FI81115C - Foerfarande foer framstaellning av optiskt aktiva -substituerade -hydroxibutansyraderivat. - Google Patents
Foerfarande foer framstaellning av optiskt aktiva -substituerade -hydroxibutansyraderivat. Download PDFInfo
- Publication number
- FI81115C FI81115C FI834419A FI834419A FI81115C FI 81115 C FI81115 C FI 81115C FI 834419 A FI834419 A FI 834419A FI 834419 A FI834419 A FI 834419A FI 81115 C FI81115 C FI 81115C
- Authority
- FI
- Finland
- Prior art keywords
- substituted
- microorganism
- hydroxybutanoic acid
- optically active
- acid derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 58
- 230000008569 process Effects 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 11
- 239000002253 acid Substances 0.000 title description 8
- -1 γ-substituted acetoacetic acid esters Chemical class 0.000 claims description 29
- 244000005700 microbiome Species 0.000 claims description 22
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 17
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims description 16
- 101710088194 Dehydrogenase Proteins 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000000855 fermentation Methods 0.000 claims description 9
- 230000004151 fermentation Effects 0.000 claims description 9
- 230000002255 enzymatic effect Effects 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical class CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 claims description 6
- UCTNTYHJFWMUBD-UHFFFAOYSA-N 4-chloro-3-oxobutanoic acid Chemical compound OC(=O)CC(=O)CCl UCTNTYHJFWMUBD-UHFFFAOYSA-N 0.000 claims description 6
- 241000235070 Saccharomyces Species 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- CJLSDBRIXZFCKV-UHFFFAOYSA-N 4-chloro-3-oxo-n-phenylbutanamide Chemical compound ClCC(=O)CC(=O)NC1=CC=CC=C1 CJLSDBRIXZFCKV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 241000235349 Ascomycota Species 0.000 claims description 2
- 241000228427 Eurotiales Species 0.000 claims description 2
- 241000235388 Mucorales Species 0.000 claims description 2
- 241000235343 Saccharomycetales Species 0.000 claims description 2
- 238000006911 enzymatic reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 35
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 27
- 239000000758 substrate Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 13
- 239000002609 medium Substances 0.000 description 10
- YWUCLFSFZIBCGK-LLVKDONJSA-N octyl (3r)-4-chloro-3-hydroxybutanoate Chemical compound CCCCCCCCOC(=O)C[C@@H](O)CCl YWUCLFSFZIBCGK-LLVKDONJSA-N 0.000 description 10
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 6
- 229960004203 carnitine Drugs 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- PHIQHXFUZVPYII-UHFFFAOYSA-N carnitine Chemical compound C[N+](C)(C)CC(O)CC([O-])=O PHIQHXFUZVPYII-UHFFFAOYSA-N 0.000 description 5
- WMRINGSAVOPXTE-SCSAIBSYSA-N methyl (3r)-4-chloro-3-hydroxybutanoate Chemical compound COC(=O)C[C@@H](O)CCl WMRINGSAVOPXTE-SCSAIBSYSA-N 0.000 description 5
- PLMCCOPFYJURPS-UHFFFAOYSA-N 4-bromo-3-oxobutanoic acid Chemical class OC(=O)CC(=O)CBr PLMCCOPFYJURPS-UHFFFAOYSA-N 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 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 description 4
