UA75331C2 - Method for the preparation of l-phosphinothricines by means of enzymatic transamination with aspartate - Google Patents

Method for the preparation of l-phosphinothricines by means of enzymatic transamination with aspartate Download PDF

Info

Publication number: UA75331C2
Authority: UA; Ukraine
Prior art keywords: acid; aspartate; pyruvate; acceptor; esters
Prior art date: 1999-04-30

Application number

UA2001118183A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Aventis Cropscience Gmbh

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-04-30

Filing date

2000-03-30

Publication date

2006-04-17

2000-03-30 Application filed by Aventis Cropscience Gmbh filed Critical Aventis Cropscience Gmbh

2006-04-17 Publication of UA75331C2 publication Critical patent/UA75331C2/uk

Links

CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 title claims abstract description 23
229940009098 aspartate Drugs 0.000 title claims abstract description 22
238000000034 method Methods 0.000 title claims abstract description 19
238000005891 transamination reaction Methods 0.000 title claims abstract description 15
230000002255 enzymatic effect Effects 0.000 title claims abstract description 13
238000006243 chemical reaction Methods 0.000 claims abstract description 43
102000003929 Transaminases Human genes 0.000 claims abstract description 22
108090000340 Transaminases Proteins 0.000 claims abstract description 22
239000002253 acid Substances 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims description 23
102000004190 Enzymes Human genes 0.000 claims description 21
108090000790 Enzymes Proteins 0.000 claims description 21
102000004625 Aspartate Aminotransferases Human genes 0.000 claims description 17
LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims description 13
108030002081 Aspartate transaminases Proteins 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 9
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 7
108010000700 Acetolactate synthase Proteins 0.000 claims description 6
244000005700 microbiome Species 0.000 claims description 6
239000002689 soil Substances 0.000 claims description 6
150000001408 amides Chemical class 0.000 claims description 5
KHPXUQMNIQBQEV-UHFFFAOYSA-N oxaloacetic acid Chemical compound OC(=O)CC(=O)C(O)=O KHPXUQMNIQBQEV-UHFFFAOYSA-N 0.000 claims description 5
YJTNHDYMQPHXFO-UHFFFAOYSA-N 4-(hydroxymethylphosphinyl)-2-oxobutyric acid Chemical compound CP(O)(=O)CCC(=O)C(O)=O YJTNHDYMQPHXFO-UHFFFAOYSA-N 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
108010011939 Pyruvate Decarboxylase Proteins 0.000 claims description 3
108010042687 Pyruvate Oxidase Proteins 0.000 claims description 3
150000001735 carboxylic acids Chemical class 0.000 claims 3
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 2
WTLNOANVTIKPEE-UHFFFAOYSA-N 2-acetyloxypropanoic acid Chemical compound OC(=O)C(C)OC(C)=O WTLNOANVTIKPEE-UHFFFAOYSA-N 0.000 claims 1
229910019142 PO4 Inorganic materials 0.000 claims 1
238000006911 enzymatic reaction Methods 0.000 claims 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
239000010452 phosphate Substances 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 abstract description 16
238000003786 synthesis reaction Methods 0.000 abstract description 11
229940088598 enzyme Drugs 0.000 description 18
239000000243 solution Substances 0.000 description 13
239000000758 substrate Substances 0.000 description 13
NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 description 10
229940024606 amino acid Drugs 0.000 description 8
235000001014 amino acid Nutrition 0.000 description 8
150000001413 amino acids Chemical class 0.000 description 8
108010003415 Aspartate Aminotransferases Proteins 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000007983 Tris buffer Substances 0.000 description 6
125000003277 amino group Chemical group 0.000 description 6
229930195712 glutamate Natural products 0.000 description 6
239000000203 mixture Substances 0.000 description 6
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
239000000370 acceptor Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
150000004715 keto acids Chemical class 0.000 description 5
239000000047 product Substances 0.000 description 5
235000007682 pyridoxal 5'-phosphate Nutrition 0.000 description 5
239000011589 pyridoxal 5'-phosphate Substances 0.000 description 5
229960001327 pyridoxal phosphate Drugs 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
235000004279 alanine Nutrition 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
235000018102 proteins Nutrition 0.000 description 4
102000004169 proteins and genes Human genes 0.000 description 4
108090000623 proteins and genes Proteins 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000002585 base Substances 0.000 description 3
229940079919 digestives enzyme preparation Drugs 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
239000002609 medium Substances 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
235000003704 aspartic acid Nutrition 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
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 2
239000011942 biocatalyst Substances 0.000 description 2
230000036983 biotransformation Effects 0.000 description 2
239000000872 buffer Substances 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
229960003692 gamma aminobutyric acid Drugs 0.000 description 2
229940093915 gynecological organic acid Drugs 0.000 description 2
230000002363 herbicidal effect Effects 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
239000003864 humus Substances 0.000 description 2
238000011534 incubation Methods 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 description 1
KPGXRSRHYNQIFN-UHFFFAOYSA-L 2-oxoglutarate(2-) Chemical compound [O-]C(=O)CCC(=O)C([O-])=O KPGXRSRHYNQIFN-UHFFFAOYSA-L 0.000 description 1
KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
108010060511 4-Aminobutyrate Transaminase Proteins 0.000 description 1
102100035923 4-aminobutyrate aminotransferase, mitochondrial Human genes 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
241000272194 Ciconiiformes Species 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
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 1
235000010469 Glycine max Nutrition 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
IFILAINTMNFQIX-UHFFFAOYSA-N OCP(=O)CCC(=O)C(O)=O Chemical compound OCP(=O)CCC(=O)C(O)=O IFILAINTMNFQIX-UHFFFAOYSA-N 0.000 description 1
IAJOBQBIJHVGMQ-UHFFFAOYSA-N Phosphinothricin Natural products CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 1
101710098398 Probable alanine aminotransferase, mitochondrial Proteins 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000008272 agar Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
229940088623 biologically active substance Drugs 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000005277 cation exchange chromatography Methods 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
238000004296 chiral HPLC Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
-1 for example Chemical class 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
150000004675 formic acid derivatives Chemical class 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
IAJOBQBIJHVGMQ-BYPYZUCNSA-N glufosinate-P Chemical compound CP(O)(=O)CC[C@H](N)C(O)=O IAJOBQBIJHVGMQ-BYPYZUCNSA-N 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000012528 membrane Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
238000005457 optimization Methods 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229960001639 penicillamine Drugs 0.000 description 1
230000035699 permeability Effects 0.000 description 1
230000008823 permeabilization Effects 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
238000000053 physical method Methods 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
239000002243 precursor Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
238000012545 processing Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
238000004445 quantitative analysis Methods 0.000 description 1
125000001453 quaternary ammonium group Chemical class 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011535 reaction buffer Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
238000005070 sampling Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000012064 sodium phosphate buffer Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000010186 staining Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
238000000825 ultraviolet detection 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids

