CH661498A5 - Intermedi chimici otticamente attivi utili per la produzione di l-carnitina e procedimenti per la loro preparazione. - Google Patents
Intermedi chimici otticamente attivi utili per la produzione di l-carnitina e procedimenti per la loro preparazione. Download PDFInfo
- Publication number
- CH661498A5 CH661498A5 CH6448/83A CH644883A CH661498A5 CH 661498 A5 CH661498 A5 CH 661498A5 CH 6448/83 A CH6448/83 A CH 6448/83A CH 644883 A CH644883 A CH 644883A CH 661498 A5 CH661498 A5 CH 661498A5
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- CH
- Switzerland
- Prior art keywords
- carbon atoms
- radicals
- substituted
- compound according
- acid
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- 238000000034 method Methods 0.000 title claims description 62
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 title description 35
- 239000000543 intermediate Substances 0.000 title description 3
- 239000000126 substance Substances 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- -1 benzyl ester Chemical class 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 230000008569 process Effects 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 20
- 244000005700 microbiome Species 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 15
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 11
- 101710088194 Dehydrogenase Proteins 0.000 claims description 11
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical class 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 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 230000002255 enzymatic effect Effects 0.000 claims description 8
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 claims description 6
- 241000235070 Saccharomyces Species 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- WHBMMWSBFZVSSR-GSVOUGTGSA-N (R)-3-hydroxybutyric acid Chemical group C[C@@H](O)CC(O)=O WHBMMWSBFZVSSR-GSVOUGTGSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 150000004729 acetoacetic acid derivatives Chemical class 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 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
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical class OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000002071 phenylalkoxy group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 36
- 239000000047 product Substances 0.000 description 21
- 239000000758 substrate Substances 0.000 description 18
- AFENDNXGAFYKQO-GSVOUGTGSA-N (R)-2-hydroxybutyric acid Chemical compound CC[C@@H](O)C(O)=O AFENDNXGAFYKQO-GSVOUGTGSA-N 0.000 description 16
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- AKDAXGMVRMXFOO-GSVOUGTGSA-N (3r)-4-chloro-3-hydroxybutanoic acid Chemical compound ClC[C@H](O)CC(O)=O AKDAXGMVRMXFOO-GSVOUGTGSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- YWUCLFSFZIBCGK-LLVKDONJSA-N octyl (3r)-4-chloro-3-hydroxybutanoate Chemical compound CCCCCCCCOC(=O)C[C@@H](O)CCl YWUCLFSFZIBCGK-LLVKDONJSA-N 0.000 description 8
- 229910001868 water Inorganic materials 0.000 description 8
- WGNSGQNASYNCBU-GSVOUGTGSA-N (3r)-4-bromo-3-hydroxybutanoic acid Chemical class BrC[C@H](O)CC(O)=O WGNSGQNASYNCBU-GSVOUGTGSA-N 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 229960004203 carnitine Drugs 0.000 description 7
- 229920001817 Agar Polymers 0.000 description 6
- 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
- 239000008272 agar Substances 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 150000003931 anilides Chemical class 0.000 description 5
- DZAIOXUZHHTJKN-GSVOUGTGSA-N (3r)-3,4-dihydroxybutanoic acid Chemical compound OC[C@H](O)CC(O)=O DZAIOXUZHHTJKN-GSVOUGTGSA-N 0.000 description 4
- PHIQHXFUZVPYII-LURJTMIESA-N (S)-carnitine Chemical compound C[N+](C)(C)C[C@@H](O)CC([O-])=O PHIQHXFUZVPYII-LURJTMIESA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- PHIQHXFUZVPYII-UHFFFAOYSA-N carnitine Chemical compound C[N+](C)(C)CC(O)CC([O-])=O PHIQHXFUZVPYII-UHFFFAOYSA-N 0.000 description 4
- 239000008121 dextrose Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000000855 fermentation Methods 0.000 description 4
- 230000004151 fermentation Effects 0.000 description 4
- 238000011534 incubation Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 235000009518 sodium iodide Nutrition 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 150000004668 long chain fatty acids Chemical class 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
- 210000003470 mitochondria Anatomy 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- CJLSDBRIXZFCKV-UHFFFAOYSA-N 4-chloro-3-oxo-n-phenylbutanamide Chemical compound ClCC(=O)CC(=O)NC1=CC=CC=C1 CJLSDBRIXZFCKV-UHFFFAOYSA-N 0.000 description 2
- UCTNTYHJFWMUBD-UHFFFAOYSA-N 4-chloro-3-oxobutanoic acid Chemical compound OC(=O)CC(=O)CCl UCTNTYHJFWMUBD-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-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
- 244000168141 Geotrichum candidum Species 0.000 description 2
- 235000017388 Geotrichum candidum Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 229960001413 acetanilide Drugs 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
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- 230000015572 biosynthetic process Effects 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
- 238000004587 chromatography analysis Methods 0.000 description 2
