EP1163329A2 - Surfactant-lipase complex immobilized on insoluble matrix - Google Patents
Surfactant-lipase complex immobilized on insoluble matrixInfo
- Publication number
- EP1163329A2 EP1163329A2 EP00911221A EP00911221A EP1163329A2 EP 1163329 A2 EP1163329 A2 EP 1163329A2 EP 00911221 A EP00911221 A EP 00911221A EP 00911221 A EP00911221 A EP 00911221A EP 1163329 A2 EP1163329 A2 EP 1163329A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- lipase
- surfactant
- group
- immobilized
- preparation
- 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.)
- Withdrawn
Links
- 239000004367 Lipase Substances 0.000 title claims abstract description 342
- 239000011159 matrix material Substances 0.000 title claims abstract description 76
- 102000004882 Lipase Human genes 0.000 claims abstract description 336
- 108090001060 Lipase Proteins 0.000 claims abstract description 336
- 235000019421 lipase Nutrition 0.000 claims abstract description 335
- 239000004094 surface-active agent Substances 0.000 claims abstract description 116
- 238000000034 method Methods 0.000 claims abstract description 89
- 238000002360 preparation method Methods 0.000 claims abstract description 65
- 229940040461 lipase Drugs 0.000 claims description 298
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 121
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- 229940088598 enzyme Drugs 0.000 claims description 89
- 238000006243 chemical reaction Methods 0.000 claims description 56
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 54
- 239000000194 fatty acid Substances 0.000 claims description 54
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- 150000004665 fatty acids Chemical class 0.000 claims description 51
- 238000009884 interesterification Methods 0.000 claims description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 42
- 238000005886 esterification reaction Methods 0.000 claims description 40
- 239000003921 oil Substances 0.000 claims description 36
- 235000019198 oils Nutrition 0.000 claims description 36
- 239000000243 solution Substances 0.000 claims description 35
- 230000032050 esterification Effects 0.000 claims description 34
- 150000003626 triacylglycerols Chemical class 0.000 claims description 34
- 238000006136 alcoholysis reaction Methods 0.000 claims description 31
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- 238000005809 transesterification reaction Methods 0.000 claims description 27
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 claims description 27
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 14
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- 229920003303 ion-exchange polymer Polymers 0.000 claims description 14
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 claims description 13
- 229930006000 Sucrose Natural products 0.000 claims description 12
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- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 claims description 7
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- 241001661345 Moesziomyces antarcticus Species 0.000 claims description 5
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 5
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 5
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- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 3
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- 238000001179 sorption measurement Methods 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 102000005744 Glycoside Hydrolases Human genes 0.000 description 2
- 108010031186 Glycoside Hydrolases Proteins 0.000 description 2
- 102100027329 Malonyl-CoA-acyl carrier protein transacylase, mitochondrial Human genes 0.000 description 2
- 101710137760 Malonyl-CoA-acyl carrier protein transacylase, mitochondrial Proteins 0.000 description 2
- 241000498617 Mucor javanicus Species 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004365 Protease Substances 0.000 description 2
- 239000004147 Sorbitan trioleate Substances 0.000 description 2
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 2
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- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 229940079919 digestives enzyme preparation Drugs 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 150000002190 fatty acyls Chemical group 0.000 description 2
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- 125000001165 hydrophobic group Chemical group 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
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- 235000010445 lecithin Nutrition 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000000527 sonication Methods 0.000 description 2
- 235000019337 sorbitan trioleate Nutrition 0.000 description 2
- 229960000391 sorbitan trioleate Drugs 0.000 description 2
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 238000009010 Bradford assay Methods 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 244000165918 Eucalyptus papuana Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 101710098556 Lipase A Proteins 0.000 description 1
- 101710099648 Lysosomal acid lipase/cholesteryl ester hydrolase Proteins 0.000 description 1
- 102100026001 Lysosomal acid lipase/cholesteryl ester hydrolase Human genes 0.000 description 1
- 101100412856 Mus musculus Rhod gene Proteins 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 235000007413 Nigella arvensis Nutrition 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 description 1
- 240000001058 Sterculia urens Species 0.000 description 1
- 235000015125 Sterculia urens Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 230000004641 brain development Effects 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000009885 chemical interesterification Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000009886 enzymatic interesterification Methods 0.000 description 1
- 239000003248 enzyme activator Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000001924 fatty-acyl group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
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- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229920000591 gum Polymers 0.000 description 1
- 230000007407 health benefit Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000002316 solid fats Nutrition 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
- C12N11/02—Enzymes or microbial cells immobilised on or in an organic carrier
- C12N11/08—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a synthetic polymer
- C12N11/082—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a synthetic polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C12N11/087—Acrylic polymers
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
- C12N9/18—Carboxylic ester hydrolases (3.1.1)
- C12N9/20—Triglyceride splitting, e.g. by means of lipase
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
- C12N11/02—Enzymes or microbial cells immobilised on or in an organic carrier
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
- C12N11/02—Enzymes or microbial cells immobilised on or in an organic carrier
- C12N11/08—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a synthetic polymer
- C12N11/082—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a synthetic polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
- C12N11/02—Enzymes or microbial cells immobilised on or in an organic carrier
- C12N11/08—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a synthetic polymer
- C12N11/089—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a synthetic polymer obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
- C12N11/14—Enzymes or microbial cells immobilised on or in an inorganic carrier
-
- 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
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6454—Glycerides by esterification
-
- 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
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6458—Glycerides by transesterification, e.g. interesterification, ester interchange, alcoholysis or acidolysis
-
- 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
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6472—Glycerides containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone
Definitions
- the present invention relates to an insoluble matrix immobilized
- surfactant-coated lipase complex to a method of preparing same and to the
- procedures include two steps.
