NO319671B1 - Enzymatiske syntese av kirale aminer samt fremgangsmate for fremstilling av (S)-1-metoksy-2-aminopropan - Google Patents
Enzymatiske syntese av kirale aminer samt fremgangsmate for fremstilling av (S)-1-metoksy-2-aminopropan Download PDFInfo
- Publication number
- NO319671B1 NO319671B1 NO20004036A NO20004036A NO319671B1 NO 319671 B1 NO319671 B1 NO 319671B1 NO 20004036 A NO20004036 A NO 20004036A NO 20004036 A NO20004036 A NO 20004036A NO 319671 B1 NO319671 B1 NO 319671B1
- Authority
- NO
- Norway
- Prior art keywords
- aminopropane
- amino
- methoxy
- transaminase
- chiral
- Prior art date
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- 150000001412 amines Chemical class 0.000 title claims abstract description 39
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 20
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 18
- NXMXETCTWNXSFG-BYPYZUCNSA-N (2s)-1-methoxypropan-2-amine Chemical compound COC[C@H](C)N NXMXETCTWNXSFG-BYPYZUCNSA-N 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims description 8
- 230000002255 enzymatic effect Effects 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 28
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims abstract description 27
- 108090000340 Transaminases Proteins 0.000 claims abstract description 20
- 102000003929 Transaminases Human genes 0.000 claims abstract description 20
- CUZLJOLBIRPEFB-UHFFFAOYSA-N 1-methoxypropan-2-one Chemical compound COCC(C)=O CUZLJOLBIRPEFB-UHFFFAOYSA-N 0.000 claims abstract description 10
- 230000000707 stereoselective effect Effects 0.000 claims abstract description 8
- 150000002576 ketones Chemical class 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 150000001413 amino acids Chemical class 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims 1
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- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 abstract description 11
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 abstract description 8
- 229940107700 pyruvic acid Drugs 0.000 abstract description 4
- 229910052799 carbon Inorganic materials 0.000 description 19
- 125000003277 amino group Chemical group 0.000 description 18
- 229940024606 amino acid Drugs 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 235000001014 amino acid Nutrition 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 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 12
- -1 2-methylbutane-1,4-diyl Chemical group 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 235000007682 pyridoxal 5'-phosphate Nutrition 0.000 description 7
- 239000011589 pyridoxal 5'-phosphate Substances 0.000 description 7
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- 125000000217 alkyl group Chemical group 0.000 description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
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- 229910052757 nitrogen Inorganic materials 0.000 description 4
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229960002684 aminocaproic acid Drugs 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- BTNMPGBKDVTSJY-UHFFFAOYSA-N keto-phenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=CC=C1 BTNMPGBKDVTSJY-UHFFFAOYSA-N 0.000 description 2
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- 239000008363 phosphate buffer Substances 0.000 description 2
- ISYORFGKSZLPNW-UHFFFAOYSA-N propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH3+] ISYORFGKSZLPNW-UHFFFAOYSA-N 0.000 description 2
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- PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- IOLQWLOHKZENDW-UHFFFAOYSA-N phenylisobutylamine Chemical compound CCC(N)CC1=CC=CC=C1 IOLQWLOHKZENDW-UHFFFAOYSA-N 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 235000008151 pyridoxamine Nutrition 0.000 description 1
