patent/MY160380A/en unknown
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