NL1019416C2 - Werkwijze voor het bereiden van een enantiomeer verrijkt a-aminozuur. - Google Patents
Werkwijze voor het bereiden van een enantiomeer verrijkt a-aminozuur. Download PDFInfo
- Publication number
- NL1019416C2 NL1019416C2 NL1019416A NL1019416A NL1019416C2 NL 1019416 C2 NL1019416 C2 NL 1019416C2 NL 1019416 A NL1019416 A NL 1019416A NL 1019416 A NL1019416 A NL 1019416A NL 1019416 C2 NL1019416 C2 NL 1019416C2
- Authority
- NL
- Netherlands
- Prior art keywords
- amino acid
- carbamoyl
- carbamoylase
- conversion
- preparation
- Prior art date
Links
- 235000008206 alpha-amino acids Nutrition 0.000 title claims description 19
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 title description 10
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 24
- 108090000790 Enzymes Proteins 0.000 claims description 22
- 102000004190 Enzymes Human genes 0.000 claims description 22
- 102100036238 Dihydropyrimidinase Human genes 0.000 claims description 17
- 108091022884 dihydropyrimidinase Proteins 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- 235000001014 amino acid Nutrition 0.000 claims description 15
- 150000001413 amino acids Chemical class 0.000 claims description 13
- 108010000622 N-carbamoyl-D-amino acid amidohydrolase Proteins 0.000 claims description 12
- 150000001371 alpha-amino acids Chemical class 0.000 claims description 9
- 108010088443 hydantoin racemase Proteins 0.000 claims description 9
- 238000005580 one pot reaction Methods 0.000 claims description 7
- 108010011945 N-carbamoyl-L-amino-acid hydrolase Proteins 0.000 claims description 6
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 5
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 4
- 229930182817 methionine Natural products 0.000 claims description 4
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 3
- 229940024606 amino acid Drugs 0.000 description 63
- 150000001469 hydantoins Chemical class 0.000 description 15
- 230000000694 effects Effects 0.000 description 12
- 229940091173 hydantoin Drugs 0.000 description 12
- 150000007650 D alpha amino acids Chemical class 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000007649 L alpha amino acids Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 241000589155 Agrobacterium tumefaciens Species 0.000 description 4
- ROHFNLRQFUQHCH-RXMQYKEDSA-N D-leucine Chemical compound CC(C)C[C@@H](N)C(O)=O ROHFNLRQFUQHCH-RXMQYKEDSA-N 0.000 description 4
- 229930182819 D-leucine Natural products 0.000 description 4
- 229910003944 H3 PO4 Inorganic materials 0.000 description 4
- 239000006285 cell suspension Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- JUIBQJHHPDRAGP-YFKPBYRVSA-N (2s)-2-(carbamoylamino)-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NC(N)=O JUIBQJHHPDRAGP-YFKPBYRVSA-N 0.000 description 3
- 229960003136 leucine Drugs 0.000 description 3
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- 235000006109 methionine Nutrition 0.000 description 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 2
- FFEARJCKVFRZRR-SCSAIBSYSA-N D-methionine Chemical compound CSCC[C@@H](N)C(O)=O FFEARJCKVFRZRR-SCSAIBSYSA-N 0.000 description 2
- 229930182818 D-methionine Natural products 0.000 description 2
- 241000588697 Enterobacter cloacae Species 0.000 description 2
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- 241001468261 Lysinibacillus macroides Species 0.000 description 2
- DEWDMTSMCKXBNP-BYPYZUCNSA-N N-carbamoyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC(N)=O DEWDMTSMCKXBNP-BYPYZUCNSA-N 0.000 description 2
- 241000157908 Paenarthrobacter aurescens Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000589774 Pseudomonas sp. Species 0.000 description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 2
- 239000004473 Threonine Substances 0.000 description 2
- 125000000539 amino acid group Chemical group 0.000 description 2