- the enzyme is activated by
- the enzyme is immobilized
- alkoxide or cobalt chloride that catalyze acyl migration among triglyceride
- Lipases with 1,3 -positional specificity principally catalyze hydrolysis of fats
- lipases with 1,3 -positional specificity are also capable of catalyzing
- reaction is trans-esterification in which two different triglyceride molecules
- lipases At high concentrations of water, e.g., above 5 % of solvent weight, lipases
- cocoa butter substitute simulated human milk fat
- cardiovascular disease cardiovascular disease, immune disorders and inflammation, allergies,
- diabetes diabetes, kidney diseases, depression, brain development and cancer.
- medium-chain fatty acids incorporated into the same triglyceride molecule are of major importance in some clinical uses, especially,
- organic media e.g., Basheer, S., Mogi, K., Nakajima, M., 1995, Process.
- Biochemistry 30: 531-536 were included fixed- and fluidized-bed reactors,
- inorganic matrix was used both in a batch reactor system, and in fixed-bed
- Yet a further purpose of the invention is to provide a process for preparing
- the invention is primarily directed to a lipase preparation comprising an
- the immobilization of the lipase complex onto the insoluble matrix may be any immobilization of the lipase complex onto the insoluble matrix.
- the surfactant-coated lipase complex is covalently,
- the invention encompasses the use of many types of matrix, said matrices
- the inorganic insoluble matrix is
- alumina selected from the group consisting of alumina, diatomaceous earth, Celite,
- the abovementioned ion-exchange resin may be of any suitable material, but
- the organic insoluble matrix is selected from the
- the content of the lipase is 2-20 weight percent of
- the content of the lipase is 0.01-1.0 weight percent of the preparation.
- the invention provides the above-described lipase preparation, wherein the
- surfactant in the surfactant-coated lipase complex includes a fatty acid
- the fatty acid conjugated to a hydrophilic moiety.
- the fatty acid is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-(2-aminoethyl)-2-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N
- the hydrophilic moiety is selected from the group consisting of a
- the sugar is selected from the
- hydrophilic moiety may be linked by any suitable type of bond, in
- the fatty acid and the hydrophilic moiety are N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
- lipase may be derived or obtained from any convenient source
- the lipase is derived from a microorganism.
- Candida selected from a species selected from the group consisting of Burkholderia sp., Candida
- Candida rugosa Candida rugosa
- Pseudomonas sp. Candida antractica A
- the invention is directed to a lipase preparation
- the organic solvent is
- the invention is further directed to the use of said lipase preparation as a catalyst for esterification,
- the lipase triglycerols and fatty alcohols.
- the lipase triglycerols and fatty alcohols.
- the invention is directed to a lipase preparation as
- the invention also provides a lipase preparation, as described hereinabove,
- insoluble matrix has been modified with a fatty acid derivative.
- the invention is directed to an enzyme preparation, as
- the invention also encompasses a method for improving the stability of a
- surfactant-coated immobilized lipase complex comprising granulating same
- the invention provides a method of preparing an insoluble
- the lipase is first
- the lipase is first contacted with the lipase
- this method also further comprises the step of
- the drying step may be accomplished by any convenient method, in a
- said drying is effected by freeze drying.
