CA2805997A1 - Galacto-oligosaccharide-containing composition and a method of producing it - Google Patents
Galacto-oligosaccharide-containing composition and a method of producing it Download PDFInfo
- Publication number
- CA2805997A1 CA2805997A1 CA2805997A CA2805997A CA2805997A1 CA 2805997 A1 CA2805997 A1 CA 2805997A1 CA 2805997 A CA2805997 A CA 2805997A CA 2805997 A CA2805997 A CA 2805997A CA 2805997 A1 CA2805997 A1 CA 2805997A1
- Authority
- CA
- Canada
- Prior art keywords
- gal
- galactosyl
- enzyme
- amino acid
- galacto
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 138
- 235000021255 galacto-oligosaccharides Nutrition 0.000 title claims abstract description 107
- 150000003271 galactooligosaccharides Chemical class 0.000 title claims abstract description 107
- 238000000034 method Methods 0.000 title claims abstract description 54
- 125000002519 galactosyl group Chemical group C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 claims description 224
- 102000004190 Enzymes Human genes 0.000 claims description 133
- 108090000790 Enzymes Proteins 0.000 claims description 133
- 125000003275 alpha amino acid group Chemical group 0.000 claims description 72
- GUBGYTABKSRVRQ-QKKXKWKRSA-N lactose group Chemical group OC1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@H](O2)CO)[C@H](O1)CO GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 45
- 239000008101 lactose Substances 0.000 claims description 38
- 108010005774 beta-Galactosidase Proteins 0.000 claims description 22
- 230000000694 effects Effects 0.000 claims description 22
- 125000003147 glycosyl group Chemical group 0.000 claims description 21
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 20
- 238000003556 assay Methods 0.000 claims description 11
- 150000005846 sugar alcohols Chemical class 0.000 claims description 7
- 238000012546 transfer Methods 0.000 claims description 5
- 239000000832 lactitol Substances 0.000 claims description 3
- VQHSOMBJVWLPSR-JVCRWLNRSA-N lactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-JVCRWLNRSA-N 0.000 claims description 3
- 235000010448 lactitol Nutrition 0.000 claims description 3
- 229960003451 lactitol Drugs 0.000 claims description 3
- 238000001728 nano-filtration Methods 0.000 claims description 3
- 238000013375 chromatographic separation Methods 0.000 claims description 2
- 102000005936 beta-Galactosidase Human genes 0.000 claims 2
- 125000000837 carbohydrate group Chemical group 0.000 claims 1
- 229940088598 enzyme Drugs 0.000 description 125
- 239000000370 acceptor Substances 0.000 description 103
- 229960001375 lactose Drugs 0.000 description 37
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 33
- 229920001542 oligosaccharide Polymers 0.000 description 33
- 150000002482 oligosaccharides Chemical class 0.000 description 29
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 24
- 229930182830 galactose Natural products 0.000 description 23
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 21
- 238000006911 enzymatic reaction Methods 0.000 description 21
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- 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 description 17
- 238000004128 high performance liquid chromatography Methods 0.000 description 15
- 150000001720 carbohydrates Chemical class 0.000 description 14
- 230000008569 process Effects 0.000 description 14
- 150000004043 trisaccharides Chemical class 0.000 description 14
- SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 13
- 239000000047 product Substances 0.000 description 11
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- SHZGCJCMOBCMKK-PQMKYFCFSA-N L-Fucose Natural products C[C@H]1O[C@H](O)[C@@H](O)[C@@H](O)[C@@H]1O SHZGCJCMOBCMKK-PQMKYFCFSA-N 0.000 description 10
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- 238000012512 characterization method Methods 0.000 description 10
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- -1 FOS Chemical class 0.000 description 9
- SRBFZHDQGSBBOR-IOVATXLUSA-N Xylose Natural products O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 9
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 9
- 150000002016 disaccharides Chemical class 0.000 description 9
- 108090000765 processed proteins & peptides Proteins 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 7
- 150000001719 carbohydrate derivatives Chemical class 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- SHZGCJCMOBCMKK-SVZMEOIVSA-N D-fucopyranose Chemical compound C[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O SHZGCJCMOBCMKK-SVZMEOIVSA-N 0.000 description 6