- 235000009582 asparagine Nutrition 0.000 description 2
- 229960001230 asparagine Drugs 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000018417 cysteine Nutrition 0.000 description 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 235000004554 glutamine Nutrition 0.000 description 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 2
- 235000005772 leucine Nutrition 0.000 description 2
- 235000018977 lysine Nutrition 0.000 description 2
- 230000006340 racemization Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 235000004400 serine Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 235000008521 threonine Nutrition 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- DEWDMTSMCKXBNP-UHFFFAOYSA-N 2-(carbamoylamino)-4-methylsulfanylbutanoic acid Chemical compound CSCCC(C(O)=O)NC(N)=O DEWDMTSMCKXBNP-UHFFFAOYSA-N 0.000 description 1
- 241000607534 Aeromonas Species 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 241000186063 Arthrobacter Species 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 241000186146 Brevibacterium Species 0.000 description 1
- 241000589565 Flavobacterium Species 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- 239000004395 L-leucine Substances 0.000 description 1
- 235000019454 L-leucine Nutrition 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- 241000192041 Micrococcus Species 0.000 description 1
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 description 1
- 241001057811 Paracoccus <mealybug> Species 0.000 description 1
- 241000235648 Pichia Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000607720 Serratia Species 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 235000009697 arginine Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000013477 citrulline Nutrition 0.000 description 1
- 229960002173 citrulline Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000012239 gene modification Methods 0.000 description 1
- 230000005017 genetic modification Effects 0.000 description 1
- 235000013617 genetically modified food Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 235000014304 histidine Nutrition 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 235000014705 isoleucine Nutrition 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- VWHRYODZTDMVSS-QMMMGPOBSA-N m-fluoro-L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC(F)=C1 VWHRYODZTDMVSS-QMMMGPOBSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- 239000000813 peptide hormone Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 235000008729 phenylalanine Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000002708 random mutagenesis Methods 0.000 description 1
- 238000002741 site-directed mutagenesis Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 235000002374 tyrosine Nutrition 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 235000014393 valine Nutrition 0.000 description 1
- 239000002132 β-lactam antibiotic Substances 0.000 description 1
- 229940124586 β-lactam antibiotics Drugs 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/08—Lysine; Diaminopimelic acid; Threonine; Valine
-
- 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/06—Alanine; Leucine; Isoleucine; Serine; Homoserine
-
- 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/12—Methionine; Cysteine; Cystine
-
- 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/22—Tryptophan; Tyrosine; Phenylalanine; 3,4-Dihydroxyphenylalanine
- C12P13/222—Phenylalanine
-
- 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
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures
- C12P41/009—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures by reactions involving hydantoins or carbamoylamino compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Analytical Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1019416A NL1019416C2 (nl) | 2001-11-23 | 2001-11-23 | Werkwijze voor het bereiden van een enantiomeer verrijkt a-aminozuur. |
