DD272870A5 - Verfahren zur racematspaltung von aktiven phosphorhaltigen funktionellen essigsaeurederivate - Google Patents

Verfahren zur racematspaltung von aktiven phosphorhaltigen funktionellen essigsaeurederivate Download PDF

Info

Publication number: DD272870A5
Authority: DD; German Democratic Republic
Prior art keywords: aqueous; alkyl; reaction; compound; racemating
Prior art date: 1987-08-15

Application number

DD88318907A

Other languages

German (de)

English (en)

Inventor

Dieter Wullbrandt

Reinhold Keller

Merten Schlingmann

Wolfgang Holla

Manfred Schneider

Original Assignee

��@��k��

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.)

1987-08-15

Filing date

1988-08-12

Publication date

1989-10-25

1988-08-12 Application filed by ��@��k�� filed Critical ��@��k��

1989-10-25 Publication of DD272870A5 publication Critical patent/DD272870A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 19
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 title 1
235000021419 vinegar Nutrition 0.000 title 1
239000000052 vinegar Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 15
108090000371 Esterases Proteins 0.000 claims abstract description 12
108090001060 Lipase Proteins 0.000 claims abstract description 9
239000004367 Lipase Substances 0.000 claims abstract description 9
102000004882 Lipase Human genes 0.000 claims abstract description 9
235000019421 lipase Nutrition 0.000 claims abstract description 9
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 7
239000011574 phosphorus Substances 0.000 claims abstract description 7
229910052698 phosphorus Inorganic materials 0.000 claims abstract description 7
150000001242 acetic acid derivatives Chemical class 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
238000006243 chemical reaction Methods 0.000 claims description 16
210000004185 liver Anatomy 0.000 claims description 7
-1 compound (±) dimethyl-phosphinoyl-hydroxyacetic acid ester Chemical class 0.000 claims description 6
239000012429 reaction media Substances 0.000 claims description 2
241000222120 Candida <Saccharomycetales> Species 0.000 claims 1
241000196324 Embryophyta Species 0.000 abstract description 5
230000002363 herbicidal effect Effects 0.000 abstract description 5
239000003795 chemical substances by application Substances 0.000 abstract description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
102000004190 Enzymes Human genes 0.000 description 7
108090000790 Enzymes Proteins 0.000 description 7
230000000694 effects Effects 0.000 description 7
150000003839 salts Chemical class 0.000 description 5
239000000758 substrate Substances 0.000 description 5
UTDPHALOLFEIHB-UHFFFAOYSA-N 2-dimethylphosphoryl-2-hydroxyacetic acid Chemical compound CP(C)(=O)C(O)C(O)=O UTDPHALOLFEIHB-UHFFFAOYSA-N 0.000 description 4
108090000604 Hydrolases Proteins 0.000 description 4
102000004157 Hydrolases Human genes 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
230000002255 enzymatic effect Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000012064 sodium phosphate buffer Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241000179532 [Candida] cylindracea Species 0.000 description 2
239000013543 active substance Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000872 buffer Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
229960004275 glycolic acid Drugs 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
108091005804 Peptidases Proteins 0.000 description 1
102000035195 Peptidases Human genes 0.000 description 1
239000004365 Protease Substances 0.000 description 1
241000235403 Rhizomucor miehei Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229930182558 Sterol Natural products 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002152 aqueous-organic solution Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
235000015277 pork Nutrition 0.000 description 1
239000008057 potassium phosphate buffer Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
ZRJSSGYQNKQTLX-UHFFFAOYSA-M sodium 2-dimethylphosphoryl-2-hydroxyacetate Chemical compound [Na+].CP(C)(=O)C(O)C([O-])=O ZRJSSGYQNKQTLX-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
108010079522 solysime Proteins 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
150000003432 sterols Chemical class 0.000 description 1
235000003702 sterols Nutrition 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/005—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of carboxylic acid groups in the enantiomers or the inverse reaction
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3211—Esters of acyclic saturated acids which can have further substituents on alkyl
- 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
- C12P9/00—Preparation of organic compounds containing a metal or atom other than H, N, C, O, S or halogen

