SK282932B6 - Spôsob enantiomérneho obohacovania zmesi D- a L-treo-2-amino-3- hydroxy-3-fenylpropiónových kyselín - Google Patents

Spôsob enantiomérneho obohacovania zmesi D- a L-treo-2-amino-3- hydroxy-3-fenylpropiónových kyselín Download PDF

Info

Publication number: SK282932B6
Authority: SK; Slovakia
Prior art keywords: threo; hydroxy; amino; hydrogen; mixture
Prior art date: 1991-03-27

Application number

SK912-92A

Other languages

English (en)

Slovak (sk)

Inventor

Andrew L. Zeitlin

Muppala S. Raju

David I. Stirling

Original Assignee

Celgene Corporation

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.)

1991-03-27

Filing date

1992-03-26

Publication date

2003-01-09

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27418304&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SK282932(B6) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1992-03-26 Application filed by Celgene Corporation filed Critical Celgene Corporation

2003-01-09 Publication of SK282932B6 publication Critical patent/SK282932B6/sk

Links

238000000034 method Methods 0.000 title claims abstract description 35
239000000203 mixture Substances 0.000 title claims abstract description 33
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 23
239000001257 hydrogen Substances 0.000 claims abstract description 20
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 11
239000002253 acid Substances 0.000 claims abstract description 8
150000007513 acids Chemical class 0.000 claims abstract description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
150000003839 salts Chemical class 0.000 claims abstract description 7
108010049097 threonine acetaldehyde-lyase Proteins 0.000 claims abstract description 7
150000003862 amino acid derivatives Chemical class 0.000 claims abstract description 5
239000012736 aqueous medium Substances 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
125000006244 carboxylic acid protecting group Chemical group 0.000 claims abstract 2
-1 hydroxy, methoxy, methylsulfonyl Chemical group 0.000 claims description 15
239000011541 reaction mixture Substances 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
239000007795 chemical reaction product Substances 0.000 claims description 4
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
150000003935 benzaldehydes Chemical class 0.000 claims description 3
150000001768 cations Chemical class 0.000 claims description 3
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150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
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239000002904 solvent Substances 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims 2
238000010521 absorption reaction Methods 0.000 claims 1
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238000007614 solvation Methods 0.000 claims 1
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125000003545 alkoxy group Chemical group 0.000 abstract description 3
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230000007017 scission Effects 0.000 description 5
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238000005119 centrifugation Methods 0.000 description 4
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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239000004473 Threonine Substances 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229960003767 alanine Drugs 0.000 description 3
235000004279 alanine Nutrition 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
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238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
238000006911 enzymatic reaction Methods 0.000 description 3
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238000003756 stirring Methods 0.000 description 3
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
AYIRNRDRBQJXIF-NXEZZACHSA-N (-)-Florfenicol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CF)NC(=O)C(Cl)Cl)C=C1 AYIRNRDRBQJXIF-NXEZZACHSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
PSVPUHBSBYJSMQ-UHFFFAOYSA-N 4-methylsulfonylbenzaldehyde Chemical compound CS(=O)(=O)C1=CC=C(C=O)C=C1 PSVPUHBSBYJSMQ-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
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WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
238000004296 chiral HPLC Methods 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000000855 fermentation Methods 0.000 description 2
230000004151 fermentation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229960003760 florfenicol Drugs 0.000 description 2
239000001963 growth medium Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
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239000000047 product Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000004064 recycling Methods 0.000 description 2
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
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230000000707 stereoselective effect Effects 0.000 description 2
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
IVWWFWFVSWOTLP-YVZVNANGSA-N (3'as,4r,7'as)-2,2,2',2'-tetramethylspiro[1,3-dioxolane-4,6'-4,7a-dihydro-3ah-[1,3]dioxolo[4,5-c]pyran]-7'-one Chemical compound C([C@@H]1OC(O[C@@H]1C1=O)(C)C)O[C@]21COC(C)(C)O2 IVWWFWFVSWOTLP-YVZVNANGSA-N 0.000 description 1
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LMSDCGXQALIMLM-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetic acid;iron Chemical compound [Fe].OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O LMSDCGXQALIMLM-UHFFFAOYSA-N 0.000 description 1
JUCGVCVPNPBJIG-UHFFFAOYSA-N 2-amino-1-phenylpropane-1,3-diol Chemical compound OCC(N)C(O)C1=CC=CC=C1 JUCGVCVPNPBJIG-UHFFFAOYSA-N 0.000 description 1
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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 1
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ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 1
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238000010348 incorporation Methods 0.000 description 1
239000011630 iodine Chemical group 0.000 description 1
229910052740 iodine Chemical group 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
229940043265 methyl isobutyl ketone Drugs 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000746 purification Methods 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
239000012429 reaction media Substances 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010339 sodium tetraborate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000011573 trace mineral Substances 0.000 description 1
235000013619 trace mineral Nutrition 0.000 description 1
BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/06—Separation; Purification; Stabilisation; Use of additives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/26—Separation; Purification; Stabilisation; Use of additives
- C07C319/28—Separation; Purification
- 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
- C12P11/00—Preparation of sulfur-containing organic compounds
- 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
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/829—Alcaligenes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Microbiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Analytical Chemistry (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SK912-92A 1991-03-27 1992-03-26 Spôsob enantiomérneho obohacovania zmesi D- a L-treo-2-amino-3- hydroxy-3-fenylpropiónových kyselín SK282932B6 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US67610291A	1991-03-27	1991-03-27
US68930091A	1991-04-22	1991-04-22
US07/844,724 US5346828A (en)	1991-03-27	1992-03-02	Stereoisomeric enrichment of 2-amino-3-hydroxy-3-phenylpropionic acids using d-threonine aldolase