- 239000011699 pyridoxamine Substances 0.000 description 1
- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- SUAMAHKUSIHRMR-UHFFFAOYSA-M sodium;2-oxobutanoate Chemical compound [Na+].CCC(=O)C([O-])=O SUAMAHKUSIHRMR-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction 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
- 229960003080 taurine Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 239000004474 valine 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
- C12P13/001—Amines; Imines
-
- 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
-
- 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
- C12P13/005—Amino acids other than alpha- or beta amino acids, e.g. gamma 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
- 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/06—Alanine; Leucine; Isoleucine; Serine; Homoserine
-
- 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
- C12P13/12—Methionine; Cysteine; Cystine
-
- 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
- C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Genetics & Genomics (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7752098P | 1998-03-11 | 1998-03-11 | |
| PCT/US1999/005150 WO1999046398A1 (en) | 1998-03-11 | 1999-03-10 | Improvements in the enzymatic synthesis of chiral amines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20004036D0 NO20004036D0 (no) | 2000-08-11 |
| NO20004036L NO20004036L (no) | 2000-10-27 |
| NO319671B1 true NO319671B1 (no) | 2005-09-05 |
Family
ID=22138554
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20004036A NO319671B1 (no) | 1998-03-11 | 2000-08-11 | Enzymatiske syntese av kirale aminer samt fremgangsmate for fremstilling av (S)-1-metoksy-2-aminopropan |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP1075534B8 (sk) |
| JP (1) | JP2002505884A (sk) |
| KR (1) | KR20010034561A (sk) |
| CN (1) | CN1154746C (sk) |
| AT (1) | ATE295424T1 (sk) |
| AU (1) | AU753904B2 (sk) |
| BR (1) | BR9908797A (sk) |
| CA (1) | CA2322605A1 (sk) |
| CZ (1) | CZ295882B6 (sk) |
| DE (1) | DE69925267T2 (sk) |
| ES (1) | ES2243051T3 (sk) |
| FI (1) | FI20001805A (sk) |
| HK (1) | HK1035000A1 (sk) |
| HU (1) | HUP0101056A3 (sk) |
| MX (1) | MXPA00008573A (sk) |
| NO (1) | NO319671B1 (sk) |
| NZ (1) | NZ506405A (sk) |
| PL (1) | PL342882A1 (sk) |
| PT (1) | PT1075534E (sk) |
| RU (1) | RU2213142C2 (sk) |
| SK (1) | SK284352B6 (sk) |
| TR (1) | TR200002604T2 (sk) |
| UA (1) | UA64784C2 (sk) |
| WO (1) | WO1999046398A1 (sk) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60013939T2 (de) | 1999-03-19 | 2005-10-06 | Sumitomo Chemical Co. Ltd. | Stereoselektive Transaminase, deren kodierende Gen und deren Verwendungen |
| JP2001190298A (ja) * | 2000-01-13 | 2001-07-17 | Kanegafuchi Chem Ind Co Ltd | 光学活性ｎ−メチルアミノ酸の製造方法 |
| EP1818411A1 (en) * | 2006-02-13 | 2007-08-15 | Lonza AG | Process for the preparation of optically active chiral amines |
| DE102007042600A1 (de) | 2007-09-07 | 2009-03-12 | Evonik Degussa Gmbh | Verfahren zur Herstellung von enantiomerenangereichten Aminen |
| DK3354727T3 (da) | 2009-01-08 | 2020-11-16 | Codexis Inc | Transaminasepolypeptider |
| EP2401366B1 (en) | 2009-02-26 | 2013-12-18 | Codexis, Inc. | Transaminase biocatalysts |
| WO2011005477A1 (en) | 2009-06-22 | 2011-01-13 | Codexis, Inc. | Transaminase reactions |
| EP2857505B1 (en) * | 2009-09-02 | 2016-10-19 | Lonza AG | A process for the identification and preparation of a (R)-specific omega-transaminase |
| US8852900B2 (en) | 2010-06-17 | 2014-10-07 | Codexis, Inc. | Biocatalysts and methods for the synthesis of (S)-3-(1-aminoethyl)-phenol |