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Organic Chemistry (AREA)
Chemical & Material Sciences (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)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Enzymes And Modification Thereof (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)

UA2001118183A 1999-04-30 2000-03-30 Method for the preparation of l-phosphinothricines by means of enzymatic transamination with aspartate UA75331C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19919848A DE19919848A1 (de)	1999-04-30	1999-04-30	Verfahren zur Herstellung von L-Phosphinothricin durch enzymatische Transaminierung mit Aspartat
PCT/EP2000/002809 WO2000066760A1 (de)	1999-04-30	2000-03-30	Verfahren zur herstellung von l-phosphinothricin durch enzymatische transaminierung mit aspartat

Publications (1)

Publication Number	Publication Date
UA75331C2 true UA75331C2 (en)	2006-04-17

Family

ID=7906505

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2001118183A UA75331C2 (en)	1999-04-30	2000-03-30	Method for the preparation of l-phosphinothricines by means of enzymatic transamination with aspartate

Country Status (22)

Country	Link
US (1)	US6936444B1 (pl)
EP (1)	EP1177310B1 (pl)
JP (1)	JP2003528572A (pl)
KR (1)	KR100810169B1 (pl)
CN (1)	CN1284858C (pl)
AT (1)	ATE287965T1 (pl)
AU (1)	AU768315B2 (pl)
BR (1)	BR0010199A (pl)
CA (1)	CA2370109C (pl)
CZ (1)	CZ20013901A3 (pl)
DE (2)	DE19919848A1 (pl)
DK (1)	DK1177310T3 (pl)
ES (1)	ES2235865T3 (pl)
HU (1)	HU228395B1 (pl)
IL (2)	IL145925A0 (pl)
MX (1)	MXPA01011016A (pl)
NZ (1)	NZ515088A (pl)
PL (1)	PL202575B1 (pl)
RU (1)	RU2275428C2 (pl)
SK (1)	SK286456B6 (pl)
UA (1)	UA75331C2 (pl)
WO (1)	WO2000066760A1 (pl)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7772426B2 (en)	2005-03-29	2010-08-10	Meiji Seika Kaisha, Ltd.	Method for producing L-2-amino-4-(hydroxymethylphosphinyl)-butanoic acid
EP1818411A1 (en) *	2006-02-13	2007-08-15	Lonza AG	Process for the preparation of optically active chiral amines
WO2007100101A1 (ja) *	2006-03-02	2007-09-07	Meiji Seika Kaisha, Ltd.	アスパラギン酸アミノトランスフェラーゼ遺伝子およびｌ－ホスフィノスリシンの製造方法
BRPI0716080B8 (pt)	2006-09-04	2018-02-14	Meiji Seika Kaisha	processo para produção de ácidos (aminofosfinil) butanóicos oticamente ativos
WO2008035687A1 (en)	2006-09-20	2008-03-27	Meiji Seika Kaisha Ltd.	METHOD FOR PRODUCING PHOSPHORUS-CONTAINING α-AMINO ACID AND PRODUCTION INTERMEDIATE THEREOF
CN101641363A (zh)	2007-03-23	2010-02-03	明治制果株式会社	含磷的α-酮酸的制造方法
HUE052297T2 (hu)	2009-01-08	2021-04-28	Codexis Inc	Transzamináz polipeptidek
JP5707344B2 (ja)	2009-02-26	2015-04-30	コデクシス，インコーポレイテッド	トランスアミナーゼ生体触媒
WO2011005477A1 (en)	2009-06-22	2011-01-13	Codexis, Inc.	Transaminase reactions
