JP4346692B2 - 微生物バイオマスからのカロテノイド結晶の単離 - Google Patents
微生物バイオマスからのカロテノイド結晶の単離 Download PDFInfo
- Publication number
- JP4346692B2 JP4346692B2 JP54774698A JP54774698A JP4346692B2 JP 4346692 B2 JP4346692 B2 JP 4346692B2 JP 54774698 A JP54774698 A JP 54774698A JP 54774698 A JP54774698 A JP 54774698A JP 4346692 B2 JP4346692 B2 JP 4346692B2
- Authority
- JP
- Japan
- Prior art keywords
- crystals
- solvent
- water
- carotene
- carotenoid
- 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.)
- Expired - Lifetime
Links
- 239000013078 crystal Substances 0.000 title claims abstract description 47
- 239000002028 Biomass Substances 0.000 title claims abstract description 21
- 230000000813 microbial effect Effects 0.000 title claims abstract description 18
- 235000021466 carotenoid Nutrition 0.000 title abstract description 38
- 150000001747 carotenoids Chemical class 0.000 title abstract description 32
- 238000002955 isolation Methods 0.000 title abstract description 3
- 239000002904 solvent Substances 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 36
- 210000004027 cell Anatomy 0.000 claims abstract description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000005406 washing Methods 0.000 claims abstract description 13
- 210000002421 cell wall Anatomy 0.000 claims abstract description 6
- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 claims description 27
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 claims description 27
- 235000013734 beta-carotene Nutrition 0.000 claims description 26
- 239000011648 beta-carotene Substances 0.000 claims description 26
- 229960002747 betacarotene Drugs 0.000 claims description 26
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- 238000005119 centrifugation Methods 0.000 claims description 14
- 239000003921 oil Substances 0.000 claims description 13
- 235000019198 oils Nutrition 0.000 claims description 13
- 239000000725 suspension Substances 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 6
- 230000006378 damage Effects 0.000 claims description 4
- 238000010908 decantation Methods 0.000 claims description 4
- 238000011084 recovery Methods 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 4
- 239000008158 vegetable oil Substances 0.000 claims description 4
- 230000005587 bubbling Effects 0.000 claims description 2
- 150000002632 lipids Chemical class 0.000 abstract description 12
- -1 carotenoid compound Chemical class 0.000 abstract description 8
- 230000001413 cellular effect Effects 0.000 abstract description 2
- 238000000605 extraction Methods 0.000 abstract description 2
- 244000005700 microbiome Species 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- 238000000855 fermentation Methods 0.000 description 4
- 230000004151 fermentation Effects 0.000 description 4
- 238000000638 solvent extraction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 241000235553 Blakeslea trispora Species 0.000 description 3
- 241000195493 Cryptophyta Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- OAIJSZIZWZSQBC-GYZMGTAESA-N lycopene Chemical compound CC(C)=CCC\C(C)=C\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C=C(/C)CCC=C(C)C OAIJSZIZWZSQBC-GYZMGTAESA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 235000012424 soybean oil Nutrition 0.000 description 3
- 239000003549 soybean oil Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- YVLPJIGOMTXXLP-UHFFFAOYSA-N 15-cis-phytoene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CC=CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C YVLPJIGOMTXXLP-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000195634 Dunaliella Species 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000005188 flotation Methods 0.000 description 2
- OENHQHLEOONYIE-MZMZTKINSA-N 1,3,3-trimethyl-2-[(1e,3e,5e,7z,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohexene Chemical compound CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-MZMZTKINSA-N 0.000 description 1
- YVLPJIGOMTXXLP-UUKUAVTLSA-N 15,15'-cis-Phytoene Natural products C(=C\C=C/C=C(\CC/C=C(\CC/C=C(\CC/C=C(\C)/C)/C)/C)/C)(\CC/C=C(\CC/C=C(\CC/C=C(\C)/C)/C)/C)/C YVLPJIGOMTXXLP-UUKUAVTLSA-N 0.000 description 1