| WO2012024104A2 (en) | 2010-08-16 | 2012-02-23 | Codexis, Inc. | Biocatalysts and methods for the synthesis of (1r,2r)-2-(3,4-dimethoxyphenethoxy)cyclohexanamine |
| JP6275642B2 (ja) * | 2011-08-16 | 2018-02-07 | エンバイオ・リミテツド | 光学活性キラルアミンの酵素的合成 |
| CN104630170A (zh) * | 2013-11-08 | 2015-05-20 | 中国科学院天津工业生物技术研究所 | 一种来源于里氏木霉的新(r)-转氨酶及其应用 |
| CN114134126B (zh) * | 2021-10-28 | 2023-12-05 | 浙江大学杭州国际科创中心 | 转氨酶及其突变体在制备(s)-1-甲氧基-2-丙胺中的应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5300437A (en) * | 1989-06-22 | 1994-04-05 | Celgene Corporation | Enantiomeric enrichment and stereoselective synthesis of chiral amines |
| DE69635082T2 (de) * | 1995-10-23 | 2006-06-01 | Kaneka Corp. | Verfahren zur herstellung optisch aktiver aminoverbindungen |
-
1999
- 1999-03-10 SK SK1338-2000A patent/SK284352B6/sk unknown
- 1999-03-10 NZ NZ506405A patent/NZ506405A/en not_active IP Right Cessation
- 1999-03-10 RU RU2000125535/13A patent/RU2213142C2/ru active IP Right Revival
- 1999-03-10 DE DE69925267T patent/DE69925267T2/de not_active Expired - Fee Related
- 1999-03-10 TR TR2000/02604T patent/TR200002604T2/xx unknown
- 1999-03-10 WO PCT/US1999/005150 patent/WO1999046398A1/en active IP Right Grant
- 1999-03-10 AU AU29938/99A patent/AU753904B2/en not_active Ceased
- 1999-03-10 PT PT99911250T patent/PT1075534E/pt unknown
- 1999-03-10 AT AT99911250T patent/ATE295424T1/de not_active IP Right Cessation
- 1999-03-10 CZ CZ20003177A patent/CZ295882B6/cs not_active IP Right Cessation
- 1999-03-10 CN CNB99803651XA patent/CN1154746C/zh not_active Expired - Fee Related
- 1999-03-10 EP EP99911250A patent/EP1075534B8/en not_active Expired - Lifetime
- 1999-03-10 ES ES99911250T patent/ES2243051T3/es not_active Expired - Lifetime
- 1999-03-10 PL PL99342882A patent/PL342882A1/xx not_active IP Right Cessation
- 1999-03-10 BR BR9908797-9A patent/BR9908797A/pt not_active IP Right Cessation
- 1999-03-10 JP JP2000535765A patent/JP2002505884A/ja not_active Withdrawn
- 1999-03-10 HU HU0101056A patent/HUP0101056A3/hu unknown
- 1999-03-10 CA CA002322605A patent/CA2322605A1/en not_active Abandoned
- 1999-03-10 KR KR1020007009945A patent/KR20010034561A/ko active IP Right Grant
- 1999-03-10 MX MXPA00008573A patent/MXPA00008573A/es active IP Right Grant
- 1999-10-03 UA UA2000105759A patent/UA64784C2/uk unknown
-
2000
- 2000-08-11 NO NO20004036A patent/NO319671B1/no unknown
- 2000-08-15 FI FI20001805A patent/FI20001805A/fi not_active IP Right Cessation
-
2001
- 2001-08-09 HK HK01105536A patent/HK1035000A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PL342882A1 (en) | 2001-07-16 |
| PT1075534E (pt) | 2005-09-30 |
| EP1075534A4 (en) | 2003-07-09 |
| FI20001805A (fi) | 2000-08-15 |
| NO20004036L (no) | 2000-10-27 |
| NZ506405A (en) | 2003-08-29 |
| TR200002604T2 (tr) | 2000-11-21 |
| DE69925267D1 (de) | 2005-06-16 |
| BR9908797A (pt) | 2000-12-12 |
| EP1075534A1 (en) | 2001-02-14 |
| NO20004036D0 (no) | 2000-08-11 |
| EP1075534B8 (en) | 2005-07-06 |
| ATE295424T1 (de) | 2005-05-15 |
| SK13382000A3 (sk) | 2001-05-10 |
| EP1075534B1 (en) | 2005-05-11 |
| HUP0101056A3 (en) | 2006-03-28 |
| ES2243051T3 (es) | 2005-11-16 |
| RU2213142C2 (ru) | 2003-09-27 |
| SK284352B6 (sk) | 2005-02-04 |
| HK1035000A1 (en) | 2001-11-09 |
| AU2993899A (en) | 1999-09-27 |
| MXPA00008573A (es) | 2003-07-14 |
| DE69925267T2 (de) | 2006-01-26 |
| AU753904B2 (en) | 2002-10-31 |
| CN1292828A (zh) | 2001-04-25 |
| HUP0101056A2 (hu) | 2001-07-30 |
| UA64784C2 (en) | 2004-03-15 |
| CZ295882B6 (cs) | 2005-11-16 |
| CZ20003177A3 (cs) | 2000-12-13 |
| CN1154746C (zh) | 2004-06-23 |
| WO1999046398A1 (en) | 1999-09-16 |
| KR20010034561A (ko) | 2001-04-25 |
| CA2322605A1 (en) | 1999-09-16 |
| JP2002505884A (ja) | 2002-02-26 |
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