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)
General Health & Medical Sciences (AREA)
Biochemistry (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Genetics & Genomics (AREA)
General Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Microbiology (AREA)
Biotechnology (AREA)
Molecular Biology (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Analytical Chemistry (AREA)
Environmental Sciences (AREA)
Plant Pathology (AREA)
Dentistry (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD88318907A 1987-08-15 1988-08-12 Verfahren zur racematspaltung von aktiven phosphorhaltigen funktionellen essigsaeurederivate DD272870A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19873727243 DE3727243A1 (de)	1987-08-15	1987-08-15	Verfahren zur enzymatischen herstellung optisch aktiver phosphorhaltiger funktioneller essigsaeurederivate

Publications (1)

Publication Number	Publication Date
DD272870A5 true DD272870A5 (de)	1989-10-25

Family

ID=6333834

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88318907A DD272870A5 (de)	1987-08-15	1988-08-12	Verfahren zur racematspaltung von aktiven phosphorhaltigen funktionellen essigsaeurederivate

Country Status (12)

Country	Link
US (1)	US5010012A (fr)
EP (1)	EP0303947A3 (fr)
JP (1)	JPH0191794A (fr)
KR (1)	KR890003955A (fr)
AU (1)	AU617344B2 (fr)
DD (1)	DD272870A5 (fr)
DE (1)	DE3727243A1 (fr)
DK (1)	DK453988A (fr)
HU (1)	HU203791B (fr)
IL (1)	IL87429A0 (fr)
NZ (1)	NZ225806A (fr)
ZA (1)	ZA885968B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3903446A1 (de) *	1989-02-06	1990-10-18	Hoechst Ag	Verfahren zur enzymatischen trennung von 2-amino-4-methylphosphinobuttersaeurederivaten
JPH02273196A (ja) *	1989-03-08	1990-11-07	Wisconsin Alumni Res Found	ラセミ化合物の生体触媒分割のエナンチオ選択性の改良法
US6277879B1 (en)	1994-08-03	2001-08-21	Sarawak Medichem Pharmaceuticals, Inc.	Calanolide analogues and methods of their use
CA2303112C (fr)	1998-10-19	2003-03-18	Kawasaki Jukogyo Kabushiki Kaisha	Soupape de regulation de debit de materiau granulaire et en poudre
US6369241B1 (en)	1999-04-26	2002-04-09	Sarawak Medichem Pharmaceuticals, Inc.	Methods for preparing antiviral calanolide compounds

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3238958A1 (de) *	1982-09-10	1984-03-15	Hoechst Ag, 6230 Frankfurt	Phosphorhaltige funktionelle essigsaeurederivate, verfahren zu ihrer herstellung und sie enthaltende heribizide und wachstumsregulierende mittel
EP0130752B1 (fr) *	1983-07-04	1991-02-27	Mitsubishi Rayon Co., Ltd.	Procédé de préparation d'acides carboxyliques optiquement actifs et de leurs esters antipodes
US4601987A (en) *	1985-02-27	1986-07-22	Massachusetts Institute Of Technology	Enzymatic production of optical isomers of 2-halopropionic acids
US4668628A (en) *	1985-04-01	1987-05-26	Stauffer Chemical Company	Resolution of racemic mixtures of aliphatic acid esters
DE3614787A1 (de) *	1985-10-10	1987-04-16	Hoechst Ag	Herbizide mittel

1987
- 1987-08-15 DE DE19873727243 patent/DE3727243A1/de not_active Withdrawn
1988
- 1988-08-10 EP EP88112952A patent/EP0303947A3/fr not_active Withdrawn
- 1988-08-12 DK DK453988A patent/DK453988A/da not_active Application Discontinuation
- 1988-08-12 ZA ZA885968A patent/ZA885968B/xx unknown
- 1988-08-12 AU AU20653/88A patent/AU617344B2/en not_active Expired - Fee Related
- 1988-08-12 US US07/231,290 patent/US5010012A/en not_active Expired - Fee Related
- 1988-08-12 NZ NZ225806A patent/NZ225806A/en unknown
- 1988-08-12 JP JP63200281A patent/JPH0191794A/ja active Pending
- 1988-08-12 IL IL87429A patent/IL87429A0/xx unknown
- 1988-08-12 DD DD88318907A patent/DD272870A5/de not_active IP Right Cessation
- 1988-08-13 KR KR1019880010336A patent/KR890003955A/ko not_active Withdrawn
- 1988-08-15 HU HU884357A patent/HU203791B/hu unknown