- 239000008272 agar Substances 0.000 description 4
- 239000008121 dextrose Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- FQDBCBAPZOBXPI-SECBINFHSA-N (3r)-4-chloro-3-hydroxy-n-phenylbutanamide Chemical compound ClC[C@H](O)CC(=O)NC1=CC=CC=C1 FQDBCBAPZOBXPI-SECBINFHSA-N 0.000 description 3
- AFENDNXGAFYKQO-GSVOUGTGSA-N (R)-2-hydroxybutyric acid Chemical class CC[C@@H](O)C(O)=O AFENDNXGAFYKQO-GSVOUGTGSA-N 0.000 description 3
- PHIQHXFUZVPYII-LURJTMIESA-N (S)-carnitine Chemical compound C[N+](C)(C)C[C@@H](O)CC([O-])=O PHIQHXFUZVPYII-LURJTMIESA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- ZAJNMXDBJKCCAT-RXMQYKEDSA-N ethyl (3r)-4-chloro-3-hydroxybutanoate Chemical compound CCOC(=O)C[C@@H](O)CCl ZAJNMXDBJKCCAT-RXMQYKEDSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- HFLMYYLFSNEOOT-UHFFFAOYSA-N methyl 4-chloro-3-oxobutanoate Chemical compound COC(=O)CC(=O)CCl HFLMYYLFSNEOOT-UHFFFAOYSA-N 0.000 description 3
- 230000000813 microbial effect Effects 0.000 description 3
- QVBGSRKQOYZMLR-UHFFFAOYSA-N octyl 4-chloro-3-oxobutanoate Chemical compound CCCCCCCCOC(=O)CC(=O)CCl QVBGSRKQOYZMLR-UHFFFAOYSA-N 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CEEKOEFUYMWDNW-SECBINFHSA-N (3r)-3,4-dihydroxy-n-phenylbutanamide Chemical compound OC[C@H](O)CC(=O)NC1=CC=CC=C1 CEEKOEFUYMWDNW-SECBINFHSA-N 0.000 description 2
- JYUBARICIVVMJB-SECBINFHSA-N (3r)-4-bromo-3-hydroxy-n-phenylbutanamide Chemical compound BrC[C@H](O)CC(=O)NC1=CC=CC=C1 JYUBARICIVVMJB-SECBINFHSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- DASZUXUOOFCMLW-UHFFFAOYSA-N 4-hydroxy-3-oxo-n-phenylbutanamide Chemical compound OCC(=O)CC(=O)NC1=CC=CC=C1 DASZUXUOOFCMLW-UHFFFAOYSA-N 0.000 description 2
- 108010066477 Carnitine O-acetyltransferase Proteins 0.000 description 2
- 102100036357 Carnitine O-acetyltransferase Human genes 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 244000168141 Geotrichum candidum Species 0.000 description 2
- 235000017388 Geotrichum candidum Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 102000004316 Oxidoreductases Human genes 0.000 description 2
- 108090000854 Oxidoreductases Proteins 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 241001149558 Trichoderma virens Species 0.000 description 2
- JXXCENBLGFBQJM-FYZOBXCZSA-N [(2r)-3-carboxy-2-hydroxypropyl]-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)C[C@H](O)CC(O)=O JXXCENBLGFBQJM-FYZOBXCZSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- MUDINVLNUWSPDH-SNVBAGLBSA-N benzyl (3r)-4-bromo-3-hydroxybutanoate Chemical compound BrC[C@H](O)CC(=O)OCC1=CC=CC=C1 MUDINVLNUWSPDH-SNVBAGLBSA-N 0.000 description 2
- AJGRCWAJLBXPIY-SNVBAGLBSA-N benzyl (3r)-4-chloro-3-hydroxybutanoate Chemical compound ClC[C@H](O)CC(=O)OCC1=CC=CC=C1 AJGRCWAJLBXPIY-SNVBAGLBSA-N 0.000 description 2
- AIJGDSYLHMOGOA-UHFFFAOYSA-N benzyl 4-chloro-3-oxobutanoate Chemical compound ClCC(=O)CC(=O)OCC1=CC=CC=C1 AIJGDSYLHMOGOA-UHFFFAOYSA-N 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 230000002906 microbiologic effect Effects 0.000 description 2
