JP2022031675A5 - - Google Patents
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- JP2022031675A5 JP2022031675A5 JP2021179960A JP2021179960A JP2022031675A5 JP 2022031675 A5 JP2022031675 A5 JP 2022031675A5 JP 2021179960 A JP2021179960 A JP 2021179960A JP 2021179960 A JP2021179960 A JP 2021179960A JP 2022031675 A5 JP2022031675 A5 JP 2022031675A5
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- JP
- Japan
- Prior art keywords
- coa
- naturally occurring
- composition
- microbial organism
- exogenous nucleic
- Prior art date
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- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 404
- 230000000813 microbial effect Effects 0.000 claims description 303
- 150000007523 nucleic acids Chemical class 0.000 claims description 248
- 102000039446 nucleic acids Human genes 0.000 claims description 248
- 108020004707 nucleic acids Proteins 0.000 claims description 248
- 230000037361 pathway Effects 0.000 claims description 245
- 102000004316 Oxidoreductases Human genes 0.000 claims description 240
- 108090000854 Oxidoreductases Proteins 0.000 claims description 240
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims description 184
- 102000004190 Enzymes Human genes 0.000 claims description 141
- 108090000790 Enzymes Proteins 0.000 claims description 141
- 238000000034 method Methods 0.000 claims description 105
- 102000003929 Transaminases Human genes 0.000 claims description 87
- 108090000340 Transaminases Proteins 0.000 claims description 87
- 229960002684 aminocaproic acid Drugs 0.000 claims description 63
- 102100026105 3-ketoacyl-CoA thiolase, mitochondrial Human genes 0.000 claims description 40
- 108010003902 Acetyl-CoA C-acyltransferase Proteins 0.000 claims description 40
- 238000004519 manufacturing process Methods 0.000 claims description 36
- 238000012258 culturing Methods 0.000 claims description 35
- 101710088194 Dehydrogenase Proteins 0.000 claims description 24
- 108090001042 Hydro-Lyases Proteins 0.000 claims description 19
- 102000004867 Hydro-Lyases Human genes 0.000 claims description 19
- SPNAEHGLBRRCGL-BIEWRJSYSA-N adipoyl-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)CCCCC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 SPNAEHGLBRRCGL-BIEWRJSYSA-N 0.000 claims description 10
- 102000005369 Aldehyde Dehydrogenase Human genes 0.000 claims description 8
- 108020002663 Aldehyde Dehydrogenase Proteins 0.000 claims description 8
- 230000001419 dependent effect Effects 0.000 claims description 8
- OTEACGAEDCIMBS-FOLKQPSDSA-N 3-hydroxyadipyl-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 OTEACGAEDCIMBS-FOLKQPSDSA-N 0.000 claims description 7
- 229960003237 betaine Drugs 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical group C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 3
- 241000894006 Bacteria Species 0.000 claims description 2
- 102000052553 3-Hydroxyacyl CoA Dehydrogenase Human genes 0.000 claims 5
- 108700020831 3-Hydroxyacyl-CoA Dehydrogenase Proteins 0.000 claims 5
- 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 5
- ZFXICKRXPZTFPB-KCQRSJHASA-N trans-2,3-didehydroadipoyl-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\CCC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 ZFXICKRXPZTFPB-KCQRSJHASA-N 0.000 claims 5
- 239000002609 medium Substances 0.000 claims 3
- 241000186394 Eubacterium Species 0.000 claims 2
- 241000233866 Fungi Species 0.000 claims 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims 2
- 241000948980 Actinobacillus succinogenes Species 0.000 claims 1
- 241000722955 Anaerobiospirillum Species 0.000 claims 1
- 241000228245 Aspergillus niger Species 0.000 claims 1
- 241001465318 Aspergillus terreus Species 0.000 claims 1
- 244000063299 Bacillus subtilis Species 0.000 claims 1
- 235000014469 Bacillus subtilis Nutrition 0.000 claims 1
- 241000193401 Clostridium acetobutylicum Species 0.000 claims 1
- 241000186226 Corynebacterium glutamicum Species 0.000 claims 1
