AU599985B2 - New process for the production of L-2-amino-4- (hydroxymethyl-phosphinyl)-butyric acid - Google Patents
New process for the production of L-2-amino-4- (hydroxymethyl-phosphinyl)-butyric acid Download PDFInfo
- Publication number
- AU599985B2 AU599985B2 AU73750/87A AU7375087A AU599985B2 AU 599985 B2 AU599985 B2 AU 599985B2 AU 73750/87 A AU73750/87 A AU 73750/87A AU 7375087 A AU7375087 A AU 7375087A AU 599985 B2 AU599985 B2 AU 599985B2
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- Australia
- Prior art keywords
- amino
- atcc
- transaminase
- ampb
- butyric acid
- Prior art date
- Legal status (The legal status 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 status listed.)
- Ceased
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- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000001851 biosynthetic effect Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 229940049906 glutamate Drugs 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 229960002743 glutamine Drugs 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960002885 histidine Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229960003136 leucine Drugs 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 229960000274 lysozyme Drugs 0.000 description 1
- 239000004325 lysozyme Substances 0.000 description 1
- 235000010335 lysozyme Nutrition 0.000 description 1
- 235000020429 malt syrup Nutrition 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229960004452 methionine Drugs 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- KHPXUQMNIQBQEV-UHFFFAOYSA-N oxaloacetic acid Chemical compound OC(=O)CC(=O)C(O)=O KHPXUQMNIQBQEV-UHFFFAOYSA-N 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000002731 protein assay Methods 0.000 description 1
- 235000019624 protein content Nutrition 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229960004799 tryptophan Drugs 0.000 description 1
- 229960004441 tyrosine Drugs 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000005253 yeast cell Anatomy 0.000 description 1
- 239000012138 yeast extract Substances 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
Landscapes
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61-131743 | 1986-06-09 | ||
| JP13174386 | 1986-06-09 | ||
| JP1251387 | 1987-01-23 | ||
| JP62-12513 | 1987-01-23 | ||
| JP7447687 | 1987-03-30 | ||
| JP62-74476 | 1987-03-30 | ||
| JP10115287 | 1987-04-25 | ||
| JP62-101152 | 1987-04-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU7375087A AU7375087A (en) | 1987-12-10 |
| AU599985B2 true AU599985B2 (en) | 1990-08-02 |
Family
ID=27455820
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU73750/87A Ceased AU599985B2 (en) | 1986-06-09 | 1987-06-02 | New process for the production of L-2-amino-4- (hydroxymethyl-phosphinyl)-butyric acid |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0249188B1 (enExample) |
| JP (1) | JP2589693B2 (enExample) |
| KR (1) | KR940005654B1 (enExample) |
| CN (1) | CN87105130A (enExample) |
| AT (1) | ATE111530T1 (enExample) |
| AU (1) | AU599985B2 (enExample) |
| DE (1) | DE3750523T2 (enExample) |
| DK (1) | DK289687A (enExample) |
| ES (1) | ES2059324T3 (enExample) |
| HU (1) | HU200342B (enExample) |
| IL (1) | IL82786A0 (enExample) |
| IN (1) | IN165699B (enExample) |
| NZ (1) | NZ220576A (enExample) |
| SU (1) | SU1731067A3 (enExample) |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4826766A (en) * | 1985-09-23 | 1989-05-02 | Genetics Institute, Inc. | Production of amino acids using coupled aminotransferases |