- 210000001700 mitochondrial membrane Anatomy 0.000 description 2
- VVLMCVGGCWZLFH-LLVKDONJSA-N octyl (3r)-3,4-dihydroxybutanoate Chemical compound CCCCCCCCOC(=O)C[C@@H](O)CO VVLMCVGGCWZLFH-LLVKDONJSA-N 0.000 description 2
- FAJRBIBGHKCOIX-LLVKDONJSA-N octyl (3r)-3-hydroxy-4-iodobutanoate Chemical compound CCCCCCCCOC(=O)C[C@@H](O)CI FAJRBIBGHKCOIX-LLVKDONJSA-N 0.000 description 2
- GFFSKQYOJURSSC-LLVKDONJSA-N octyl (3r)-4-bromo-3-hydroxybutanoate Chemical compound CCCCCCCCOC(=O)C[C@@H](O)CBr GFFSKQYOJURSSC-LLVKDONJSA-N 0.000 description 2
- PVLXSQWDOVFOND-UHFFFAOYSA-N octyl 4-bromo-3-oxobutanoate Chemical compound CCCCCCCCOC(=O)CC(=O)CBr PVLXSQWDOVFOND-UHFFFAOYSA-N 0.000 description 2
- AZUVSCQANPJNLV-UHFFFAOYSA-N octyl 4-hydroxy-3-oxobutanoate Chemical compound CCCCCCCCOC(=O)CC(=O)CO AZUVSCQANPJNLV-UHFFFAOYSA-N 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- KFHFKBSXONJDPU-ZCFIWIBFSA-N propyl (3r)-4-chloro-3-hydroxybutanoate Chemical compound CCCOC(=O)C[C@@H](O)CCl KFHFKBSXONJDPU-ZCFIWIBFSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 235000013619 trace mineral Nutrition 0.000 description 2
- 239000011573 trace mineral Substances 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- SOCAXRLFGRNEPK-IFZYUDKTSA-N (1r,3s,5r)-2-n-[1-carbamoyl-5-(cyanomethoxy)indol-3-yl]-3-n-[(3-chloro-2-fluorophenyl)methyl]-2-azabicyclo[3.1.0]hexane-2,3-dicarboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)NC1=CN(C2=CC=C(OCC#N)C=C21)C(=O)N)NCC1=CC=CC(Cl)=C1F SOCAXRLFGRNEPK-IFZYUDKTSA-N 0.000 description 1
- AKDAXGMVRMXFOO-GSVOUGTGSA-N (3r)-4-chloro-3-hydroxybutanoic acid Chemical compound ClC[C@H](O)CC(O)=O AKDAXGMVRMXFOO-GSVOUGTGSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AKDAXGMVRMXFOO-UHFFFAOYSA-N 4-chloro-3-hydroxybutanoic acid Chemical class ClCC(O)CC(O)=O AKDAXGMVRMXFOO-UHFFFAOYSA-N 0.000 description 1
- JEZCMVCLPKSUOT-UHFFFAOYSA-N 4-hydroxy-3-oxobutanoic acid Chemical class OCC(=O)CC(O)=O JEZCMVCLPKSUOT-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 241000589220 Acetobacter Species 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241001225321 Aspergillus fumigatus Species 0.000 description 1
- 241000122824 Aspergillus ochraceus Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 241000228339 Byssochlamys nivea Species 0.000 description 1
- LWTLYDKUWQMWER-SSDOTTSWSA-N CCCCOC(=O)C[C@@H](O)CI Chemical compound CCCCOC(=O)C[C@@H](O)CI LWTLYDKUWQMWER-SSDOTTSWSA-N 0.000 description 1
- NYGURNBNQUVIKW-ZCFIWIBFSA-N CCCOC(=O)C[C@@H](O)CI Chemical compound CCCOC(=O)C[C@@H](O)CI NYGURNBNQUVIKW-ZCFIWIBFSA-N 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 241001149472 Clonostachys rosea Species 0.000 description 1
- 241001290628 Cunninghamella echinulata Species 0.000 description 1
- 241000235556 Cunninghamella elegans Species 0.000 description 1
- 241001123634 Dipodascus albidus Species 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 241001149669 Hanseniaspora Species 0.000 description 1
- 244000286779 Hansenula anomala Species 0.000 description 1