| JP2003545827A JP2005509439A (ja) | 2001-11-23 | 2002-11-22 | エナンチオマーに富むα−アミノ酸の製造法 |
| CN 02823310 CN1592789A (zh) | 2001-11-23 | 2002-11-22 | 对映异构体富集的α－氨基酸的制备方法 |
| PCT/NL2002/000758 WO2003044206A2 (en) | 2001-11-23 | 2002-11-22 | Process for the preparation of an enantiomerically enriched a-amino acid |
| EP02783830A EP1446492A2 (en) | 2001-11-23 | 2002-11-22 | Process for the preparation of an enantiomerically enriched a-amino acid |
| AU2002347652A AU2002347652A1 (en) | 2001-11-23 | 2002-11-22 | Process for the preparation of an enantiomerically enriched a-amino acid |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1019416A NL1019416C2 (nl) | 2001-11-23 | 2001-11-23 | Werkwijze voor het bereiden van een enantiomeer verrijkt a-aminozuur. |
| NL1019416 | 2001-11-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL1019416C2 true NL1019416C2 (nl) | 2003-06-02 |
Family
ID=19774336
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL1019416A NL1019416C2 (nl) | 2001-11-23 | 2001-11-23 | Werkwijze voor het bereiden van een enantiomeer verrijkt a-aminozuur. |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1446492A2 (enrdf_load_stackoverflow) |
| JP (1) | JP2005509439A (enrdf_load_stackoverflow) |
| CN (1) | CN1592789A (enrdf_load_stackoverflow) |
| AU (1) | AU2002347652A1 (enrdf_load_stackoverflow) |
| NL (1) | NL1019416C2 (enrdf_load_stackoverflow) |
| WO (1) | WO2003044206A2 (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1928103B (zh) * | 2006-08-30 | 2010-09-01 | 石家庄中天生物技术有限责任公司 | 采用非均相酶催化法生产d-对羟基苯甘氨酸的方法 |
| CN106676157A (zh) * | 2017-02-20 | 2017-05-17 | 南华大学 | 军团菌菌体制备氨基酸构型转换试剂的应用 |
| CN110714035A (zh) * | 2019-11-15 | 2020-01-21 | 江南大学 | 一种级联反应制备d-脂肪族氨基酸的方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0152977A1 (en) * | 1984-02-02 | 1985-08-28 | SCLAVO S.p.A. | Process for the preparation of L-alpha-aminoacids |
| EP0625571A2 (de) * | 1993-05-19 | 1994-11-23 | Degussa Aktiengesellschaft | Neue Mikroorganismen, deren Verwendung und Verfahren zur Herstellung von L-Alpha-Aminosäuren |
| EP0745678A2 (de) * | 1995-05-30 | 1996-12-04 | Degussa Aktiengesellschaft | Neuer Mikroorganismus, dessen Verwendung und Verfahren zur Herstellung von L-Alpha-Aminosäuren |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1276163B1 (it) * | 1995-11-23 | 1997-10-27 | Eniricerche Spa | Procedimento migliorato per la preparazione di d-alfa-amminoacidi |
| NL1017250C1 (nl) * | 2001-01-31 | 2002-08-01 | Dsm Nv | Werkwijze voor de bereiding van enantiomeer verrijkte aminozuren. |
-
2001
- 2001-11-23 NL NL1019416A patent/NL1019416C2/nl not_active IP Right Cessation
-
2002
- 2002-11-22 JP JP2003545827A patent/JP2005509439A/ja active Pending
- 2002-11-22 EP EP02783830A patent/EP1446492A2/en not_active Withdrawn
- 2002-11-22 AU AU2002347652A patent/AU2002347652A1/en not_active Abandoned
- 2002-11-22 WO PCT/NL2002/000758 patent/WO2003044206A2/en active Application Filing
- 2002-11-22 CN CN 02823310 patent/CN1592789A/zh active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0152977A1 (en) * | 1984-02-02 | 1985-08-28 | SCLAVO S.p.A. | Process for the preparation of L-alpha-aminoacids |
| EP0625571A2 (de) * | 1993-05-19 | 1994-11-23 | Degussa Aktiengesellschaft | Neue Mikroorganismen, deren Verwendung und Verfahren zur Herstellung von L-Alpha-Aminosäuren |
| EP0745678A2 (de) * | 1995-05-30 | 1996-12-04 | Degussa Aktiengesellschaft | Neuer Mikroorganismus, dessen Verwendung und Verfahren zur Herstellung von L-Alpha-Aminosäuren |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003044206A2 (en) | 2003-05-30 |
| WO2003044206A3 (en) | 2003-12-18 |
| AU2002347652A8 (en) | 2003-06-10 |
| AU2002347652A1 (en) | 2003-06-10 |
| CN1592789A (zh) | 2005-03-09 |
| EP1446492A2 (en) | 2004-08-18 |
| JP2005509439A (ja) | 2005-04-14 |
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