- 241000588724 Escherichia coli Species 0.000 claims 1
- 241001473456 Eutrochium purpureum Species 0.000 claims 1
- 241000589236 Gluconobacter Species 0.000 claims 1
- 241000588749 Klebsiella oxytoca Species 0.000 claims 1
- 235000014663 Kluyveromyces fragilis Nutrition 0.000 claims 1
- 241001138401 Kluyveromyces lactis Species 0.000 claims 1
- 241000235058 Komagataella pastoris Species 0.000 claims 1
- 240000006024 Lactobacillus plantarum Species 0.000 claims 1
- 235000013965 Lactobacillus plantarum Nutrition 0.000 claims 1
- 241000589540 Pseudomonas fluorescens Species 0.000 claims 1
- 241000589776 Pseudomonas putida Species 0.000 claims 1
- 241000235527 Rhizopus Species 0.000 claims 1
- 240000005384 Rhizopus oryzae Species 0.000 claims 1
- 235000013752 Rhizopus oryzae Nutrition 0.000 claims 1
- 244000253911 Saccharomyces fragilis Species 0.000 claims 1
- 235000018368 Saccharomyces fragilis Nutrition 0.000 claims 1
- 241000235343 Saccharomycetales Species 0.000 claims 1
- 241000235347 Schizosaccharomyces pombe Species 0.000 claims 1
- 244000057717 Streptococcus lactis Species 0.000 claims 1
- 235000014897 Streptococcus lactis Nutrition 0.000 claims 1
- 241000187432 Streptomyces coelicolor Species 0.000 claims 1
- 241000588902 Zymomonas mobilis Species 0.000 claims 1
- 238000005119 centrifugation Methods 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 238000000909 electrodialysis Methods 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 239000001963 growth medium Substances 0.000 claims 1
- 238000004255 ion exchange chromatography Methods 0.000 claims 1
- 229940031154 kluyveromyces marxianus Drugs 0.000 claims 1
- 229940072205 lactobacillus plantarum Drugs 0.000 claims 1
- 238000000622 liquid--liquid extraction Methods 0.000 claims 1
- 239000012528 membrane Substances 0.000 claims 1
- 238000005374 membrane filtration Methods 0.000 claims 1
- 238000005373 pervaporation Methods 0.000 claims 1
- 238000001223 reverse osmosis Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 238000001542 size-exclusion chromatography Methods 0.000 claims 1
- 238000000638 solvent extraction Methods 0.000 claims 1
- 238000001179 sorption measurement Methods 0.000 claims 1
- 238000000108 ultra-filtration Methods 0.000 claims 1
- 102000004357 Transferases Human genes 0.000 description 60
- 108090000992 Transferases Proteins 0.000 description 60
- IYNRULSFFKEOLT-UHFFFAOYSA-N 3-oxopimelic acid Chemical compound OC(=O)CCCC(=O)CC(O)=O IYNRULSFFKEOLT-UHFFFAOYSA-N 0.000 description 46
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 44
- 102000003960 Ligases Human genes 0.000 description 40
- 108090000364 Ligases Proteins 0.000 description 40
- NMDDZEVVQDPECF-LURJTMIESA-N (2s)-2,7-diaminoheptanoic acid Chemical compound NCCCCC[C@H](N)C(O)=O NMDDZEVVQDPECF-LURJTMIESA-N 0.000 description 35
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 34
- SYKWLIJQEHRDNH-CKRMAKSASA-N glutaryl-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)CCCC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 SYKWLIJQEHRDNH-CKRMAKSASA-N 0.000 description 33
- MIPJCYQFTDLIGF-HDRQGHTBSA-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] 6-aminohexanethioate 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)CCCCCN)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MIPJCYQFTDLIGF-HDRQGHTBSA-N 0.000 description 33
- GSDLHWPNIOWYHJ-UHFFFAOYSA-N 2-amino-7-oxoheptanoic acid Chemical compound OC(=O)C(N)CCCCC=O GSDLHWPNIOWYHJ-UHFFFAOYSA-N 0.000 description 32
- KJXFOFKTZDJLMQ-UYRKPTJQSA-N 3-oxopimeloyl-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)CCCC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 KJXFOFKTZDJLMQ-UYRKPTJQSA-N 0.000 description 32
- 102000001390 Fructose-Bisphosphate Aldolase Human genes 0.000 description 24
- 108010068561 Fructose-Bisphosphate Aldolase Proteins 0.000 description 24
- FGSBMPLRSMYGCV-UHFFFAOYSA-N 2,4-dioxooctanoic acid Chemical compound CCCCC(=O)CC(=O)C(O)=O FGSBMPLRSMYGCV-UHFFFAOYSA-N 0.000 description 22