Also Published As

Publication number	Publication date
EP0303947A2 (fr)	1989-02-22
ZA885968B (en)	1989-04-26
AU617344B2 (en)	1991-11-28
JPH0191794A (ja)	1989-04-11
HU203791B (en)	1991-09-30
AU2065388A (en)	1989-02-16
IL87429A0 (en)	1989-01-31
DK453988D0 (da)	1988-08-12
US5010012A (en)	1991-04-23
KR890003955A (ko)	1989-04-19
HUT49648A (en)	1989-10-30
NZ225806A (en)	1991-04-26
DE3727243A1 (de)	1989-02-23
DK453988A (da)	1989-02-16
EP0303947A3 (fr)	1990-07-04

Legal Events

Date	Code	Title	Description
1994-06-23	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE3783327T2 (de)	1993-04-22	Verfahren zur herstellung von optisch aktiven verbindungen.
DE3424440C2 (fr)	1990-04-12
DE3872924T2 (de)	1993-01-21	Verfahren zur herstellung von optisch aktiven verbindungen.
DE69914458T2 (de)	2004-10-28	Verfahren zur enzymatischen auflösung von laktamen
DE3876039T2 (de)	1993-04-22	Verfahren zur herstellung von optisch aktiven verbindungen mit pyridin-kernen.
DE3048612A1 (de)	1982-07-01	"verfahren zur enzymatischen herstellung von l-2-amino-4-methylphosphinobuttersaeure"
DE3886445T2 (de)	1994-05-19	Optisch-aktive Verbindungen und Verfahren zu deren Herstellung.
EP0382113B1 (fr)	1994-09-21	Procédé de séparation enzymatique de dérivés de l'acide amino-2-méthyl-4-phosphinobutyrique
DD272870A5 (de)	1989-10-25	Verfahren zur racematspaltung von aktiven phosphorhaltigen funktionellen essigsaeurederivate
DE3418374A1 (de)	1985-11-21	Verfahren zur herstellung von cyclopropancarbonsaeuren
DE3781906T2 (de)	1993-02-25	Verfahren zum herstellen eines optisch aktiven alkohols mittels eines biochemischen verfahrens.
DE3532026A1 (de)	1987-03-19	Verfahren zur herstellung optisch aktiver (alpha)-phenoxypropionsaeure und deren derivate
EP0402771A1 (fr)	1990-12-19	Procédé de dédoublement enzymatique d'esters vinyliques d'acides 2-aryl propioniques
DE19955283A1 (de)	2001-05-23	Verfahren zur enantioselektiven Gewinnung von Aminosäuren und Aminosäurederivaten unter Verwendung von Racemisierungskatalysatoren
AT398579B (de)	1994-12-27	Enzymatisches verfahren zur trennung racemischer gemische von delta-valerolactonen
DE69232661T2 (de)	2003-02-20	Enzymatischer prozess zur herstellung von cefonicid
DE69904658T2 (de)	2003-11-06	Gegen Ralstonia Solanacearum aktive bakterizide Zusammensetzungen
EP0910660B1 (fr)	2003-01-22	Procede de production d'amines optiquement actives
DD295358A5 (de)	1991-10-31	Verfahren zur racemattrennung von 4-aryl-2-oxo-pyrrolidin-3-carbonsaeure-estern
EP0511526A1 (fr)	1992-11-04	Procédé de hydrolyse enzymatique d'un dérivé d'acide carboxylique
EP0407909B1 (fr)	1994-11-02	Procédé de préparation d'esters alcoyliques inférieurs de l'acide R-(+)-3-oxocycloalkane carboxylique
EP0877815A1 (fr)	1998-11-18	Procede de preparation d'amines optiquement actives
DE4009709A1 (de)	1990-10-04	Optisch aktive verbindung und verfahren zu ihrer herstellung
EP0528256B1 (fr)	1996-09-25	D-2,4-dihydroxy-3,3-diméthylbutyronitrile, sa production et son utilisation et procédé de production de D-pantolactone, D-2,4-dihydroxy-3,3-diméthylbutyramide et D-acid pantothénique
DE60010013T2 (de)	2005-03-31	Verfahren zur Herstellung von optisch aktivem 1,2,4-Butantriol und optisch aktivem 3-Hydroxy-gamma-butyrolacton mittels Mikroorganismen