- the matrix-immobilized surfactant-coated lipase is the matrix-immobilized surfactant-coated lipase
- lipase and surfactant are contacted in the aqueous medium by:
- the method further comprises sonication of
- insoluble matrix is selected from the group consisting of alumina,
- the surfactant of the method includes a
- said fatty acid is selected from the group consisting of monolaurate, monomyristate, monopalmitate, monostearate. dilaurate,
- dimyristate dipalmitate, distearate, trilaurate, trimyristate, tripalmitate and
- hydrophilic moiety is selected from the group consisting of a sugar and a
- the sugar is selected from the
- the lipase is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoe
- the lipase is
- the lipase may be
- the lipase is
- Candida antarctica B Candida rugosa, Pseudomonas sp., Candida antractica
- the invention is directed to a process for preparing
- surfactant-coated lipase complex is contacted with the substrates in the
- the oil is selected from the group consisting of:
- the fatty acid is selected from the group consisting of
- the fatty acid is selected from the group consisting of:
- oleic acid consisting of oleic acid, palmitic acid, linolic acid, linolenic acid, stearic acid,
- the invention also encompasses a triacylglycerol prepared according to the
- FIG. la presents an inter-esterification acidolysis reaction catalyzed by
- P represents glycerol bound palmitic
- C glycerol bound capric acid.
- PA and CA represent free
- FIG. lb presents a trans-esterification reaction catalyzed by lipase with
- FIG. 2 depicts the chemistry associated with covalent immobilization of
- FIG. 3 presents inter-esterification reaction profiles of physically
- reaction system was magnetically stirred and thermostated at 40 °C.
- FIG. 4 presents an Arrhenius plot for the inter-esterification reaction of
- FIG. 5 is a bar graph showing the functional stability of Lilipase A
- FIG. 6 is a bar graph showing the functional stability of powdered
- FIG. 7 is a bar graph showing the functional stability of Lilipase A
- FIG. 8 is a bar graph showing the functional stability of Lilipase A
- FIG. 9 is a bar graph showing the functional stability of Lilipase A
- FIG. 10 is a bar graph showing the functional stability of Lilipase A
- FIG. 11 is a bar graph showing the functional stability of Lilipase A
- FIG. 12 is a bar graph showing the functional stability of Lilipase A
- FIG. 13 is a bar graph showing the functional stability of Lilipase A
- FIG. 14 is a bar graph showing the functional stability of Lilipase A
- FIG. l ⁇ is a bar graph showing the functional stability of Lilipase A
- FIG. 16 is a bar graph showing the functional stability of Lilipase A
- the present invention relates to a surfactant-coated lipase or phospholipase
- particulate solid support which can be used to catalyze inter and
- the invention also makes provision for preparing the enzyme
- the present invention can be used for preparing
- the present invention is further directed to a method of preparing
- surfactant-coated lipases or phospholipases are provided.
- fatty acid sugar ester types lead to activation of the lipases for
- inorganic matrix showed high inter/trans-esterification activity and only
- present invention were produced by inter-esterification of long-chain
- triglycerides such as the hard fraction of palm oil, with short-chain fatty acids
- hydrolysis side reaction and their percentage was typically less than 7 weight
- liquid olive oil was
- a lipase preparation which includes an insoluble matrix and a
- surfactant-coated lipase complex immobilized onto the insoluble matrix.
- lipase is not limited to this specific enzyme, but is meant to embrace also
- the complex is immobilized to the
- insoluble matrix via hydrophobic (physical) interaction, ionic interaction or via
- inorganic insoluble matrix inorganic insoluble matrix
- solubility in both polar (e.g., water) and non-polar (hydrophobic) solvents e.g., water
- polar e.g., water
- non-polar hydrophobic
- the inorganic insoluble matrix according to the present invention is preferably, the inorganic insoluble matrix according to the present invention
- calcium sulfate, ion-exchange resin such as, but not limited to, Amberlite and
- DE diatomaceous earth
- the inorganic insoluble matrix employed is Amberlite and Dowex,
- Suitable organic solid matrices according to the present invention include
- the lipase represents 0.01-1 weight percent of the preparation.
- the lipase represents 0.01-1 weight percent of the preparation.
- lipase represents about 0.7 weight percent of the preparation.
- lipid which includes a fatty acid conjugated to a hydrophilic moiety.
