MX2013001071A - Microorganismos y metodos para la biosintesis de aromaticos, 2, 4-pentadienoato y 1, 3-butadieno. - Google Patents
Microorganismos y metodos para la biosintesis de aromaticos, 2, 4-pentadienoato y 1, 3-butadieno.Info
- Publication number
- MX2013001071A MX2013001071A MX2013001071A MX2013001071A MX2013001071A MX 2013001071 A MX2013001071 A MX 2013001071A MX 2013001071 A MX2013001071 A MX 2013001071A MX 2013001071 A MX2013001071 A MX 2013001071A MX 2013001071 A MX2013001071 A MX 2013001071A
- Authority
- MX
- Mexico
- Prior art keywords
- coa
- reductase
- dehydratase
- decarboxylase
- exogenous nucleic
- Prior art date
Links
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims abstract 102
- 238000000034 method Methods 0.000 title claims abstract 83
- SDVVLIIVFBKBMG-UHFFFAOYSA-N penta-2,4-dienoic acid Chemical compound OC(=O)C=CC=C SDVVLIIVFBKBMG-UHFFFAOYSA-N 0.000 title claims abstract 41
- 244000005700 microbiome Species 0.000 title claims 98
- 230000015572 biosynthetic process Effects 0.000 title claims 61
- 230000000813 microbial effect Effects 0.000 claims abstract 306
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract 120
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract 102
- 230000037361 pathway Effects 0.000 claims abstract 66
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract 44
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract 38
- LPNBBFKOUUSUDB-UHFFFAOYSA-M p-toluate Chemical compound CC1=CC=C(C([O-])=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-M 0.000 claims abstract 24
- 102000004316 Oxidoreductases Human genes 0.000 claims 328
- 108090000854 Oxidoreductases Proteins 0.000 claims 328
- 150000007523 nucleic acids Chemical class 0.000 claims 226
- 102000039446 nucleic acids Human genes 0.000 claims 226
- 108020004707 nucleic acids Proteins 0.000 claims 226
- 102000004867 Hydro-Lyases Human genes 0.000 claims 225
- 108090001042 Hydro-Lyases Proteins 0.000 claims 225
- 108090000489 Carboxy-Lyases Proteins 0.000 claims 168
- 102000004190 Enzymes Human genes 0.000 claims 122
- 108090000790 Enzymes Proteins 0.000 claims 122
- 102000004357 Transferases Human genes 0.000 claims 120
- 108090000992 Transferases Proteins 0.000 claims 120
- 102000004157 Hydrolases Human genes 0.000 claims 110
- 108090000604 Hydrolases Proteins 0.000 claims 110
- 102000003960 Ligases Human genes 0.000 claims 104
- 108090000364 Ligases Proteins 0.000 claims 104
- RGPXHQLKXPEHMD-UHFFFAOYSA-N 3,5-dihydroxypentanoic acid Chemical compound OCCC(O)CC(O)=O RGPXHQLKXPEHMD-UHFFFAOYSA-N 0.000 claims 86
- 102100026105 3-ketoacyl-CoA thiolase, mitochondrial Human genes 0.000 claims 84
- 108010003902 Acetyl-CoA C-acyltransferase Proteins 0.000 claims 84
- OYCNZOVOKFUQPU-CKRMAKSASA-N 5-[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]ethylsulfanyl]-3,5-dioxopentanoic acid 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)CC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 OYCNZOVOKFUQPU-CKRMAKSASA-N 0.000 claims 60
- LTYOQGRJFJAKNA-KKIMTKSISA-N Malonyl CoA Natural products S(C(=O)CC(=O)O)CCNC(=O)CCNC(=O)[C@@H](O)C(CO[P@](=O)(O[P@](=O)(OC[C@H]1[C@@H](OP(=O)(O)O)[C@@H](O)[C@@H](n2c3ncnc(N)c3nc2)O1)O)O)(C)C LTYOQGRJFJAKNA-KKIMTKSISA-N 0.000 claims 60
- LTYOQGRJFJAKNA-DVVLENMVSA-N malonyl-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)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 LTYOQGRJFJAKNA-DVVLENMVSA-N 0.000 claims 60