| ES2144999T3 (es) * | 1986-06-04 | 2000-07-01 | Hoechst Schering Agrevo Gmbh | Procedimiento para la preparacion de l-leucina terciaria mediante transaminacion. |
| 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 |
| JPH0693839B2 (ja) * | 1988-10-27 | 1994-11-24 | 明治製菓株式会社 | Ｌ−２−アミノ−４−（ヒドロキシメチルホスフィニル）酪酸の製造方法 |
| DE3842025A1 (de) * | 1988-12-14 | 1990-07-05 | Hoechst Ag | Verfahren zur herstellung von l-phosphinothricin |
| DE3920570A1 (de) * | 1989-06-23 | 1991-01-03 | Hoechst Ag | Verfahren zur isolierung von l-2-amino-4-methylphosphinobuttersaeure-ammoniumsalz aus einer enzymatischen transaminierungsloesung |
| DE4030578A1 (de) | 1990-09-27 | 1992-04-16 | Hoechst Ag | Verfahren zur herstellung von l-phosphinothricin durch eine gekoppelte enzymatische reaktion |
| TW353663B (en) * | 1991-04-06 | 1999-03-01 | Hoechst Ag | Process for the preparation of phosphorus-containing L-amino acids, their derivatives and intermediates for this process |
| IL101539A (en) | 1991-04-16 | 1998-09-24 | Monsanto Europe Sa | Non-hygroscopic mono-ammonium salts of n-phosphonomethyl glycine derivatives their preparation and pesticidal compositons containing them |
| HU212802B (en) | 1991-07-19 | 1996-11-28 | Monsanto Europe Sa | Phytoactive sack-like composition containing glyphosate-izopropylamine salt |
| JPH06245780A (ja) * | 1993-02-25 | 1994-09-06 | Meiji Seika Kaisha Ltd | Ｌ−２−アミノ−４−（ヒドロキシメチルホスフィニル）−酪酸の製造法 |
| DE19919848A1 (de) * | 1999-04-30 | 2000-11-02 | Aventis Cropscience Gmbh | Verfahren zur Herstellung von L-Phosphinothricin durch enzymatische Transaminierung mit Aspartat |
| US6910691B2 (en) * | 2003-03-04 | 2005-06-28 | Sywan-Min Shih | Cubic puzzle |
| CN101395271B (zh) * | 2006-03-02 | 2013-02-27 | 明治制果株式会社 | 天冬氨酸转氨酶基因和l-膦丝菌素的制备方法 |
| 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 |
| EP2762484A4 (en) | 2011-09-30 | 2015-05-06 | Meiji Seika Pharma Co Ltd | PROCESS FOR PREPARING A GLUFOSINATE P-FREE ACIDITY |
| WO2016180755A1 (en) | 2015-05-11 | 2016-11-17 | Bayer Cropscience Aktiengesellschaft | Herbicide combinations comprising l-glufosinate and indaziflam |
| CN105567780A (zh) * | 2016-01-14 | 2016-05-11 | 重庆惠健生物科技有限公司 | 一种l-草铵膦的酶-化学催化去消旋化制备方法 |
| CN105603015B (zh) * | 2016-01-22 | 2018-12-11 | 浙江大学 | 一种l-草铵膦的生产方法 |
| CN116121315A (zh) | 2016-03-02 | 2023-05-16 | 巴斯夫欧洲公司 | 制造l-草胺膦的方法 |
| WO2018108794A1 (de) | 2016-12-15 | 2018-06-21 | Bayer Cropscience Aktiengesellschaft | Verfahren zur herstellung von d-glufosinat oder dessen salzen unter verwendung von ephedrin |
| WO2018108797A1 (de) | 2016-12-15 | 2018-06-21 | Bayer Cropscience Aktiengesellschaft | Verfahren zur herstellung von l-glufosinat oder dessen salzen unter verwendung von ephedrin |
| CA3070104C (en) | 2017-07-18 | 2023-08-08 | Agrimetis, Llc | Methods for the purification of l-glufosinate and crystalline l-glufosinate ammonium forms |
| CA3069815A1 (en) | 2017-07-27 | 2019-01-31 | Basf Se | Use of herbicidal compositions based on l-glufosinate in tolerant field crops |
| CN108484665B (zh) * | 2018-04-16 | 2020-06-23 | 浙江工业大学 | 一种从酶转化液中分离提取l-草铵膦的方法 |
| EP3847269A1 (en) | 2018-09-05 | 2021-07-14 | Basf Se | Methods for improving yields of l-glufosinate |
| BR112022014435A2 (pt) | 2020-01-23 | 2022-09-13 | Basf Se | Composição herbicida líquida e métodos para aumentar a atividade herbicida de composições herbicidas líquidas e para tratar o material de propagação de plantas |