- OKDNHROSUNKBKT-UHFFFAOYSA-N 3-amino-7-oxoheptanoic acid Chemical compound OC(=O)CC(N)CCCC=O OKDNHROSUNKBKT-UHFFFAOYSA-N 0.000 description 18
- 229940040102 levulinic acid Drugs 0.000 description 17
- YMNZNYSOUAKJAV-HDRQGHTBSA-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] 6-amino-3-oxohexanethioate 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)CCCN)O[C@H]1N1C2=NC=NC(N)=C2N=C1 YMNZNYSOUAKJAV-HDRQGHTBSA-N 0.000 description 17
- RGUBYIAMAWCQSP-UHFFFAOYSA-N 3-aminoheptanedioic acid Chemical compound OC(=O)CC(N)CCCC(O)=O RGUBYIAMAWCQSP-UHFFFAOYSA-N 0.000 description 16
- PNPPVRALIYXJBW-UHFFFAOYSA-N 6-oxohexanoic acid Chemical compound OC(=O)CCCCC=O PNPPVRALIYXJBW-UHFFFAOYSA-N 0.000 description 16
- 101710202061 N-acetyltransferase Proteins 0.000 description 16
- 108091000080 Phosphotransferase Proteins 0.000 description 16
- 102000020233 phosphotransferase Human genes 0.000 description 16
- JUQLUIFNNFIIKC-UHFFFAOYSA-N 2-aminopimelic acid Chemical compound OC(=O)C(N)CCCCC(O)=O JUQLUIFNNFIIKC-UHFFFAOYSA-N 0.000 description 15
- PJDINCOFOROBQW-UHFFFAOYSA-N 3,7-Diaminoheptanoic Acid Chemical compound NCCCCC(N)CC(O)=O PJDINCOFOROBQW-UHFFFAOYSA-N 0.000 description 15
- 102000002932 Thiolase Human genes 0.000 description 14
- 108060008225 Thiolase Proteins 0.000 description 14
- RRGHQGSYMGPKCO-UHFFFAOYSA-N 7-amino-3-oxoheptanoic acid Chemical compound NCCCCC(=O)CC(O)=O RRGHQGSYMGPKCO-UHFFFAOYSA-N 0.000 description 13
- 108010069175 acyl-CoA transferase Proteins 0.000 description 13
- 101000985286 Escherichia coli 2-oxo-hept-4-ene-1,7-dioate hydratase Proteins 0.000 description 12
- WDSCBUNMANHPFH-UHFFFAOYSA-M 6-acetamidohexanoate Chemical compound CC(=O)NCCCCCC([O-])=O WDSCBUNMANHPFH-UHFFFAOYSA-M 0.000 description 11
- 102000004317 Lyases Human genes 0.000 description 11
- 108090000856 Lyases Proteins 0.000 description 11
- 238000005576 amination reaction Methods 0.000 description 11
- WRJPJZTWQTUPQK-UHFFFAOYSA-N n-(6-aminohexyl)acetamide Chemical compound CC(=O)NCCCCCCN WRJPJZTWQTUPQK-UHFFFAOYSA-N 0.000 description 11
- -1 3-Hydroxy-6-aminohexanoyl-CoA aldehyde Chemical class 0.000 description 10
- 102000001253 Protein Kinase Human genes 0.000 description 10
- 150000001408 amides Chemical class 0.000 description 10
- 108060006633 protein kinase Proteins 0.000 description 10
- 244000005700 microbiome Species 0.000 description 9
- BGJIRLKEICEKSQ-UHFFFAOYSA-N 7-amino-2-oxoheptanoic acid Chemical compound NCCCCCC(=O)C(O)=O BGJIRLKEICEKSQ-UHFFFAOYSA-N 0.000 description 8
- UWMORNRVRUIQPR-HDRQGHTBSA-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] 6-aminohex-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=CCCCN)O[C@H]1N1C2=NC=NC(N)=C2N=C1 UWMORNRVRUIQPR-HDRQGHTBSA-N 0.000 description 8
- PKVRQLMDAMASTB-SNIDVWGTSA-N 2-amino-7-[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]-7-oxoheptanoic 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)CCCCC(N)C(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 PKVRQLMDAMASTB-SNIDVWGTSA-N 0.000 description 7
- CCYXEHOXJOKCCJ-UHFFFAOYSA-N 6-aminohexanal Chemical compound NCCCCCC=O CCYXEHOXJOKCCJ-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 210000001808 exosome Anatomy 0.000 description 6
- QAMKYKJQNLRRAJ-UHFFFAOYSA-N 6-amino-3-hydroxyhexanoic acid Chemical compound NCCCC(O)CC(O)=O QAMKYKJQNLRRAJ-UHFFFAOYSA-N 0.000 description 5
- BHDKTGQTZOBVIL-UYRKPTJQSA-N 7-[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]-3,7-dioxoheptanoic 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)CCCC(=O)CC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 BHDKTGQTZOBVIL-UYRKPTJQSA-N 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- ZFXICKRXPZTFPB-FZHFFJAKSA-N (Z)-2,3-dehydroadipoyl-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/CCC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 ZFXICKRXPZTFPB-FZHFFJAKSA-N 0.000 description 4
- FOKABCOGWXJDTD-IMKGSZBMSA-N 2-amino-7-[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]-5-hydroxy-7-oxoheptanoic 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)CCC(N)C(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 FOKABCOGWXJDTD-IMKGSZBMSA-N 0.000 description 4