- 108020002494 acetyltransferase Proteins 0.000 claims 58
- 102000005421 acetyltransferase Human genes 0.000 claims 58
- CUBSYRCTISCQAF-UHFFFAOYSA-N 5-hydroxypent-2-enoic acid Chemical compound OCCC=CC(O)=O CUBSYRCTISCQAF-UHFFFAOYSA-N 0.000 claims 50
- 150000001299 aldehydes Chemical class 0.000 claims 48
- BERBFZCUSMQABM-IEXPHMLFSA-N 3-hydroxypropanoyl-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)CCO)O[C@H]1N1C2=NC=NC(N)=C2N=C1 BERBFZCUSMQABM-IEXPHMLFSA-N 0.000 claims 42
- KGWOBFSKGHXRMY-ZMHDXICWSA-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] 5-hydroxy-3-oxopentanethioate 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)CCO)O[C@H]1N1C2=NC=NC(N)=C2N=C1 KGWOBFSKGHXRMY-ZMHDXICWSA-N 0.000 claims 41
- ANTBRXMMNBUYMS-UHFFFAOYSA-N 5-hydroxy-3-oxopentanoic acid Chemical compound OCCC(=O)CC(O)=O ANTBRXMMNBUYMS-UHFFFAOYSA-N 0.000 claims 37
- 101710088194 Dehydrogenase Proteins 0.000 claims 37
- 150000002576 ketones Chemical class 0.000 claims 36
- AINRQBNLOBQURT-UHFFFAOYSA-N 3-hydroxypent-4-enoic acid Chemical compound C=CC(O)CC(O)=O AINRQBNLOBQURT-UHFFFAOYSA-N 0.000 claims 34
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 34
- 239000001963 growth medium Substances 0.000 claims 29
- ZSPTYLOMNJNZNG-UHFFFAOYSA-N 3-Buten-1-ol Chemical compound OCCC=C ZSPTYLOMNJNZNG-UHFFFAOYSA-N 0.000 claims 26
- ZHBPKXTYCQYISG-UHFFFAOYSA-N 3-hydroxy-5-oxopentanoic acid Chemical compound O=CCC(O)CC(O)=O ZHBPKXTYCQYISG-UHFFFAOYSA-N 0.000 claims 24
- IIYZSYKTQRIPRG-MJBWAWCGSA-N 5-[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]ethylsulfanyl]-3-hydroxy-5-oxopentanoic acid 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)CC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 IIYZSYKTQRIPRG-MJBWAWCGSA-N 0.000 claims 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 24
- 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 24
- POODSGUMUCVRTR-IEXPHMLFSA-N acryloyl-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[C@H]1N1C2=NC=NC(N)=C2N=C1 POODSGUMUCVRTR-IEXPHMLFSA-N 0.000 claims 23
- DAZFQYSXXSTLKW-UHFFFAOYSA-N 3,5-dioxopentanoic acid Chemical compound OC(=O)CC(=O)CC=O DAZFQYSXXSTLKW-UHFFFAOYSA-N 0.000 claims 22
- 108010074122 Ferredoxins Proteins 0.000 claims 20
- 108010020056 Hydrogenase Proteins 0.000 claims 20
- 108010031234 carbon monoxide dehydrogenase Proteins 0.000 claims 20
- 102000001253 Protein Kinase Human genes 0.000 claims 19
- 238000004519 manufacturing process Methods 0.000 claims 19
- RTGHRDFWYQHVFW-UHFFFAOYSA-N 3-oxoadipic acid Chemical compound OC(=O)CCC(=O)CC(O)=O RTGHRDFWYQHVFW-UHFFFAOYSA-N 0.000 claims 18
- 238000012258 culturing Methods 0.000 claims 17
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 claims 17
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims 17
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims 16
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 16
- 230000009331 reductive pathway Effects 0.000 claims 15
- 101710182361 Pyruvate:ferredoxin oxidoreductase Proteins 0.000 claims 14
- 108050008280 Shikimate dehydrogenase Proteins 0.000 claims 14
- IISXAOCGJOIGLD-UHFFFAOYSA-N 2-hydroxypent-2-enoic acid Chemical compound CCC=C(O)C(O)=O IISXAOCGJOIGLD-UHFFFAOYSA-N 0.000 claims 12
- IWARWSDDJHGZOW-UHFFFAOYSA-N 2-oxopent-3-enoic acid Chemical compound CC=CC(=O)C(O)=O IWARWSDDJHGZOW-UHFFFAOYSA-N 0.000 claims 12
- YVOMYDHIQVMMTA-UHFFFAOYSA-N 3-Hydroxyadipic acid Chemical compound OC(=O)CC(O)CCC(O)=O YVOMYDHIQVMMTA-UHFFFAOYSA-N 0.000 claims 12