| US20230088774A1 (en) | 2020-01-31 | 2023-03-23 | Basf Se | Herbicide Combinations Comprising Glufosinate and Oxadiazon |
| BR112022015061A2 (pt) | 2020-01-31 | 2022-09-20 | Basf Se | Combinação de herbicidas, composição, métodos para produzir uma combinação de herbicidas, para controlar o crescimento indesejado das plantas, para tratar ou proteger culturas e uso de uma combinação de herbicidas |
| US20230060640A1 (en) | 2020-01-31 | 2023-03-02 | Basf Se | Herbicide combinations comprising glufosinate and pyraflufen-ethyl |
| WO2021151740A1 (en) | 2020-01-31 | 2021-08-05 | Basf Se | Herbicide combinations comprising glufosinate and sulfentrazone |
| BR112022014950A2 (pt) | 2020-01-31 | 2022-09-20 | Basf Se | Combinação de herbicidas, composição, métodos de produção de combinações de herbicidas, de controle do crescimento vegetal indesejado e de tratamento ou proteção de plantas e uso da combinação de herbicidas |
| US20220378042A1 (en) | 2020-01-31 | 2022-12-01 | Basf Se | Herbicide combinations comprising glufosinate and oxyfluorfen |
| US20230067406A1 (en) | 2020-01-31 | 2023-03-02 | Basf Se | Herbicide Combinations Comprising Glufosinate and Flumioxazin |
| WO2021151734A1 (en) | 2020-01-31 | 2021-08-05 | Basf Se | Herbicide combinations comprising glufosinate and flumiclorac-pentyl |
| BR112022014824A2 (pt) | 2020-01-31 | 2022-12-13 | Basf Se | Combinação de herbicidas, composição, métodos de produção de combinações herbicidas, de tratamento ou proteção de plantas produtoras em fileiras e de tratamento ou proteção de plantas especializadas e uso da composição herbicida |
| BR112022014960A2 (pt) | 2020-01-31 | 2022-09-20 | Basf Se | Combinação de herbicidas, composição, métodos de produção de uma combinação de herbicidas, para controlar o crescimento de plantas indesejadas, para tratar ou proteger culturas em linha e culturas de especialidades e uso |
| BR112022014955A2 (pt) | 2020-01-31 | 2022-09-20 | Basf Se | Combinação herbicida, composição, métodos para produzir uma combinação herbicida, para controlar o crescimento indesejado das plantas e/ou controlar plantas nocivas, para tratar ou proteger culturas em linha e para tratar ou proteger culturas especiais e uso de combinação herbicida |
| US20230068414A1 (en) | 2020-01-31 | 2023-03-02 | Basf Se | Herbicide combinations comprising glufosinate and trifludimoxazin |
| US20230086500A1 (en) | 2020-01-31 | 2023-03-23 | Basf Se | Herbicide Combinations Comprising Glufosinate and S-3100 |
| BR112022014971A2 (pt) | 2020-01-31 | 2022-09-20 | Basf Se | Combinação herbicida, composição, métodos para produzir uma combinação herbicida, para controlar o crescimento indesejado das plantas e para tratar ou proteger culturas e uso de combinações herbicidas |
| EP4000400A1 (en) | 2020-11-17 | 2022-05-25 | Basf Se | Herbicide combination comprising glufosinate, saflufenacil and trifludimoxazin |
| AU2021360993A1 (en) | 2020-10-12 | 2023-05-18 | Basf Se | Herbicide combination comprising glufosinate, saflufenacil and trifludimoxazin |
| CN116507203A (zh) | 2020-10-27 | 2023-07-28 | 巴斯夫欧洲公司 | 农药微乳剂组合物 |
| US20240138402A1 (en) | 2021-02-05 | 2024-05-02 | Basf Se | Liquid herbicidal compositions |
| JP2024513190A (ja) | 2021-04-01 | 2024-03-22 | ビーエーエスエフ ソシエタス・ヨーロピア | Ｌ－グルホシネートを調製するための方法 |
| US20240248442A1 (en) | 2021-05-21 | 2024-07-25 | Basf Se | Computer-implemented method for applying a glutamine synthetase inhibitor on an agricultural field |
| EP4432830A1 (en) | 2021-11-15 | 2024-09-25 | Basf Se | Method for increasing the efficacy of a herbicide |