- YVLPJIGOMTXXLP-BAHRDPFUSA-N 15Z-phytoene Natural products CC(=CCCC(=CCCC(=CCCC(=CC=C/C=C(C)/CCC=C(/C)CCC=C(/C)CCC=C(C)C)C)C)C)C YVLPJIGOMTXXLP-BAHRDPFUSA-N 0.000 description 1
- 241000235548 Blakeslea Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000235388 Mucorales Species 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 241001542817 Phaffia Species 0.000 description 1
- 241000081271 Phaffia rhodozyma Species 0.000 description 1
- 241000235400 Phycomyces Species 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000001409 beta-carotene group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 235000011765 phytoene Nutrition 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
-
- 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
- C12P23/00—Preparation of compounds containing a cyclohexene ring having an unsaturated side chain containing at least ten carbon atoms bound by conjugated double bonds, e.g. carotenes
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97201306 | 1997-05-02 | ||
| EP97201306.4 | 1997-05-02 | ||
| PCT/EP1998/002782 WO1998050574A1 (en) | 1997-05-02 | 1998-04-29 | Isolation of carotenoid crystals from microbial biomass |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001523966A JP2001523966A (ja) | 2001-11-27 |
| JP2001523966A5 JP2001523966A5 (https=) | 2005-12-02 |
| JP4346692B2 true JP4346692B2 (ja) | 2009-10-21 |
Family
ID=8228285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP54774698A Expired - Lifetime JP4346692B2 (ja) | 1997-05-02 | 1998-04-29 | 微生物バイオマスからのカロテノイド結晶の単離 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6812001B2 (https=) |
| EP (1) | EP0979302B1 (https=) |
| JP (1) | JP4346692B2 (https=) |
| AT (1) | ATE452203T1 (https=) |
| AU (1) | AU7530598A (https=) |
| DE (1) | DE69841382D1 (https=) |
| ES (1) | ES2337530T3 (https=) |
| RU (1) | RU2235783C2 (https=) |
| UA (1) | UA67742C2 (https=) |
| WO (1) | WO1998050574A1 (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2358862B (en) | 1999-12-21 | 2004-07-21 | Fermentron Ltd | Processes for Extracting Carotenoids from Biomass Carotenoid Sources |
| CA2397655C (en) * | 2000-01-19 | 2012-06-05 | Craig M. Ruecker | Solventless extraction process |
| US7015014B2 (en) | 2000-01-27 | 2006-03-21 | Dsm Ip Assets B.V. | Isolation of carotenoid crystals |
| ES2168971B1 (es) * | 2000-07-19 | 2003-11-01 | Antibioticos Sau | Procedimiento de produccion de beta-caroteno. |
| EP1178118A1 (en) | 2000-08-02 | 2002-02-06 | Dsm N.V. | Isolation of microbial oils |
| US20060234333A1 (en) * | 2003-01-09 | 2006-10-19 | Basf Aktiengesellschaft Patents, Trademarks And Licenses | Method for producing carotenoids or their precursors using genetically modified organisms of the blakeslea genus, carotenoids or their precursors produced by said method and use thereof |
| JP2004269663A (ja) * | 2003-03-07 | 2004-09-30 | Riken Vitamin Co Ltd | クロセチンの精製方法 |
| EP1866428A2 (en) | 2005-03-18 | 2007-12-19 | Microbia, Inc. | Production of carotenoids in oleaginous yeast and fungi |
| US20080020437A1 (en) * | 2006-07-20 | 2008-01-24 | Savarese John J | Apparatus and method for producing fuel ethanol from biomass |
| EP2078092A2 (en) | 2006-09-28 | 2009-07-15 | Microbia, Inc. | Production of carotenoids in oleaginous yeast and fungi |
| US20100145116A1 (en) * | 2007-03-08 | 2010-06-10 | Frederik Van Keulen | Production of High-Purity Carotenoids by Fermenting Selected Bacterial Strains |
| WO2010128957A1 (ru) * | 2009-05-05 | 2010-11-11 | Rasputin Vladimir Yurievich | Способ производства каротина кристаллического из водорослей, вегетирующих в соляных озерах |
| RU2421994C2 (ru) * | 2009-09-21 | 2011-06-27 | Государственное образовательное учреждение Высшего профессионального образования "Томский государственный университет" | Способ выделения минеральных зерен из жировой ткани |
| EP2571996B1 (en) | 2010-05-17 | 2017-03-08 | Dynadis Biotehc (India) Private Limited | Process for production of high purity beta-carotene and lycopene crystals from fungal biomass |