- HXUIDZOMTRMIOE-UHFFFAOYSA-M 3-oxo-3-phenylpropionate Chemical compound [O-]C(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-M 0.000 claims 12
- GQLBISHKIZPYFT-ZMHDXICWSA-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] 5-hydroxypent-2-enethioate 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=CCCO)O[C@H]1N1C2=NC=NC(N)=C2N=C1 GQLBISHKIZPYFT-ZMHDXICWSA-N 0.000 claims 12
- 108090000340 Transaminases Proteins 0.000 claims 12
- 102000003929 Transaminases Human genes 0.000 claims 12
- 230000009615 deamination Effects 0.000 claims 12
- 238000006481 deamination reaction Methods 0.000 claims 12
- 108010038980 phenylalanine aminotransferase Proteins 0.000 claims 12
- 108060006633 protein kinase Proteins 0.000 claims 12
- UUFDQTFCJFWTDW-XMWLYHNJSA-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] 3,5-dihydroxypentanethioate 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)CCO)O[C@H]1N1C2=NC=NC(N)=C2N=C1 UUFDQTFCJFWTDW-XMWLYHNJSA-N 0.000 claims 12
- KSSFGJUSMXZBDD-UHFFFAOYSA-N 3-oxo-4-pentenoic acid Chemical compound OC(=O)CC(=O)C=C KSSFGJUSMXZBDD-UHFFFAOYSA-N 0.000 claims 11
- HFKQINMYQUXOCH-UHFFFAOYSA-N 4-hydroxy-2-oxopentanoic acid Chemical compound CC(O)CC(=O)C(O)=O HFKQINMYQUXOCH-UHFFFAOYSA-N 0.000 claims 11
- PMJHHCWVYXUKFD-UHFFFAOYSA-N penta-1,3-diene Chemical compound CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims 11
- 229930029653 phosphoenolpyruvate Natural products 0.000 claims 11
- DTBNBXWJWCWCIK-UHFFFAOYSA-K phosphonatoenolpyruvate Chemical compound [O-]C(=O)C(=C)OP([O-])([O-])=O DTBNBXWJWCWCIK-UHFFFAOYSA-K 0.000 claims 11
- 102000009836 Aconitate hydratase Human genes 0.000 claims 10
- 108010009924 Aconitate hydratase Proteins 0.000 claims 10
- 108010036781 Fumarate Hydratase Proteins 0.000 claims 10
- 102100036160 Fumarate hydratase, mitochondrial Human genes 0.000 claims 10
- 108010026217 Malate Dehydrogenase Proteins 0.000 claims 10
- 102000013460 Malate Dehydrogenase Human genes 0.000 claims 10
- 102000019259 Succinate Dehydrogenase Human genes 0.000 claims 10
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- 108010075728 Succinate-CoA Ligases Proteins 0.000 claims 10
- 102000011929 Succinate-CoA Ligases Human genes 0.000 claims 10
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 claims 10
- KPGXRSRHYNQIFN-UHFFFAOYSA-L 2-oxoglutarate(2-) Chemical compound [O-]C(=O)CCC(=O)C([O-])=O KPGXRSRHYNQIFN-UHFFFAOYSA-L 0.000 claims 9
- 102000012011 Isocitrate Dehydrogenase Human genes 0.000 claims 9
- 108010075869 Isocitrate Dehydrogenase Proteins 0.000 claims 9
- 108091000041 Phosphoenolpyruvate Carboxylase Proteins 0.000 claims 9
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 claims 8
- PMYFHWSFYMMYNX-UHFFFAOYSA-N CC(C=C1)=CC=C1C(OOP(O)=O)=O Chemical compound CC(C=C1)=CC=C1C(OOP(O)=O)=O PMYFHWSFYMMYNX-UHFFFAOYSA-N 0.000 claims 8
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- BOSUGMLPFMPVMR-UHFFFAOYSA-N OP(OOC(C1=CC=CC=C1)=O)=O Chemical compound OP(OOC(C1=CC=CC=C1)=O)=O BOSUGMLPFMPVMR-UHFFFAOYSA-N 0.000 claims 8
- 108010036076 Phenylpyruvate decarboxylase Proteins 0.000 claims 8
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims 8
- SRUCYNCHUFMZIT-UHFFFAOYSA-N acetyl prop-2-enoate Chemical compound CC(=O)OC(=O)C=C SRUCYNCHUFMZIT-UHFFFAOYSA-N 0.000 claims 8
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 claims 8