- 235000014683 Hansenula anomala Nutrition 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 244000285963 Kluyveromyces fragilis Species 0.000 description 1
- 235000014663 Kluyveromyces fragilis Nutrition 0.000 description 1
- 241000222118 Leptoxyphium fumago Species 0.000 description 1
- 241000235489 Linderina Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000343235 Maso Species 0.000 description 1
- 241000223250 Metarhizium anisopliae Species 0.000 description 1
- 241001450846 Mucor heterogamus Species 0.000 description 1
- 241000907556 Mucor hiemalis Species 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 240000000064 Penicillium roqueforti Species 0.000 description 1
- 235000002233 Penicillium roqueforti Nutrition 0.000 description 1
- 241000364057 Peoria Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 241000235648 Pichia Species 0.000 description 1
- 240000005384 Rhizopus oryzae Species 0.000 description 1
- 235000013752 Rhizopus oryzae Nutrition 0.000 description 1
- 241000223254 Rhodotorula mucilaginosa Species 0.000 description 1
- 241001030146 Rhodotorula sp. Species 0.000 description 1
- 241000825258 Scopulariopsis brevicaulis Species 0.000 description 1
- 241001136496 Talaromyces islandicus Species 0.000 description 1
- 241000006364 Torula Species 0.000 description 1
- 241000223261 Trichoderma viride Species 0.000 description 1
- 241000750042 Vini Species 0.000 description 1
- 241001193070 Wickerhamomyces subpelliculosus Species 0.000 description 1
- 241000235015 Yarrowia lipolytica Species 0.000 description 1
- 241000235017 Zygosaccharomyces Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002948 appetite stimulant Substances 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 229940091771 aspergillus fumigatus Drugs 0.000 description 1
- VYFQKXWCCFQFML-UHFFFAOYSA-N benzyl 4-bromo-3-oxobutanoate Chemical compound BrCC(=O)CC(=O)OCC1=CC=CC=C1 VYFQKXWCCFQFML-UHFFFAOYSA-N 0.000 description 1
- 239000013060 biological fluid Substances 0.000 description 1
- 230000001851 biosynthetic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- KUWKPNMTVKBQTH-SSDOTTSWSA-N butyl (3R)-4-chloro-3-hydroxybutanoate Chemical compound CCCCOC(=O)C[C@@H](O)CCl KUWKPNMTVKBQTH-SSDOTTSWSA-N 0.000 description 1
- KARCVSXXFQZRRC-UHFFFAOYSA-N butyl 4-chloro-3-oxobutanoate Chemical compound CCCCOC(=O)CC(=O)CCl KARCVSXXFQZRRC-UHFFFAOYSA-N 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- AGNNSVUTUUGMQD-CYBMUJFWSA-N decyl (3r)-3-hydroxy-4-iodobutanoate Chemical compound CCCCCCCCCCOC(=O)C[C@@H](O)CI AGNNSVUTUUGMQD-CYBMUJFWSA-N 0.000 description 1
- OMVGVLDYXKQAIP-CYBMUJFWSA-N decyl (3r)-4-chloro-3-hydroxybutanoate Chemical compound CCCCCCCCCCOC(=O)C[C@@H](O)CCl OMVGVLDYXKQAIP-CYBMUJFWSA-N 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 230000008773 effect on children Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- SMWBHOKQXGBYJN-RXMQYKEDSA-N ethyl (3r)-3-hydroxy-4-iodobutanoate Chemical compound CCOC(=O)C[C@@H](O)CI SMWBHOKQXGBYJN-RXMQYKEDSA-N 0.000 description 1