- fatty acid is preferably monolaurate, monomyristate, monopalmitate,
- hydrophilic moiety is preferably
- a sugar such as, but not limited to, sorbitol, sucrose, glucose and lactose, a
- the fatty acid and the hydrophilic moiety are conjugated via an
- lipase extraction examples include Burkholderia sp., Candida antarctica B,
- Humicola sp. Mucor miehei, Rhizopus javan., Pseudomonas fluor, Candida
- Rhizopus japonicus and Candida antractica Rhizopus japonicus and Candida antractica.
- Lipase catalytic activity include hydrolysis, esterification, inter-esterification,
- the organic solvent is typically a
- hydrophobic solvent such as, but not limited to, n-hexane, toluene, iso-octane,
- n-octane benzene, cyclohexane and di-iso-propylether.
- the method includes the following method steps, wherein in a first step a
- lipase, an insoluble matrix and a surfactant are contacted in an aqueous
- surfactant-coated lipase is interacted with the matrix.
- the lipase is first interacted with the matrix and only thereafter the matrix
- immobilized lipase is interacted with the surfactant.
- the method further includes the step of
- drying is preferably effected via freeze drying, fluidization or
- complex preferably includes less than 100, more preferably less than 50, most
- solution is effected by dissolving the surfactant in an organic solvent (e.g.,
- the dissolved surfactant solution e.g., dropwise in the aqueous solution
- the lipase is first interacted with the
- hydrophobized carrier such as aluminium stearate, fatty-acid
- At least one of the substrates is an oil, a fatty acid
- the oil may be any of the above listed oils.
- the fatty acid may be any of the above listed oils.
- a medium or a short-chain fatty acid or an ester derivative thereof is a medium or a short-chain fatty acid or an ester derivative thereof.
- suitable fatty acid is, for example, oleic acid, palmitic acid, linolic acid,
- reaction reactor e.g., a tank reactor or a fixed-bed reactor.
- oils/fats e.g., triacylglycerols
- long-chain fatty alcohols (LCFAL) to produce wax esters by alcoholysis
- surfactant-coated lipase complex represents 2-30 weight percent of the
- oil/fat substrates are liquid
- oils and solid fats may be any of the above listed oils in a native or
- the triacylglycerol serves an
- esterification (inter- and trans-esterification), acidolysis, alcoholysis and hydrolysis catalytic activities with respect to substrates, yielding esterification
- hydrolysis products represent less
- Sorbitan fatty acid esters including
- Tris(Hydroxymethyl)aminomethane (tris) was from Sigma (USA). Inorganic
- organic matrices used as supports for the modified lipases include
- activators e.g. gum Arabic or polyethylene glycol.
- a typical enzyme e.g. gum Arabic or polyethylene glycol.
- the resulting enzyme solution was sonicated for 15min and then
- polypropylene, aluminium stearate or chitin) or inorganic matrix (20 g such
- formed powder can be directly used for batch enzymatic reactions or
- binding reagents such as starch, methyl or ethyl cellulose,
- resin used include: strong and week basic anion exchange resins,
- ion-exchange resins examples include: Dowex 22, Dowex
- the enzyme was primarily coated with a surfactant and then the
- lipase-surfactant complex was covalently linked to an Eupergit matrix, which
- enzyme preparations prepared according to this method contained 0.9 - 1.5 wt
- the esterification reaction was initiated by adding 10 mg lipase preparation
- the transesterification reaction was initiated by adding 10 mg lipase
- the alcoholysis reaction was initiated by adding 10 mg lipase preparation to
- immobilized lipases was determined by the microkejldahl method.
- insoluble matrix was tested using a 1ml vials containing the substrates.
- the vials were shaken at 40 °C and samples were analyzed after certain
- the protein content varied from 0.05 % to 1.12
- esterification transesterificatio ( ⁇ mol/min.mg ( ⁇ mol/min.mg n) protein) protein
- ⁇ mol/min.mg protein transesterificatio ( ⁇ mol/min.mg ( ⁇ mol/min.mg n) protein)
- Celite resulted in detectable levels of esterification and transesterification.
- Figure 3 presents the conversion of tripalmitin with time when
- the concentration of hydrolysis products did not exceed 5 wt % of
- fatty acids having longer alkyl chains such as palmitic and
- lipase complexes than fatty acids having shorter alkyl chains.