- VEVJTUNLALKRNO-TYHXJLICSA-N benzoyl-CoA Chemical compound O=C([C@H](O)C(C)(COP(O)(=O)OP(O)(=O)OC[C@@H]1[C@H]([C@@H](O)[C@@H](O1)N1C2=NC=NC(N)=C2N=C1)OP(O)(O)=O)C)NCCC(=O)NCCSC(=O)C1=CC=CC=C1 VEVJTUNLALKRNO-TYHXJLICSA-N 0.000 claims 8
- 229940049953 phenylacetate Drugs 0.000 claims 8
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 8
- 108010038550 3-dehydroquinate dehydratase Proteins 0.000 claims 7
- 108050006180 3-dehydroquinate synthase Proteins 0.000 claims 7
- 108010092060 Acetate kinase Proteins 0.000 claims 7
- 108020001482 shikimate kinase Proteins 0.000 claims 7
- VKKKAAPGXHWXOO-BIEWRJSYSA-N 3-oxoadipyl-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)CCC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 VKKKAAPGXHWXOO-BIEWRJSYSA-N 0.000 claims 6
- YANJKPZKTWMMOF-UHFFFAOYSA-N 4-hydroxypent-2-enoic acid Chemical compound CC(O)C=CC(O)=O YANJKPZKTWMMOF-UHFFFAOYSA-N 0.000 claims 6
- 108060000712 Benzoate-CoA ligase Proteins 0.000 claims 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 6
- NGHMDNPXVRFFGS-IUYQGCFVSA-N D-erythrose 4-phosphate Chemical compound O=C[C@H](O)[C@H](O)COP(O)(O)=O NGHMDNPXVRFFGS-IUYQGCFVSA-N 0.000 claims 6
- SLFXWYTTWMIAKE-UHFFFAOYSA-N OP(OOCC(CC=O)=O)=O Chemical compound OP(OOCC(CC=O)=O)=O SLFXWYTTWMIAKE-UHFFFAOYSA-N 0.000 claims 6
- 229940100595 phenylacetaldehyde Drugs 0.000 claims 6
- MGKKVVWYGTWMNB-ZMHDXICWSA-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] 3-oxopent-4-enethioate 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=C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MGKKVVWYGTWMNB-ZMHDXICWSA-N 0.000 claims 6
- 108010049926 Acetate-CoA ligase Proteins 0.000 claims 5
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- 108010091694 benzoyl-coenzyme A reductase (dearomatizing) Proteins 0.000 claims 5
- UVPLYHXZJGQOQS-SXQYHYLKSA-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] 4-methylbenzenecarbothioate Chemical compound C1=CC(C)=CC=C1C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@H]1[C@@H](OP(O)(O)=O)[C@@H](O)[C@H](N2C3=NC=NC(N)=C3N=C2)O1 UVPLYHXZJGQOQS-SXQYHYLKSA-N 0.000 claims 5
- PCEJMSIIDXUDSN-UHFFFAOYSA-O 2,4-diazaniumylpentanoate Chemical compound CC([NH3+])CC([NH3+])C([O-])=O PCEJMSIIDXUDSN-UHFFFAOYSA-O 0.000 claims 4
- QTSNVMMGKAPSRT-UHFFFAOYSA-N 2-Hydroxy-4-oxopentanoic acid Chemical compound CC(=O)CC(O)C(O)=O QTSNVMMGKAPSRT-UHFFFAOYSA-N 0.000 claims 4
- SBRVJFMQKPUAGQ-UHFFFAOYSA-N 2-amino-4-hydroxypentanoic acid Chemical compound CC(O)CC(N)C(O)=O SBRVJFMQKPUAGQ-UHFFFAOYSA-N 0.000 claims 4
- 108010036824 Citrate (pro-3S)-lyase Proteins 0.000 claims 4
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 4
- 108010055471 Phenylacetaldehyde dehydrogenase Proteins 0.000 claims 4
- 241000718541 Tetragastris balsamifera Species 0.000 claims 4
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- 108010029348 4-hydroxy-2-oxovalerate aldolase Proteins 0.000 claims 3
- 101100501444 Escherichia phage P1 17 gene Proteins 0.000 claims 3
- 230000002829 reductive effect Effects 0.000 claims 3
- -1 (2-hydroxy) 4-oxobutoxy Chemical group 0.000 claims 2
- 108010068049 1-deoxy-D-xylulose 5-phosphate reductoisomerase Proteins 0.000 claims 2
- 101710108218 2-amino-4-ketopentanoate thiolase alpha subunit Proteins 0.000 claims 2
- 101710176589 2-amino-4-ketopentanoate thiolase beta subunit Proteins 0.000 claims 2
- OLNQPHNMSVWNHS-UHFFFAOYSA-N CC(C(COOP(O)=O)O)C=O Chemical compound CC(C(COOP(O)=O)O)C=O OLNQPHNMSVWNHS-UHFFFAOYSA-N 0.000 claims 2