Publications (1)

Publication Number	Publication Date
SK282932B6 true SK282932B6 (sk)	2003-01-09

Family

ID=27418304

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK912-92A SK282932B6 (sk)	1991-03-27	1992-03-26	Spôsob enantiomérneho obohacovania zmesi D- a L-treo-2-amino-3- hydroxy-3-fenylpropiónových kyselín

Country Status (17)

Country	Link
US (1)	US5346828A (es)
EP (1)	EP0507153B1 (es)
JP (1)	JP3142627B2 (es)
KR (1)	KR100250513B1 (es)
AT (1)	ATE155175T1 (es)
AU (1)	AU645895B2 (es)
CA (1)	CA2064349C (es)
CZ (1)	CZ289218B6 (es)
DE (1)	DE69220701T2 (es)
DK (1)	DK0507153T3 (es)
ES (1)	ES2106101T3 (es)
GR (1)	GR3024971T3 (es)
HU (1)	HU214305B (es)
IE (1)	IE920866A1 (es)
IL (1)	IL101268A (es)
NZ (1)	NZ242040A (es)
SK (1)	SK282932B6 (es)

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TW397866B (en)	1993-07-14	2000-07-11	Bristol Myers Squibb Co	Enzymatic processes for the resolution of enantiomeric mixtures of compounds useful as intermediates in the preparation of taxanes
EP0734453A1 (en) *	1993-12-17	1996-10-02	Dsm N.V.	Phenylserine amides and the preparation of phenylserines/phenylserine amides
US7172885B2 (en) *	2004-12-10	2007-02-06	Cambrex North Brunswick, Inc.	Thermostable omega-transaminases
EP1882737B1 (en) *	2005-05-20	2011-09-14	Ajinomoto Co., Inc.	Process for production of l-serine derivative and enzyme used in the process
US7518017B2 (en)	2006-02-17	2009-04-14	Idexx Laboratories	Fenicol compounds and methods synthesizing 2-trifluoroacetamido-3-substituted propiophenone compounds
KR100758512B1 (ko)	2006-07-20	2007-09-14	엔자이텍 주식회사	효소적 방법에 의한 광학활성3-히드록시-3-페닐프로피온산과 광학활성3-아실옥시-3-페닐프로피온산의 제조 방법
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
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
CN101941927B (zh) *	2010-09-28	2012-10-03	湖北美天生物科技有限公司	氟苯尼考中间体(1r,2r)-2-氨基-1–(4-(甲砜基)苯基)-1,3-丙二醇的合成方法
CN115611785B (zh) *	2022-12-19	2023-03-14	天津工微生物科技有限公司	(2r,3s)-2-氨基-3-羟基-3-(4-(甲基磺酰基)苯基)丙酸的纯化方法