- Enzyme/Insoluble ri ri (transri matrix* (esterification) esterification) (alcoholysis) ( ⁇ molVmin.mg ( ⁇ mol/min.mg ( ⁇ mol/min.m protein) protein) g protein)
- fatty acid derivative-treated insoluble matrix (Aluminum monostearate, fatty acid derivative-treated Celite) is much greater than the activity of
- Fig. 5 shows that the activity of Lilipase A-10FG immobilized on Celite
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Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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IL12908699 | 1999-03-22 | ||
IL12908699A IL129086A0 (en) | 1999-03-22 | 1999-03-22 | Surfactant-lipase complex immobilized on insoluble matrix |
PCT/IL2000/000166 WO2000056869A2 (en) | 1999-03-22 | 2000-03-16 | Surfactant-lipase complex immobilized on insoluble matrix |
Publications (1)
Publication Number | Publication Date |
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EP1163329A2 true EP1163329A2 (en) | 2001-12-19 |
Family
ID=11072627
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP00911221A Withdrawn EP1163329A2 (en) | 1999-03-22 | 2000-03-16 | Surfactant-lipase complex immobilized on insoluble matrix |
Country Status (7)
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EP (1) | EP1163329A2 (ja) |
JP (1) | JP2002539782A (ja) |
KR (1) | KR100774281B1 (ja) |
CA (1) | CA2368179A1 (ja) |
IL (2) | IL129086A0 (ja) |
NZ (1) | NZ514271A (ja) |
WO (1) | WO2000056869A2 (ja) |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL142952A (en) | 2001-05-03 | 2005-12-18 | Enzmotec Ltd | Process for enzyme-catalyzed production of 1,2 diacylated phospholipids |
KR100485090B1 (ko) * | 2002-01-14 | 2005-04-22 | 주식회사 포스코 | 이온성 액체로 코팅된 효소 |
IL152290A0 (en) * | 2002-10-14 | 2003-05-29 | Enzymotec Ltd | Immobilization of compounds on polymeric matrix |
US20060233863A1 (en) | 2003-02-10 | 2006-10-19 | Enzymotec Ltd. | Oils enriched with diacylglycerols and phytosterol esters and unit dosage forms thereof for use in therapy |
IL158139A0 (en) | 2003-09-25 | 2004-09-27 | Enzymotec Ltd | Stabilized formulations of phosphatidyl serine |
US8052992B2 (en) | 2003-10-22 | 2011-11-08 | Enzymotec Ltd. | Glycerophospholipids containing omega-3 and omega-6 fatty acids and their use in the treatment and improvement of cognitive functions |
IL158555A0 (en) | 2003-10-22 | 2004-05-12 | Enzymotec Ltd | Human breast milk lipid mimetic as dietary supplement |
US20050130937A1 (en) | 2003-10-22 | 2005-06-16 | Enzymotec Ltd. | Lipids containing omega-3 and omega-6 fatty acids |
MY142014A (en) * | 2004-04-08 | 2010-08-16 | Nisshin Oillio Group Ltd | A lipase powder, methods for producing the same and use thereof |
WO2006016363A2 (en) | 2004-08-10 | 2006-02-16 | Enzymotec Ltd. | Mixture of phytosterol ester(s) and 1, 3-diglyceride(s) for use in the treatment of medical conditions |
US7473539B2 (en) * | 2004-09-20 | 2009-01-06 | Sunho Biodiesel Corporation | Methods for producing alkyl esters |
JP4785174B2 (ja) * | 2004-12-10 | 2011-10-05 | 株式会社豊田中央研究所 | 膜タンパク質複合材料及びその製造方法 |
EP2439268B1 (en) * | 2005-06-16 | 2015-11-04 | DSM Nutritional Products AG | Immobilized enzymes and methods of using thereof |
JP4917349B2 (ja) * | 2006-05-11 | 2012-04-18 | 日清オイリオグループ株式会社 | リパーゼ活性の回復方法 |
IL180598A0 (en) * | 2007-01-08 | 2007-07-04 | Basheer Sobhi | Immobilized interfacial enzymes of improved and stabilized activity |
IL183084A0 (en) | 2007-05-09 | 2007-09-20 | Trans Biodisel Ltd | Modified-immobilized enzymes of high tolerance to hydrophilic substrates in organic media |