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- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims 2
- 108010060155 deoxyxylulose-5-phosphate synthase Proteins 0.000 claims 2
- 229960003104 ornithine Drugs 0.000 claims 2
- KDOCIZRMPUBINQ-XMWLYHNJSA-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] 3-hydroxypent-4-enethioate 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=C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 KDOCIZRMPUBINQ-XMWLYHNJSA-N 0.000 claims 2
- 102000004146 ATP citrate synthases Human genes 0.000 claims 1
- 108090000662 ATP citrate synthases Proteins 0.000 claims 1
- 241000511343 Chondrostoma nasus Species 0.000 claims 1
- 108010068561 Fructose-Bisphosphate Aldolase Proteins 0.000 claims 1
- 102000001390 Fructose-Bisphosphate Aldolase Human genes 0.000 claims 1
- 244000287680 Garcinia dulcis Species 0.000 claims 1
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims 1
- 241000283984 Rodentia Species 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 230000030609 dephosphorylation Effects 0.000 claims 1
- 238000006209 dephosphorylation reaction Methods 0.000 claims 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 1
- TXXHDPDFNKHHGW-ZPUQHVIOSA-N trans,trans-muconic acid Chemical compound OC(=O)\C=C\C=C\C(O)=O TXXHDPDFNKHHGW-ZPUQHVIOSA-N 0.000 claims 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 claims 1
- GCMYVFQOSTYQRJ-UHFFFAOYSA-N (2-hydroxy-3-methyl-4-oxobutyl) dihydrogen phosphate Chemical compound O=CC(C)C(O)COP(O)(O)=O GCMYVFQOSTYQRJ-UHFFFAOYSA-N 0.000 abstract 2
- LQIRHIGPILJQHV-UHFFFAOYSA-N (2-hydroxy-4-oxobutyl) dihydrogen phosphate Chemical compound O=CCC(O)COP(O)(O)=O LQIRHIGPILJQHV-UHFFFAOYSA-N 0.000 abstract 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 abstract 2
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- C12N1/00—Microorganisms, e.g. protozoa; 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
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- 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
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- C12P5/00—Preparation of hydrocarbons or halogenated hydrocarbons
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- C12P5/00—Preparation of hydrocarbons or halogenated hydrocarbons
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- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
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- C12P7/16—Butanols
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- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/22—Preparation of oxygen-containing organic compounds containing a hydroxy group aromatic
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- C12P7/00—Preparation of oxygen-containing organic compounds
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- C12P9/00—Preparation of organic compounds containing a metal or atom other than H, N, C, O, S or halogen
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- 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
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
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Applications Claiming Priority (4)
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| US36779210P | 2010-07-26 | 2010-07-26 | |
| US36822310P | 2010-07-27 | 2010-07-27 | |
| US38140710P | 2010-09-09 | 2010-09-09 | |