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US3733352A (en) *	1969-07-29	1973-05-15	Sumitomo Chemical Co	Preparation of d-threo-1-p-methyl-sulfonylphenyl-2-dichloro-acet-amidopropane-1,3-diol
US3871958A (en) *	1972-03-04	1975-03-18	Ajinomoto Kk	Biological method of producing serine and serinol derivatives
FR2378746A1 (fr)	1977-01-28	1978-08-25	Synthelabo	Derives d'acides a-amines
US4235892A (en) *	1979-02-05	1980-11-25	Schering Corporation, Patent Dept.	1-Aryl-2-acylamido-3-fluoro-1-propanols, methods for their use as antibacterial agents and compositions useful therefor
US4492757A (en) *	1981-12-28	1985-01-08	Denki Kagaku Kogyo Kabushiki Kaisha	Process for preparing L-threonine
US4582918A (en) *	1984-09-19	1986-04-15	Schering Corporation	Preparation of intermediates for (threo)-1-aryl-2-acylamido-3-fluoro-1-propanols
US4677214A (en) *	1984-09-19	1987-06-30	Schering Corporation	Intermediates for preparation of (threo)-1-aryl-2-acylamido-3-fluoro-1-propanols
DE3543021A1 (de) *	1985-12-05	1987-06-11	Boehringer Mannheim Gmbh	Verbesserte verfahren zur herstellung von d-threo-1-(p-methylsulfonylphenyl) -2-dichloracetamido-propandiol-1,3-(thiamphenicol) sowie verwendung geeigneter zwischenprodukte
KR920701469A (ko) *	1989-05-15	1992-08-11	스테이너 브이. 캔스태드	향균성 화합물 및 이의 중간물질의 제조방법
AU6052090A (en) *	1989-07-07	1991-02-06	Schering Corporation	Process for producing antibacterial intermediates via enzyme hydrolysis of racemic substrates

1992
- 1992-03-02 US US07/844,724 patent/US5346828A/en not_active Expired - Lifetime
- 1992-03-18 IL IL10126892A patent/IL101268A/xx not_active IP Right Cessation
- 1992-03-18 NZ NZ242040A patent/NZ242040A/xx not_active IP Right Cessation
- 1992-03-18 IE IE086692A patent/IE920866A1/en not_active IP Right Cessation
- 1992-03-19 AT AT92104752T patent/ATE155175T1/de active
- 1992-03-19 DE DE69220701T patent/DE69220701T2/de not_active Expired - Lifetime
- 1992-03-19 ES ES92104752T patent/ES2106101T3/es not_active Expired - Lifetime
- 1992-03-19 EP EP92104752A patent/EP0507153B1/en not_active Expired - Lifetime
- 1992-03-19 DK DK92104752.8T patent/DK0507153T3/da active
- 1992-03-23 JP JP04065132A patent/JP3142627B2/ja not_active Expired - Lifetime
- 1992-03-23 CA CA002064349A patent/CA2064349C/en not_active Expired - Lifetime
- 1992-03-23 AU AU13106/92A patent/AU645895B2/en not_active Expired
- 1992-03-26 CZ CS1992912A patent/CZ289218B6/cs not_active IP Right Cessation
- 1992-03-26 SK SK912-92A patent/SK282932B6/sk not_active IP Right Cessation
- 1992-03-27 HU HU9201041A patent/HU214305B/hu unknown
- 1992-03-27 KR KR1019920005107A patent/KR100250513B1/ko not_active Expired - Lifetime
1997
- 1997-10-09 GR GR970402613T patent/GR3024971T3/el unknown

Also Published As

Publication number	Publication date
HU9201041D0 (en)	1992-06-29
AU645895B2 (en)	1994-01-27
ATE155175T1 (de)	1997-07-15
HU214305B (hu)	1998-03-02
CZ289218B6 (cs)	2001-12-12
KR920018012A (ko)	1992-10-21
JP3142627B2 (ja)	2001-03-07
JPH06125790A (ja)	1994-05-10
EP0507153A3 (en)	1993-12-15
CA2064349A1 (en)	1992-09-28
KR100250513B1 (ko)	2000-04-01
US5346828A (en)	1994-09-13
AU1310692A (en)	1992-10-01
CS91292A3 (en)	1992-12-16
DK0507153T3 (da)	1997-12-22
ES2106101T3 (es)	1997-11-01
CA2064349C (en)	2003-11-25
IL101268A (en)	1997-02-18
EP0507153B1 (en)	1997-07-09
GR3024971T3 (en)	1998-01-30
DE69220701T2 (de)	1997-11-06
IL101268A0 (en)	1992-11-15
HUT62261A (en)	1993-04-28
DE69220701D1 (de)	1997-08-14
NZ242040A (en)	1993-06-25
IE920866A1 (en)	1992-10-07
EP0507153A2 (en)	1992-10-07