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- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZAJNMXDBJKCCAT-RXMQYKEDSA-N ethyl (3r)-4-chloro-3-hydroxybutanoate Chemical compound CCOC(=O)C[C@@H](O)CCl ZAJNMXDBJKCCAT-RXMQYKEDSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
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- 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
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-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
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- 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
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- 241000228339 Byssochlamys nivea Species 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
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- 241000222122 Candida albicans Species 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
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- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
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- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 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
- 239000012458 free base Substances 0.000 description 1
- 235000012490 fresh bread Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000001963 growth medium Substances 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
- 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
- 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
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 229910000357 manganese(II) sulfate Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- WMRINGSAVOPXTE-SCSAIBSYSA-N methyl (3r)-4-chloro-3-hydroxybutanoate Chemical compound COC(=O)C[C@@H](O)CCl WMRINGSAVOPXTE-SCSAIBSYSA-N 0.000 description 1
- 230000037230 mobility Effects 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- 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 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- KFHFKBSXONJDPU-ZCFIWIBFSA-N propyl (3r)-4-chloro-3-hydroxybutanoate Chemical compound CCCOC(=O)C[C@@H](O)CCl KFHFKBSXONJDPU-ZCFIWIBFSA-N 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011937 reductive transformation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 239000012064 sodium phosphate buffer Substances 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
- 238000003756 stirring Methods 0.000 description 1
- 239000006228 supernatant Substances 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
- 239000010409 thin film Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 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)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| 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 |
| US54495783A | 1983-10-24 | 1983-10-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH661498A5 true CH661498A5 (it) | 1987-07-31 |
Family
ID=27034888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6448/83A CH661498A5 (it) | 1982-12-06 | 1983-12-02 | Intermedi chimici otticamente attivi utili per la produzione di l-carnitina e procedimenti per la loro preparazione. |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPH0767674A (cs) |
| KR (1) | KR840008165A (cs) |
| AT (1) | AT393136B (cs) |
| AU (1) | AU566906B2 (cs) |
| CA (1) | CA1225956A (cs) |
| CH (1) | CH661498A5 (cs) |
| DE (1) | DE3344085C2 (cs) |
| DK (1) | DK163917C (cs) |
| ES (1) | ES527807A0 (cs) |
| FI (1) | FI81115C (cs) |
| FR (1) | FR2537130B1 (cs) |
| GB (1) | GB2132614B (cs) |
| GR (1) | GR78767B (cs) |
| IE (1) | IE56322B1 (cs) |
| IL (1) | IL70352A (cs) |
| IT (1) | IT1167289B (cs) |
| LU (1) | LU85115A1 (cs) |
| NL (1) | NL8304190A (cs) |
| NO (1) | NO159291C (cs) |
| PH (1) | PH20456A (cs) |
| PT (1) | PT77780B (cs) |
| SE (1) | SE455501B (cs) |
| TR (1) | TR23136A (cs) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0144832A3 (de) * | 1983-12-06 | 1987-01-21 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Verfahren zur Herstellung optisch aktiver, alpha-substituierter 3-Hydroxypropionsäurederivate |
| 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 |
| ATE486068T1 (de) | 1998-08-05 | 2010-11-15 | Kaneka Corp | Verfahren zur herstellung optisch aktiver 2-ä6- (hydroxymethyl)-1,3-dioxan-4-ylü-essigsäure- derivate |
| 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 (cs) * | 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 SE SE8306714A patent/SE455501B/sv not_active IP Right Cessation
- 1983-12-05 NO NO834461A patent/NO159291C/no unknown
- 1983-12-05 AT AT4237/83A patent/AT393136B/de not_active IP Right Cessation
- 1983-12-05 IT IT8324018A patent/IT1167289B/it active
- 1983-12-05 ES ES83527807A patent/ES527807A0/es active Granted
- 1983-12-05 PH PH29928A patent/PH20456A/en unknown
- 1983-12-05 GB GB08332359A patent/GB2132614B/en not_active Expired
- 1983-12-05 LU LU85115A patent/LU85115A1/fr unknown
- 1983-12-05 DK DK559283A patent/DK163917C/da not_active IP Right Cessation
- 1983-12-06 KR KR1019830005765A patent/KR840008165A/ko not_active Ceased
- 1983-12-06 PT PT77780A patent/PT77780B/pt not_active IP Right Cessation
- 1983-12-06 FR FR8319505A patent/FR2537130B1/fr not_active Expired
- 1983-12-06 DE DE3344085A patent/DE3344085C2/de not_active Expired - Fee Related
- 1983-12-06 TR TR10354/83A patent/TR23136A/xx unknown
- 1983-12-06 NL NL8304190A patent/NL8304190A/nl not_active Application Discontinuation
-
1993
- 1993-09-01 JP JP21771093A patent/JPH0767674A/ja active Pending
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| PL | Patent ceased | ||
| PL | Patent ceased |