DE102008006716A1 (de) * | 2008-01-30 | 2009-08-13 | BAM Bundesanstalt für Materialforschung und -prüfung | Lipasenformulierung |
US8846338B2 (en) | 2008-08-07 | 2014-09-30 | Lipogen Ltd. | Processes for the preparation of phosphatides |
DK2563167T3 (en) | 2010-04-26 | 2015-05-18 | Enzymotec Ltd | PRACTICES AND lipid TO PROMOTE DEVELOPMENT OF INTESTINAL FLORA |
EP3173464B1 (en) * | 2014-07-22 | 2021-11-24 | The Nisshin OilliO Group, Ltd. | Powdered fat/oil composition, food including powdered fat/oil composition, and methods for producing same |
WO2017051910A1 (ja) | 2015-09-24 | 2017-03-30 | 日清オイリオグループ株式会社 | 粉末油脂組成物及びその製造方法 |
JP6216098B1 (ja) | 2016-01-21 | 2017-10-18 | 日清オイリオグループ株式会社 | 液状成分の粉末化剤 |
JP6216099B1 (ja) | 2016-01-21 | 2017-10-18 | 日清オイリオグループ株式会社 | 液状成分の粉末化剤 |
EP3406683A4 (en) | 2016-01-21 | 2020-02-26 | The Nisshin OilliO Group, Ltd. | LIQUID COMPONENT THICKENER |
US11219224B2 (en) | 2016-01-21 | 2022-01-11 | The Nisshin Oillio Group, Ltd. | Thickener for liquid component |
Citations (2)
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---|---|---|---|---|
JPH0662859A (ja) * | 1992-08-20 | 1994-03-08 | Amano Pharmaceut Co Ltd | 固定化修飾酵素、該固定化修飾酵素を用いるエステル合成方法 |
JP2778135B2 (ja) * | 1989-07-18 | 1998-07-23 | 味の素株式会社 | リパーゼ固定化酵素剤の調製方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
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DK638688D0 (da) * | 1988-11-16 | 1988-11-16 | Novo Industri As | Partikelformet immobiliseret lipase-praeparat, fremgangsmaade til fremstilling deraf og anvendelse deraf |
ES2109698T3 (es) * | 1993-05-20 | 1998-01-16 | Loders Croklaan Bv | Procedimiento para la preparacion de lipasas inmovilizadas. |
JPH07135972A (ja) * | 1993-09-22 | 1995-05-30 | Ajinomoto Co Inc | リパーゼ酵素剤及び該リパーゼ酵素剤を用いる油脂の改質法 |
CN1266460A (zh) * | 1997-06-05 | 2000-09-13 | 卡尔金有限责任公司 | 二酰甘油酰基转移酶蛋白 |
EP0882798A1 (en) * | 1997-06-06 | 1998-12-09 | Akzo Nobel N.V. | Process for the preparation of a monoester-containing esterification product of a polyoxyalkylated sucrose |
AU8760898A (en) * | 1997-09-24 | 1999-04-12 | Enzymotec Ltd. | Surfactant-lipase complex immobilized on insoluble matrix |
-
1999
- 1999-03-22 IL IL12908699A patent/IL129086A0/xx unknown
-
2000
- 2000-03-16 KR KR1020017012028A patent/KR100774281B1/ko active IP Right Grant
- 2000-03-16 WO PCT/IL2000/000166 patent/WO2000056869A2/en active IP Right Grant
- 2000-03-16 JP JP2000606728A patent/JP2002539782A/ja active Pending
- 2000-03-16 EP EP00911221A patent/EP1163329A2/en not_active Withdrawn
- 2000-03-16 NZ NZ514271A patent/NZ514271A/en not_active IP Right Cessation
- 2000-03-16 CA CA002368179A patent/CA2368179A1/en not_active Abandoned
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2001
- 2001-09-17 IL IL145503A patent/IL145503A/en not_active IP Right Cessation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2778135B2 (ja) * | 1989-07-18 | 1998-07-23 | 味の素株式会社 | リパーゼ固定化酵素剤の調製方法 |
JPH0662859A (ja) * | 1992-08-20 | 1994-03-08 | Amano Pharmaceut Co Ltd | 固定化修飾酵素、該固定化修飾酵素を用いるエステル合成方法 |
Also Published As
Publication number | Publication date |
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IL129086A0 (en) | 2000-02-17 |
KR100774281B1 (ko) | 2007-11-08 |
WO2000056869A2 (en) | 2000-09-28 |
KR20020010129A (ko) | 2002-02-02 |
JP2002539782A (ja) | 2002-11-26 |
CA2368179A1 (en) | 2000-09-28 |
NZ514271A (en) | 2003-08-29 |
WO2000056869A3 (en) | 2001-02-08 |
IL145503A (en) | 2009-06-15 |
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