| AU2022405733A1 (en) | 2021-12-10 | 2024-06-20 | Basf Se | Synthesis of glufosinate using a hydantoinase-based process |
| MX2024007021A (es) | 2021-12-10 | 2024-06-19 | Basf Se | Descarbamoilacion enzimatica de derivados de glufosinato. |
| KR20250059530A (ko) | 2022-09-14 | 2025-05-02 | 바스프 에스이 | 제초제의 효능을 개선하기 위한 알킬에테르 술페이트의 용도 |
| EP4338592A1 (en) | 2022-09-15 | 2024-03-20 | Basf Se | Use of compound for improving the efficacy of herbicides |
| WO2024175643A1 (en) | 2023-02-23 | 2024-08-29 | Basf Se | A process for preparing l-glufosinate from cyanhydrine or cyanhydrine derivatives |
| AR132932A1 (es) | 2023-06-13 | 2025-08-13 | Basf Se | Síntesis de glufosinato mediante un proceso basado en amidasa |
| WO2025061719A1 (en) | 2023-09-21 | 2025-03-27 | Specialty Operations France | Emulsion in water concentrate comprising glufosinate, vlcfa inhibitor and specific surfactants |
| WO2025061721A1 (en) | 2023-09-21 | 2025-03-27 | Specialty Operations France | Herbicidal compositions comprising specific surfactants |
| WO2025219238A1 (en) | 2024-04-15 | 2025-10-23 | Basf Se | Process for producing l-glufosinate from a diol or diol derivative |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4466913A (en) * | 1981-06-30 | 1984-08-21 | Maiji Seika Kaisha Ltd. | Phosphorus-containing compounds and process for producing the same |
| SE8502315L (sv) * | 1984-07-05 | 1986-01-06 | Grace W R & Co | Forbettrat transamineringsforfarande for framstellning av aminosyror |
| ES2144999T3 (es) * | 1986-06-04 | 2000-07-01 | Hoechst Schering Agrevo Gmbh | Procedimiento para la preparacion de l-leucina terciaria mediante transaminacion. |
-
1987
- 1987-06-02 AU AU73750/87A patent/AU599985B2/en not_active Ceased
- 1987-06-03 IN IN438/CAL/87A patent/IN165699B/en unknown
- 1987-06-04 DK DK289687A patent/DK289687A/da not_active Application Discontinuation
- 1987-06-05 IL IL82786A patent/IL82786A0/xx unknown
- 1987-06-05 NZ NZ220576A patent/NZ220576A/xx unknown
- 1987-06-05 JP JP62139933A patent/JP2589693B2/ja not_active Expired - Lifetime
- 1987-06-08 HU HU872606A patent/HU200342B/hu not_active IP Right Cessation
- 1987-06-08 SU SU874202766A patent/SU1731067A3/ru active
- 1987-06-08 CN CN198787105130A patent/CN87105130A/zh active Pending
- 1987-06-09 AT AT87108292T patent/ATE111530T1/de not_active IP Right Cessation
- 1987-06-09 DE DE3750523T patent/DE3750523T2/de not_active Expired - Lifetime
- 1987-06-09 KR KR1019870005835A patent/KR940005654B1/ko not_active Expired - Lifetime
- 1987-06-09 ES ES87108292T patent/ES2059324T3/es not_active Expired - Lifetime
- 1987-06-09 EP EP87108292A patent/EP0249188B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DK289687A (da) | 1987-12-10 |
| DE3750523T2 (de) | 1995-02-02 |
| CN87105130A (zh) | 1988-06-15 |
| JPS6427485A (en) | 1989-01-30 |
| HU200342B (en) | 1990-05-28 |
| DK289687D0 (da) | 1987-06-04 |
| JP2589693B2 (ja) | 1997-03-12 |
| EP0249188A3 (en) | 1989-01-25 |
| KR940005654B1 (ko) | 1994-06-22 |
| SU1731067A3 (ru) | 1992-04-30 |
| HUT46698A (en) | 1988-11-28 |
| IN165699B (enExample) | 1989-12-16 |
| ES2059324T3 (es) | 1994-11-16 |
| DE3750523D1 (de) | 1994-10-20 |
| EP0249188A2 (en) | 1987-12-16 |
| ATE111530T1 (de) | 1994-09-15 |
| IL82786A0 (en) | 1987-12-20 |
| KR880000593A (ko) | 1988-03-28 |
| EP0249188B1 (en) | 1994-09-14 |
| NZ220576A (en) | 1990-05-28 |
| AU7375087A (en) | 1987-12-10 |
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