Legal Events

Date	Code	Title	Description
2012-05-03	MK4A	Patent expired	Expiry date: 20120326

Publication	Publication Date	Title
SK282932B6 (sk)	2003-01-09	Spôsob enantiomérneho obohacovania zmesi D- a L-treo-2-amino-3- hydroxy-3-fenylpropiónových kyselín
JP2009022270A (ja)	2009-02-05	Ｎ−アシルアゼチジン−２−カルボン酸の生物学的分割
RS20050092A (sr)	2007-09-21	Postupak za separaciju intermedijara koji može da se upotrebi za preparaciju escitaloprama
WO1997020817A1 (fr)	1997-06-12	Procede de separation de carbinols
US4980291A (en)	1990-12-25	Process for the enzymatic separation of the optical isomers of racemic α-alkyl-substituted primary alcohols
JP2007519655A (ja)	2007-07-19	鏡像異性的に純粋なアミノアルコールの調製方法
US5302528A (en)	1994-04-12	Process for the enzymatic separation of the optical isomers of alpha-substituted carboxylic acids using esterase from Brevibacterium imperiale
JPS63245686A (ja)	1988-10-12	ラセミオキサゾリジノン系誘導体の光学異性体の酵素分離方法
US5811294A (en)	1998-09-22	Production of optically active 1,2-dihydroxyindance derivatives by asymetric assimilation
JPH01501360A (ja)	1989-05-18	立体特異的酵素的アシレート加水分解による７α―アシルオキシ―６β―ヒドロキシ―メチル―２―オキサビシクロ〔３．３．０〕オクタン―３―オンのラセミ化合物分割方法
JP5216762B2 (ja)	2013-06-19	（ｓ）−１−メチル−フェニルピペラジンの立体選択的合成
RU2112805C1 (ru)	1998-06-10	Способ энантиомерного обогащения смеси d- и l-трео-2-амино-3-гидрокси-3-фенилпропионовых кислот, или их производных, или их солей
Schaffrath et al.	2001	Biosynthesis of fluoroacetate and 4-fluorothreonine in Streptomyces cattleya. Incorporation of oxygen-18 from [2-2 H, 2-18 O]-glycerol and the role of serine metabolites in fluoroacetaldehyde biosynthesis
CA2054773C (en)	1997-04-01	Protected hydroxy method for alcohol-ester separation
EP2196458A1 (en)	2010-06-16	Process for obtaining enantiomerically enriched pyrazole derivatives
US5217886A (en)	1993-06-08	Method for the production of (-)-4-difluoromethyl-ornithine
JP3836873B2 (ja)	2006-10-25	置換２−メチル−プロピオン酸の酵素的分割
JP3636733B2 (ja)	2005-04-06	光学活性２−ヒドロキシ−３−ニトロプロピオン酸およびその対掌体エステルの製造法
JPH1014590A (ja)	1998-01-20	光学活性２−置換−３−フェニルプロピオン酸及びそのエステルの製造方法
JP3010382B2 (ja)	2000-02-21	（ｒ）−２−プロポキシベンゼン誘導体の製造法
JP4270910B2 (ja)	2009-06-03	光学活性２−ヒドロキシ−２−トリフルオロ酢酸類の製造方法
JP3970898B2 (ja)	2007-09-05	光学活性α−メチルアルカンジカルボン酸−ω−モノエステル及びその対掌体ジエステルを製造する方法
JPH02190195A (ja)	1990-07-26	光学活性プロピオン酸エステル類化合物の製法
WO1993002207A1 (en)	1993-02-04	Stereoselective synthesis of alcohols
JPH0965891A (ja)	1997-03-11	光学活性α−メチルアルカン酸誘導体の製造方法