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- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 5
- OVRNDRQMDRJTHS-CBQIKETKSA-N N-Acetyl-D-Galactosamine Chemical group CC(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@H](O)[C@@H]1O OVRNDRQMDRJTHS-CBQIKETKSA-N 0.000 description 5
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- 238000010923 batch production Methods 0.000 description 5
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- 235000013365 dairy product Nutrition 0.000 description 5
- 230000002255 enzymatic effect Effects 0.000 description 5
- 150000002402 hexoses Chemical class 0.000 description 5
- 229960001021 lactose monohydrate Drugs 0.000 description 5
- 239000007790 solid phase Substances 0.000 description 5
- 125000000969 xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 description 5
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 4
- 108091028043 Nucleic acid sequence Proteins 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- 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 description 4
- 108010046377 Whey Proteins Proteins 0.000 description 4
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- 238000013459 approach Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 4
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 4
- 150000002772 monosaccharides Chemical class 0.000 description 4
- 150000002972 pentoses Chemical class 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- 229960003487 xylose Drugs 0.000 description 4
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PNNNRSAQSRJVSB-SLPGGIOYSA-N Fucose Natural products C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-SLPGGIOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229920001202 Inulin Polymers 0.000 description 3
- 108010059881 Lactase Proteins 0.000 description 3
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- 239000005862 Whey Substances 0.000 description 3
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- 150000001413 amino acids Chemical class 0.000 description 3
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- 229960003082 galactose Drugs 0.000 description 3
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Classifications
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- 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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/02—Monosaccharides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
- A23L33/21—Addition of substantially indigestible substances, e.g. dietary fibres
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/40—Complete food formulations for specific consumer groups or specific purposes, e.g. infant formula
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/04—Disaccharides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- 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)
- C12N9/24—Hydrolases (3) acting on glycosyl compounds (3.2)
- C12N9/2402—Hydrolases (3) acting on glycosyl compounds (3.2) hydrolysing O- and S- glycosyl compounds (3.2.1)
- C12N9/2468—Hydrolases (3) acting on glycosyl compounds (3.2) hydrolysing O- and S- glycosyl compounds (3.2.1) acting on beta-galactose-glycoside bonds, e.g. carrageenases (3.2.1.83; 3.2.1.157); beta-agarase (3.2.1.81)
-
- 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)
- C12N9/24—Hydrolases (3) acting on glycosyl compounds (3.2)
- C12N9/2402—Hydrolases (3) acting on glycosyl compounds (3.2) hydrolysing O- and S- glycosyl compounds (3.2.1)
- C12N9/2468—Hydrolases (3) acting on glycosyl compounds (3.2) hydrolysing O- and S- glycosyl compounds (3.2.1) acting on beta-galactose-glycoside bonds, e.g. carrageenases (3.2.1.83; 3.2.1.157); beta-agarase (3.2.1.81)
- C12N9/2471—Beta-galactosidase (3.2.1.23), i.e. exo-(1-->4)-beta-D-galactanase
-
- 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
- C12P19/00—Preparation of compounds containing saccharide radicals
-
- 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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/12—Disaccharides
-
- 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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/14—Preparation of compounds containing saccharide radicals produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase, e.g. by cellulase, hemicellulase
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y302/00—Hydrolases acting on glycosyl compounds, i.e. glycosylases (3.2)
- C12Y302/01—Glycosidases, i.e. enzymes hydrolysing O- and S-glycosyl compounds (3.2.1)