US8981142B2 (en)	2010-04-14	2015-03-17	Strategic Enzyme Applications, Inc.	Process of producing phosphinothricin employing nitrilases
HUE038434T2 (hu)	2010-06-17	2018-10-29	Codexis Inc	Biokatalizátorok és módszerek (S)-3(1-aminoetil)-fenol szintéziséhez
EP2606139B1 (en)	2010-08-16	2015-07-15	Codexis, Inc.	Biocatalysts and methods for the synthesis of (1r,2r)-2-(3,4-dimethoxyphenethoxy)cyclohexanamine
CN105603015B (zh) *	2016-01-22	2018-12-11	浙江大学	一种l-草铵膦的生产方法
IL261271B2 (en)	2016-03-02	2025-03-01	Agrimetis Llc	Methods for preparing L-glucosinate
CN106916857B (zh) *	2017-03-09	2019-08-27	浙江大学	一种生产l-草铵膦的方法
CN107119084B (zh) *	2017-03-23	2019-12-17	浙江大学	一种利用转氨酶和乙烯合成酶生产l-草铵膦的方法
CN110343676B (zh)	2018-04-03	2020-06-23	上海弈柯莱生物医药科技有限公司	一种l-谷氨酸脱氢酶突变体及其应用
US12559777B2 (en)	2018-09-05	2026-02-24	Basf Se	Methods for improving yields of L-glufosinate
CN109369711A (zh) *	2018-10-26	2019-02-22	洪湖市泰科技有限公司	一种l-草胺膦关键中间体的合成新方法
CN111019916B (zh)	2018-11-23	2020-12-08	弈柯莱生物科技(上海)股份有限公司	一种d-氨基酸氧化酶突变体及其应用
CN111979208B (zh)	2019-05-23	2023-01-10	弈柯莱生物科技(上海)股份有限公司	一种l-谷氨酸脱氢酶突变体及其应用
CN112725298B (zh)	2020-12-31	2022-12-06	浙江工业大学	一种机器学习基因挖掘方法及氨基转位用草铵膦脱氢酶突变体

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2717440C2 (de)	1976-05-17	1984-04-05	Hoechst Ag, 6230 Frankfurt	Unkrautbekämpfung mit [(3-Amino-3-carboxy)-propyl-1]-methylphosphinsäure-Derivaten
GB2011416B (en)	1977-12-28	1982-10-20	Meiji Seika Kaisha	Herbicidal compositions
HU193902B (en) *	1983-09-01	1987-12-28	Genetics Inst	Process for preparing l-amino acids by means of transamination
US4826766A (en)	1985-09-23	1989-05-02	Genetics Institute, Inc.	Production of amino acids using coupled aminotransferases
EP0533216B1 (de) *	1986-06-04	2000-03-22	Hoechst Schering AgrEvo GmbH	Verfahren zur Herstellung von L-tertiär-Leucin durch Transaminierung
AU599985B2 (en) *	1986-06-09	1990-08-02	Meiji Seika Kaisha Ltd.	New process for the production of L-2-amino-4- (hydroxymethyl-phosphinyl)-butyric acid
DE3818851A1 (de)	1988-06-03	1989-12-14	Hoechst Ag	Neue transaminase, ihre herstellung und ihre verwendung
EP0349965A3 (en) *	1988-07-04	1990-06-13	Meiji Seika Kaisha Ltd.	Novel genes encoding transaminase
DE3932015A1 (de)	1988-12-15	1991-04-04	Hoechst Ag	Gen und genstruktur, codierend fuer eine aminotransferase, mikroorganismen, die dieses gen exprimieren, und transaminierungsverfahren unter verwendung des expressionsprodukts
DE4030578A1 (de) *	1990-09-27	1992-04-16	Hoechst Ag	Verfahren zur herstellung von l-phosphinothricin durch eine gekoppelte enzymatische reaktion
US5962283A (en)	1995-12-07	1999-10-05	Diversa Corporation	Transminases and amnotransferases
US6197558B1 (en) *	1997-05-19	2001-03-06	Nsc Technologies	Transaminase biotransformation process