| PCT/US2011/045364 WO2012018624A2 (en) | 2010-07-26 | 2011-07-26 | Microorganisms and methods for the biosynthesis of aromatics, 2,4-pentadienoate and 1,3-butadiene |
Publications (1)
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| MX2013001071A true MX2013001071A (es) | 2013-06-28 |
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| MX2013001071A MX2013001071A (es) | 2010-07-26 | 2011-07-26 | Microorganismos y metodos para la biosintesis de aromaticos, 2, 4-pentadienoato y 1, 3-butadieno. |
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| SG (1) | SG187174A1 (enExample) |
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| WO2010144746A2 (en) * | 2009-06-10 | 2010-12-16 | Genomatica, Inc. | Microorganisms and methods for carbon-efficient biosynthesis of mek and 2-butanol |
| KR20120120493A (ko) | 2009-12-10 | 2012-11-01 | 게노마티카 인코포레이티드 | 합성 가스 또는 기타 가스상 탄소원 및 메탄올을 1,3-부탄디올로 변환하는 방법 및 변환용 유기체 |
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-
2011
- 2011-07-26 BR BR112013001635A patent/BR112013001635A2/pt not_active Application Discontinuation
- 2011-07-26 EP EP17186621.3A patent/EP3312284A3/en not_active Withdrawn
- 2011-07-26 JP JP2013521907A patent/JP2013535203A/ja active Pending
- 2011-07-26 CN CN2011800368376A patent/CN103025877A/zh active Pending
- 2011-07-26 KR KR1020137002003A patent/KR20130043170A/ko not_active Withdrawn
- 2011-07-26 EP EP13154607.9A patent/EP2607340B1/en not_active Not-in-force
- 2011-07-26 MX MX2013001071A patent/MX2013001071A/es not_active Application Discontinuation
- 2011-07-26 CA CA2806230A patent/CA2806230A1/en not_active Abandoned
- 2011-07-26 AU AU2011286199A patent/AU2011286199A1/en not_active Abandoned
- 2011-07-26 PH PH1/2013/500158A patent/PH12013500158A1/en unknown
- 2011-07-26 US US13/191,375 patent/US8715957B2/en active Active
- 2011-07-26 SG SG2013005194A patent/SG187174A1/en unknown
- 2011-07-26 WO PCT/US2011/045364 patent/WO2012018624A2/en not_active Ceased
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2013
- 2013-02-25 CO CO13037828A patent/CO6680664A2/es unknown
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2014
- 2014-03-26 US US14/226,631 patent/US9556461B2/en not_active Expired - Fee Related
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2016
- 2016-12-02 JP JP2016235414A patent/JP2017060518A/ja active Pending
- 2016-12-19 US US15/383,941 patent/US10793882B2/en active Active
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2021
- 2021-04-07 US US17/225,034 patent/US20220056488A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2017060518A (ja) | 2017-03-30 |
| KR20130043170A (ko) | 2013-04-29 |
| US20120021478A1 (en) | 2012-01-26 |
| US20150064750A1 (en) | 2015-03-05 |
| CN103025877A (zh) | 2013-04-03 |
| PH12013500158A1 (en) | 2013-03-11 |
| WO2012018624A2 (en) | 2012-02-09 |
| SG187174A1 (en) | 2013-02-28 |
| EP2607340A1 (en) | 2013-06-26 |
| WO2012018624A3 (en) | 2012-08-09 |
| BR112013001635A2 (pt) | 2016-05-24 |
| EP2607340B1 (en) | 2017-09-06 |
| AU2011286199A1 (en) | 2013-02-14 |
| CO6680664A2 (es) | 2013-05-31 |
| EP3312284A3 (en) | 2018-05-30 |
| US10793882B2 (en) | 2020-10-06 |
| EP3312284A2 (en) | 2018-04-25 |
| US20220056488A1 (en) | 2022-02-24 |
| US8715957B2 (en) | 2014-05-06 |
| US9556461B2 (en) | 2017-01-31 |
| JP2013535203A (ja) | 2013-09-12 |
| CA2806230A1 (en) | 2012-02-09 |
| US20170335352A1 (en) | 2017-11-23 |
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