- OHLRLMWUFVDREV-UHFFFAOYSA-N ethyl 4-chloro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CCl OHLRLMWUFVDREV-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 210000005003 heart tissue Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- ZUGINIDGORHHAO-SNVBAGLBSA-N heptyl (3r)-3-hydroxy-4-iodobutanoate Chemical compound CCCCCCCOC(=O)C[C@@H](O)CI ZUGINIDGORHHAO-SNVBAGLBSA-N 0.000 description 1
- VUKJOZYOTKSXFI-SNVBAGLBSA-N heptyl (3r)-4-chloro-3-hydroxybutanoate Chemical compound CCCCCCCOC(=O)C[C@@H](O)CCl VUKJOZYOTKSXFI-SNVBAGLBSA-N 0.000 description 1
- NVJOLYWXQGQGQE-SECBINFHSA-N hexyl (3r)-3-hydroxy-4-iodobutanoate Chemical compound CCCCCCOC(=O)C[C@@H](O)CI NVJOLYWXQGQGQE-SECBINFHSA-N 0.000 description 1
- UOWKLNZUDOURHW-SECBINFHSA-N hexyl (3r)-4-chloro-3-hydroxybutanoate Chemical compound CCCCCCOC(=O)C[C@@H](O)CCl UOWKLNZUDOURHW-SECBINFHSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- AMCCREBZBZYJDT-SCSAIBSYSA-N methyl (3r)-3-hydroxy-4-iodobutanoate Chemical compound COC(=O)C[C@@H](O)CI AMCCREBZBZYJDT-SCSAIBSYSA-N 0.000 description 1
- 210000001589 microsome Anatomy 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 230000002438 mitochondrial effect Effects 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- BVCKRHMKKUQVAA-UHFFFAOYSA-N propyl 4-chloro-3-oxobutanoate Chemical compound CCCOC(=O)CC(=O)CCl BVCKRHMKKUQVAA-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 239000012064 sodium phosphate buffer Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000011924 stereoselective hydrogenation Methods 0.000 description 1
- 238000011916 stereoselective reduction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/0004—Oxidoreductases (1.)
- C12N9/0006—Oxidoreductases (1.) acting on CH-OH groups as donors (1.1)
-
- 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
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/42—Hydroxy-carboxylic acids
-
- 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
- C12P7/62—Carboxylic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/447,171 US4642290A (en) | 1982-12-06 | 1982-12-06 | Process for preparing a compound for use in the production of L-carnitine |
US44717182 | 1982-12-06 | ||
US54495783A | 1983-10-24 | 1983-10-24 | |
US54495783 | 1983-10-24 |
Publications (4)
Publication Number | Publication Date |
---|---|
FI834419A0 FI834419A0 (fi) | 1983-12-02 |
FI834419L FI834419L (fi) | 1984-06-07 |
FI81115B FI81115B (fi) | 1990-05-31 |
FI81115C true FI81115C (fi) | 1990-09-10 |
Family
ID=27034888
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI834419A FI81115C (fi) | 1982-12-06 | 1983-12-02 | Foerfarande foer framstaellning av optiskt aktiva -substituerade -hydroxibutansyraderivat. |
Country Status (23)
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DK544284A (da) * | 1983-12-06 | 1985-06-07 | Hoffmann La Roche | Fremgangsmaade til fremstilling af optisk aktive propionsyrederivater |
IT1181908B (it) * | 1984-07-12 | 1987-09-30 | Debi Derivati Biologici | Procedimento per la preparazione di l-carnitina |