- HABHUTWTLGRDDU-UHFFFAOYSA-N 2-oxopimelic acid Chemical compound OC(=O)CCCCC(=O)C(O)=O HABHUTWTLGRDDU-UHFFFAOYSA-N 0.000 description 4
- SNACICYKKILLEK-UHFFFAOYSA-N 6-aminohex-2-enoic acid Chemical compound NCCCC=CC(O)=O SNACICYKKILLEK-UHFFFAOYSA-N 0.000 description 4
- ICGKEQXHPZUYSF-UHFFFAOYSA-N 6-oxohept-3-enedioic acid Chemical compound OC(=O)CC=CCC(=O)C(O)=O ICGKEQXHPZUYSF-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 108010060146 pyruvate formate-lyase activating enzyme Proteins 0.000 description 4
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 3
- DUXOPGJKCDTPLF-JXUSAFQPSA-N 3-amino-7-[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]-7-oxoheptanoic 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)CCCC(N)CC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 DUXOPGJKCDTPLF-JXUSAFQPSA-N 0.000 description 3
- 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 description 3
- PUIRLTLMCJRHFF-UHFFFAOYSA-N 6-amino-3-oxohexanoic acid Chemical compound NCCCC(=O)CC(O)=O PUIRLTLMCJRHFF-UHFFFAOYSA-N 0.000 description 3
- WFSCDWVPBNOBNO-UHFFFAOYSA-N 7-amino-2-oxohept-3-enoic acid Chemical compound NCCCC=CC(=O)C(O)=O WFSCDWVPBNOBNO-UHFFFAOYSA-N 0.000 description 3
- QQUWQLAQVGXPPE-UHFFFAOYSA-N 7-amino-4-hydroxy-2-oxoheptanoic acid Chemical compound NCCCC(O)CC(=O)C(O)=O QQUWQLAQVGXPPE-UHFFFAOYSA-N 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- LKNUIOZKLGQZEF-UHFFFAOYSA-N n-(6-oxohexyl)acetamide Chemical compound CC(=O)NCCCCCC=O LKNUIOZKLGQZEF-UHFFFAOYSA-N 0.000 description 3
- FPZRHFKFGHMXTD-UHFFFAOYSA-N 2,3-dioxooctanoic acid Chemical compound CCCCCC(=O)C(=O)C(O)=O FPZRHFKFGHMXTD-UHFFFAOYSA-N 0.000 description 2
- URKANQMYNHOVKS-RCICKGJNSA-N 3-amino-8-[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]-8-oxooct-6-enoic 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)C=CCCC(N)CC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 URKANQMYNHOVKS-RCICKGJNSA-N 0.000 description 2
- RTGHRDFWYQHVFW-UHFFFAOYSA-N 3-oxoadipic acid Chemical compound OC(=O)CCC(=O)CC(O)=O RTGHRDFWYQHVFW-UHFFFAOYSA-N 0.000 description 2
- 108010027577 3-oxoadipyl-coenzyme A thiolase Proteins 0.000 description 2
- HNOAJOYERZTSNK-UHFFFAOYSA-N 4-hydroxy-2-oxoheptanedioic acid Chemical group OC(=O)CCC(O)CC(=O)C(O)=O HNOAJOYERZTSNK-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 102000057234 Acyl transferases Human genes 0.000 description 2
- 108700016155 Acyl transferases Proteins 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 235000015250 liver sausages Nutrition 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
- XDWUDFWWMNXIJN-UHFFFAOYSA-N phosphono 6-aminohexanoate Chemical compound NCCCCCC(=O)OP(O)(O)=O XDWUDFWWMNXIJN-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
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- 230000002269 spontaneous effect Effects 0.000 description 2
- CLGRLBOVAMSRKG-UHFFFAOYSA-N 6-aminohept-3-enedioic acid Chemical compound OC(=O)C(N)CC=CCC(O)=O CLGRLBOVAMSRKG-UHFFFAOYSA-N 0.000 description 1
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- QPMJENKZJUFOON-PLNGDYQASA-N ethyl (z)-3-chloro-2-cyano-4,4,4-trifluorobut-2-enoate Chemical compound CCOC(=O)C(\C#N)=C(/Cl)C(F)(F)F QPMJENKZJUFOON-PLNGDYQASA-N 0.000 description 1
- 108010008221 formate C-acetyltransferase Proteins 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- OTAIDQCHVKFDQZ-UHFFFAOYSA-N phosphono 6-acetamidohexanoate Chemical compound CC(=O)NCCCCCC(=O)OP(O)(O)=O OTAIDQCHVKFDQZ-UHFFFAOYSA-N 0.000 description 1
- QJRBJEADDJCUDL-CECATXLMSA-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] 6-acetamidohexanethioate 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)CCCCCNC(=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 QJRBJEADDJCUDL-CECATXLMSA-N 0.000 description 1
- HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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