| EP2576801B1 (en) | 2010-06-01 | 2019-10-02 | DSM IP Assets B.V. | Extraction of lipid from cells and products therefrom |
| TWI414362B (zh) | 2011-05-18 | 2013-11-11 | Ind Tech Res Inst | 萃取裝置 |
| RU2475541C1 (ru) * | 2011-09-26 | 2013-02-20 | Федеральное государственное автономное образовательное учреждение высшего профессионального образования "ЮЖНЫЙ ФЕДЕРАЛЬНЫЙ УНИВЕРСИТЕТ" | СПОСОБ ПОЛУЧЕНИЯ ДЕИНОКСАНТИНА - КАРОТИНОИДА МИКРООРГАНИЗМА Deinococcus radiodurans |
| CN103012230A (zh) * | 2013-01-06 | 2013-04-03 | 大连医诺生物有限公司 | 三孢布拉霉菌中类胡萝卜素的高效提取新工艺 |
| FI3626806T3 (fi) | 2013-12-20 | 2024-08-22 | Mara Renewables Corp | Menetelmiä öljyn talteenottamiseksi mikro-organismeista |
| PL3083546T3 (pl) | 2013-12-20 | 2022-05-16 | Dsm Ip Assets B.V. | Sposoby wytwarzania oleju mikrobiologicznego z komórek mikrobiologicznych |
| AU2014369040B2 (en) | 2013-12-20 | 2019-12-05 | Dsm Ip Assets B.V. | Processes for obtaining microbial oil from microbial cells |
| CN105829539B (zh) | 2013-12-20 | 2023-11-10 | 帝斯曼营养品股份公司 | 从微生物中回收油的方法 |
| CN105939710B (zh) | 2013-12-20 | 2020-05-08 | 帝斯曼知识产权资产管理有限公司 | 用于从微生物细胞获得微生物油的方法 |
| NZ721413A (en) | 2013-12-20 | 2022-05-27 | Dsm Ip Assets Bv | Processes for obtaining microbial oil from microbial cells |
| AR098895A1 (es) | 2013-12-20 | 2016-06-22 | Dsm Ip Assets Bv | Proceso para obtener aceite microbiano a partir de células microbianas |
| CN104003920B (zh) * | 2014-06-13 | 2016-01-20 | 华侨大学 | 绿色环保制备不产氧光合细菌类胡萝卜素的方法 |
| CN107827798B (zh) * | 2017-11-21 | 2020-05-08 | 嘉必优生物技术（武汉）股份有限公司 | 一种β-胡萝卜素及其制备方法、应用 |
| US20240216321A1 (en) | 2022-12-02 | 2024-07-04 | Dsm Ip Assets B.V. | Fermentatively-produced retinoid containing compositions, and the methdos of making and using the same |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3226302A (en) * | 1963-05-15 | 1965-12-28 | Ciegler Alex | Production of beta-carotene |
| NL126583C (https=) * | 1963-07-19 | |||
| US3268606A (en) * | 1963-09-27 | 1966-08-23 | Upjohn Co | Beta-carotene process |
| US3492202A (en) * | 1967-12-12 | 1970-01-27 | Pfizer & Co C | Process for the production of beta-carotene |
| RU1028064C (ru) * | 1981-08-03 | 1994-12-15 | АО "Экотех" | СПОСОБ ПОЛУЧЕНИЯ МАСЛЯНОГО ПРЕПАРАТА β -КАРОТИНА |
| CN1033912C (zh) * | 1992-09-22 | 1997-01-29 | 南京师范大学 | 天然β-胡萝卜素顺、反异构体的分离方法 |
| CN1034730C (zh) * | 1992-09-29 | 1997-04-30 | 南京师范大学 | 盐藻的收集与β-胡萝卜素的提取方法 |
| ZA94614B (en) * | 1993-02-11 | 1994-08-12 | Sasol Chem Ind Pty | Solvent extraction |
| RU2112808C1 (ru) * | 1995-10-24 | 1998-06-10 | Акционерное общество открытого типа "Уралбиофарм" | Способ получения кристаллического бета-каротина |
| AU3696197A (en) * | 1996-07-19 | 1998-02-10 | Gist-Brocades B.V. | Process for the recovery of crystalline beta-carotene from natural source |
-
1998
- 1998-04-29 JP JP54774698A patent/JP4346692B2/ja not_active Expired - Lifetime
- 1998-04-29 AT AT98922804T patent/ATE452203T1/de not_active IP Right Cessation
- 1998-04-29 WO PCT/EP1998/002782 patent/WO1998050574A1/en not_active Ceased
- 1998-04-29 EP EP98922804A patent/EP0979302B1/en not_active Expired - Lifetime
- 1998-04-29 DE DE69841382T patent/DE69841382D1/de not_active Expired - Lifetime
- 1998-04-29 AU AU75305/98A patent/AU7530598A/en not_active Abandoned
- 1998-04-29 UA UA99126550A patent/UA67742C2/uk unknown
- 1998-04-29 RU RU99125609/13A patent/RU2235783C2/ru active
- 1998-04-29 ES ES98922804T patent/ES2337530T3/es not_active Expired - Lifetime
-
2001
- 2001-12-20 US US10/029,316 patent/US6812001B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69841382D1 (de) | 2010-01-28 |
| US6812001B2 (en) | 2004-11-02 |
| ES2337530T3 (es) | 2010-04-26 |
| JP2001523966A (ja) | 2001-11-27 |
| RU2235783C2 (ru) | 2004-09-10 |
| UA67742C2 (uk) | 2004-07-15 |
| EP0979302B1 (en) | 2009-12-16 |
| EP0979302A1 (en) | 2000-02-16 |
| WO1998050574A1 (en) | 1998-11-12 |
| AU7530598A (en) | 1998-11-27 |
| ATE452203T1 (de) | 2010-01-15 |
| US20020055135A1 (en) | 2002-05-09 |
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