IT1181812B (it) * | 1984-07-27 | 1987-09-30 | Sigma Tau Ind Farmaceuti | Procedimento per la preparazione dell'acido gamma-dimetilammino l-beta-idrossibutirrico |
IT1190358B (it) * | 1985-05-24 | 1988-02-16 | Sclavo Spa | Procedimento per la preparazione di l-carnitina |
JPS62126997A (ja) * | 1985-11-28 | 1987-06-09 | Nippon Synthetic Chem Ind Co Ltd:The | 光学活性のγ−ハロ−βヒドロキシ酪酸エステルの製造法 |
IT1189070B (it) * | 1986-03-14 | 1988-01-28 | Donegani Guido Ist | Processo per la preparazione della l(-)-carnitina cloruro a partire da esteri 3,4-epossibutirrici |
JPH0678277B2 (ja) * | 1988-02-19 | 1994-10-05 | 高砂香料工業株式会社 | 光学活性アルコールおよびその誘導体の製造方法 |
JP2939646B2 (ja) * | 1990-07-17 | 1999-08-25 | チッソ株式会社 | 4―置換―2―ヒドロキシブタン酸エステルおよび製造法 |
US5215919A (en) * | 1991-02-25 | 1993-06-01 | Takeda Chemical Industries, Ltd. | Process for producing optically active 2-hydroxycycloalkanecarboxylic acid esters using microbially derived reductase |
US5324662A (en) | 1992-05-15 | 1994-06-28 | E. R. Squibb & Sons, Inc. | Stereoselective microbial or enzymatic reduction of 3,5-dioxo esters to 3-hydroxy-5-oxo, 3-oxo-5-hydroxy, and 3,5-dihydroxy esters |
JP3155107B2 (ja) * | 1993-01-12 | 2001-04-09 | ダイセル化学工業株式会社 | 光学活性4−ハロ−3−ヒドロキシ酪酸エステルの製造方法 |
JP2000189170A (ja) | 1998-05-08 | 2000-07-11 | Daicel Chem Ind Ltd | 光学活性4―ハロ―3―ヒドロキシ酪酸エステルの製造方法 |
HUP0101122A3 (en) | 1998-08-05 | 2006-02-28 | Kaneka Corp | Process for the preparation of optically active 2-[6-(hydroxymethyl)-1,3-dioxan-4-yl]acetic acid derivatives |
WO2004015132A2 (en) * | 2002-08-09 | 2004-02-19 | Codexis, Inc. | Enzymatic processes for the production of 4-substituted 3-hydroxybutyric acid derivatives |
DE10315760A1 (de) * | 2003-04-07 | 2004-10-21 | Basf Ag | L-Carnitin Dehydrogenasen, deren Derivate und ein Verfahren zur Herstellung von substituierten (S)-Alkanolen |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3931410A (en) * | 1974-02-28 | 1976-01-06 | The Upjohn Company | Composition and method of use |
CH589604A5 (enrdf_load_html_response) * | 1974-04-26 | 1977-07-15 | Lonza Ag | |
JPS5139634A (en) * | 1974-09-27 | 1976-04-02 | Ono Pharmaceutical Co | Ganma amino beeta hidorokishibutansananirido no seizoho |
JPS6017776B2 (ja) * | 1979-11-07 | 1985-05-07 | 電気化学工業株式会社 | γ−クロロ−β−ヒドロキシ酪酸アルキルエステルの製法 |
JPS5950661B2 (ja) * | 1980-07-28 | 1984-12-10 | 電気化学工業株式会社 | γ−アミノ−β−ヒドロキシ酪酸の製造法 |
JPS5950663B2 (ja) * | 1981-04-28 | 1984-12-10 | 電気化学工業株式会社 | γ−アミノ−β−ヒドロキシ酪酸の製造法 |
-
1983
- 1983-11-22 IE IE2732/83A patent/IE56322B1/en not_active IP Right Cessation
- 1983-11-28 AU AU21758/83A patent/AU566906B2/en not_active Ceased
- 1983-11-29 CA CA000442170A patent/CA1225956A/en not_active Expired
- 1983-11-30 IL IL8370352A patent/IL70352A/xx not_active IP Right Cessation
- 1983-12-01 GR GR73128A patent/GR78767B/el unknown
- 1983-12-02 FI FI834419A patent/FI81115C/fi not_active IP Right Cessation
- 1983-12-02 CH CH6448/83A patent/CH661498A5/it not_active IP Right Cessation
- 1983-12-05 GB GB08332359A patent/GB2132614B/en not_active Expired
- 1983-12-05 AT AT4237/83A patent/AT393136B/de not_active IP Right Cessation
- 1983-12-05 ES ES83527807A patent/ES8601305A1/es not_active Expired