1999
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RU2275428C2 (ru)	2006-04-27
MXPA01011016A (es)	2002-05-06
HUP0200948A2 (hu)	2002-07-29
ATE287965T1 (de)	2005-02-15
CZ20013901A3 (cs)	2002-02-13
IL145925A0 (en)	2002-07-25
IL145925A (en)	2007-05-15
EP1177310A1 (de)	2002-02-06
EP1177310B1 (de)	2005-01-26
WO2000066760A1 (de)	2000-11-09
DE19919848A1 (de)	2000-11-02
PL353460A1 (pl)	2003-11-17
ES2235865T3 (es)	2005-07-16
HU228395B1 (en)	2013-03-28
DK1177310T3 (da)	2005-04-11
US6936444B1 (en)	2005-08-30
CA2370109A1 (en)	2000-11-09
CN1349561A (zh)	2002-05-15
AU4540800A (en)	2000-11-17
NZ515088A (en)	2003-06-30
BR0010199A (pt)	2002-01-08
PL202575B1 (pl)	2009-07-31
SK15622001A3 (sk)	2002-06-04
KR100810169B1 (ko)	2008-03-06
CA2370109C (en)	2009-07-07
AU768315B2 (en)	2003-12-11
JP2003528572A (ja)	2003-09-30
KR20010112473A (ko)	2001-12-20
CN1284858C (zh)	2006-11-15
SK286456B6 (sk)	2008-10-07
DE50009364D1 (de)	2005-03-03
HUP0200948A3 (en)	2010-01-28

Publication	Publication Date	Title
UA75331C2 (en)	2006-04-17	Method for the preparation of l-phosphinothricines by means of enzymatic transamination with aspartate
Hummel et al.	1987	Isolation of L-phenylalanine dehydrogenase from Rhodococcus sp. M4 and its application for the production of L-phenylalanine
US5981239A (en)	1999-11-09	Synthesis of optically active phenylalanine analogs using Rhodotorula graminis
AU2007294090A1 (en)	2008-03-13	Process for preparation of optically active N-protected 3 -aminopyrrolidine or optically active N-protected 3-aminopiperidine and the corresponding ketones by optical resolution of the racemic amine mixtures employing a bacterial omega-transaminase
WO1989001525A1 (en)	1989-02-23	Process for preparation of organic chemicals
US5108914A (en)	1992-04-28	Process for the synthesis of l-alpha-amino acids
CA2066926A1 (en)	1992-10-27	Process for the separation of the optical isomers of alphasubstituted carboxylic acids
Kato et al.	1993	Enzymatic synthesis of l-β-chloroalanine using amino acid dehydrogenase
JPH10286098A (ja)	1998-10-27	Ｄ−アミノ酸の製造方法、ならびにアミンの製造方法
Tarui et al.	2002	Kinetic resolution of an indan derivative using Bacillus sp. SUI-12: Synthesis of a key intermediate of the melatonin receptor agonist TAK-375
US20060172393A1 (en)	2006-08-03	Process for producing optically active alpha -methylcysteine derivative
EP0315786A1 (en)	1989-05-17	Process for the preparation of a d-alfa-amino acid from the corresponding alfa-keto acid
JP2026511215A (ja)	2026-04-10	Ｌ－グルホシネート又はその塩の調製プロセス
JP2002017386A (ja)	2002-01-22	インドール−３−カルボン酸誘導体の製造法
Boesten et al.	1986	Efficient enzymic production of enantiomerically pure amino acids
JPH06253876A (ja)	1994-09-13	α−メチルベンジルアミンの製造法
JPH05103693A (ja)	1993-04-27	光学活性アルコールの製造方法
JPH06319588A (ja)	1994-11-22	光学活性なノルスタチン誘導体の製造方法
JPH0446116B2 (pl)	1992-07-28
JP2001314197A (ja)	2001-11-13	光学活性なヒドロキシアルキル−α−アミノカルボン酸の製造方法
JPH02117396A (ja)	1990-05-01	光学活性２−ハロブタン酸の製造法
JPH0391489A (ja)	1991-04-17	Ｌ―セリンの製造法