- 1983-12-05 PH PH29928A patent/PH20456A/en unknown
- 1983-12-05 DK DK559283A patent/DK163917C/da not_active IP Right Cessation
- 1983-12-05 NO NO834461A patent/NO159291C/no unknown
- 1983-12-05 LU LU85115A patent/LU85115A1/fr unknown
- 1983-12-05 IT IT8324018A patent/IT1167289B/it active
- 1983-12-05 SE SE8306714A patent/SE455501B/sv not_active IP Right Cessation
- 1983-12-06 PT PT77780A patent/PT77780B/pt not_active IP Right Cessation
- 1983-12-06 KR KR1019830005765A patent/KR840008165A/ko not_active Ceased
- 1983-12-06 DE DE3344085A patent/DE3344085C2/de not_active Expired - Fee Related
- 1983-12-06 FR FR8319505A patent/FR2537130B1/fr not_active Expired
- 1983-12-06 NL NL8304190A patent/NL8304190A/nl not_active Application Discontinuation
- 1983-12-06 TR TR10354/83A patent/TR23136A/xx unknown
-
1993
- 1993-09-01 JP JP21771093A patent/JPH0767674A/ja active Pending
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
FI81115C (fi) | Foerfarande foer framstaellning av optiskt aktiva -substituerade -hydroxibutansyraderivat. | |
AU2009344282B2 (en) | Process for the preparation of (3R)-hydroxybutyl (3R)-hydroxybutyrate by enzymatic enantioselective reduction employing Lactobacillus brevis alcohol dehydrogenase | |
US6001615A (en) | Enzymatic reduction of ketone groups in 6-cyano-3,5-dihydroxy-hexanoic alkyl ester | |
US4857468A (en) | Process for preparing optically active 2-halo-1-phenyl ethanol | |
US4642290A (en) | Process for preparing a compound for use in the production of L-carnitine | |
US4710468A (en) | Process for preparing L-carnitine and chemical intermediates employed therein | |
JP2002535977A5 (enrdf_load_html_response) | ||
Buisson et al. | A study of the stereocontrolled reduction of aliphatic β-ketoesters by Geotrichum candidum | |
JP3794702B2 (ja) | キラル−α−第3級カルボン酸エステルの酵素的調製法 | |
CA2116003C (en) | Arylalkanoic acid resolution | |
CA1239361A (en) | METHOD OF PREPARING D(-)-.beta.-HYDROXYISOBUTYRIC ACID BY FERMENTATION | |
JP3941184B2 (ja) | 光学活性1−アシロキシ−3−クロロ−2−プロパノール、及び光学活性3−クロロ−1,2−プロパンジオールの製造法 | |
KR100221357B1 (ko) | 신규 효모균주 피키아 시페라이 dscc 7-25의 발효 최적화를 통한 고효율 스핑고리피드의 제조방법 | |
US6214610B1 (en) | Process for the preparation of optically active N-benzyl-3-pyrrolidinol | |
US4310635A (en) | Fermentative production of D(-)-β-hydroxyisobutyric acid | |
US20020160398A1 (en) | Chlorohydroxyacetone derivative and process for producing optically active chloropropanediol derivative from the same | |
US4981794A (en) | Method of preparing D(-)-β-hydroxyisobutyric acid by fermentation | |
JP2981250B2 (ja) | D―パントテノニトリルの製造法 | |
Matzinger et al. | Asymmetric microbial reduction of ethyl and isoprophyl α, 1, 3-trioxo-2-isoindolinebutyrate | |
JPS60153797A (ja) | メバロン酸の発酵生産法 | |
JPH02227085A (ja) | D―パントテン酸エステルの製造法 | |
WO2001057229A1 (fr) | Procede de production d'esters optiquement actifs de l'acide 4-benzyloxy-3-hydroxybutirique | |
JP2002095495A (ja) | 光学活性アミノアルコール誘導体の製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM | Patent lapsed | ||
MM | Patent lapsed |
Owner name: SIGMA-TAU INDUSTRIE FARMACEUTICHE |