- C12Y302/01023—Beta-galactosidase (3.2.1.23), i.e. exo-(1-->4)-beta-D-galactanase
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Mycology (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Pediatric Medicine (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (5)
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| US36556010P | 2010-07-19 | 2010-07-19 | |
| EP10169981.7 | 2010-07-19 | ||
| EP10169981 | 2010-07-19 | ||
| US61/365,560 | 2010-07-19 | ||
| PCT/EP2011/062355 WO2012010597A1 (en) | 2010-07-19 | 2011-07-19 | Galacto-oligosaccharide-containing composition and a method of producing it |
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| CA2805997A1 true CA2805997A1 (en) | 2012-01-26 |
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| CA2805997A Abandoned CA2805997A1 (en) | 2010-07-19 | 2011-07-19 | Galacto-oligosaccharide-containing composition and a method of producing it |
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| EP2620506A1 (en) | 2012-01-25 | 2013-07-31 | Arla Foods Amba | Method of producing a galacto-oligosaccharide-containing composition |
| EP3473714B1 (en) * | 2012-06-08 | 2022-04-06 | DuPont Nutrition Biosciences ApS | Polypeptides having transgalactosylating activity |
| WO2013190530A1 (en) * | 2012-06-22 | 2013-12-27 | Glycom A/S | Modified galactooligosaccharides |
| CA2913393A1 (en) | 2013-05-24 | 2014-11-27 | General Mills, Inc. | Food products with yogurt whey |
| WO2015086746A1 (en) | 2013-12-11 | 2015-06-18 | Dupont Nutrition Biosciences Aps | A method for preparing a dairy product having a stable content of galacto-oligosaccharide(s) |
| KR101595014B1 (ko) | 2014-02-21 | 2016-02-18 | 재단법인 임실치즈과학연구소 | 갈락토올리고당 생성 유산균주를 이용한 발효유의 제조방법 |
| EP3915384A1 (en) | 2014-11-07 | 2021-12-01 | DuPont Nutrition Biosciences ApS | Recombinant host cell expressing beta-galactosidase and/or transgalactosylating activity deficient in cellulase |
| JP6851967B2 (ja) * | 2014-11-07 | 2021-03-31 | デュポン ニュートリション バイオサイエンシス エーピーエス | トランスガラクトシル化活性を有する酵素を用いてガラクトースとフルクトース部分とを含むサッカリドを生成する方法 |
| DK3607097T3 (da) | 2017-04-07 | 2023-09-18 | Dupont Nutrition Biosci Aps | Bacillus-værtsceller, der danner beta-galactosidaser og lactaser i fravær af p-nitrobenzylesterase-sideaktivitet |
| GB201805577D0 (en) * | 2018-04-04 | 2018-05-16 | Optibiotix Health Ltd | Prebiotic compositions and methods of production thereof |
| WO2023055902A1 (en) | 2021-09-30 | 2023-04-06 | Dupont Nutrition Biosciences Aps | Method for reducing sugar in food stuff |
| US20250000113A1 (en) | 2021-11-12 | 2025-01-02 | Kerry Group Services International Ltd | Method for producing a dairy product |
| AU2024242918A1 (en) | 2023-03-29 | 2025-09-18 | Danisco Us Inc. | Methods for modifying texture in foodstuff via preferably in situ produced alpha-glucan |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1283876B1 (en) * | 2000-05-26 | 2007-01-24 | Arla Foods amba | Beta-galactosidase isolated from bifidobacterium |
| EP1205555A1 (de) * | 2000-11-08 | 2002-05-15 | Solvent Innovation GmbH | Enzymkatalyse in Gegenwart ionischer Flüssigkeiten |
| MXPA05010349A (es) * | 2003-06-30 | 2006-03-08 | Clasado Inc | Composicion novedosa de galactooligosacaridos y preparacion de la misma. |
| GB0522740D0 (en) * | 2005-11-08 | 2005-12-14 | Clasado Inc | Process for the production of oligosaccharides |
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- 2011-07-19 MX MX2013000793A patent/MX348325B/es active IP Right Grant
- 2011-07-19 EA EA201300150A patent/EA201300150A1/ru unknown
- 2011-07-19 WO PCT/EP2011/062355 patent/WO2012010597A1/en not_active Ceased
- 2011-07-19 NZ NZ607149A patent/NZ607149A/en not_active IP Right Cessation
- 2011-07-19 EP EP11734090.1A patent/EP2596113B1/en active Active
- 2011-07-19 US US13/811,171 patent/US20130189746A1/en not_active Abandoned
- 2011-07-19 CN CN201180035455.1A patent/CN103080329B/zh not_active Expired - Fee Related
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2016
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| Publication number | Publication date |
|---|---|
| WO2012010597A1 (en) | 2012-01-26 |
| US20130189746A1 (en) | 2013-07-25 |
| EA201300150A1 (ru) | 2013-08-30 |
| MX2013000793A (es) | 2014-04-30 |
| NZ607149A (en) | 2014-12-24 |
| US20160369313A1 (en) | 2016-12-22 |
| MX348325B (es) | 2017-06-06 |
| JP2013530719A (ja) | 2013-08-01 |
| AR082261A1 (es) | 2012-11-21 |
| KR20130041953A (ko) | 2013-04-25 |
| BR112013001109A2 (pt) | 2016-05-24 |
| CN103080329A (zh) | 2013-05-01 |
| EP2596113A1 (en) | 2013-05-29 |
| CN103080329B (zh) | 2016-08-03 |
| AU2011281663A1 (en) | 2013-03-07 |
| DK2596113T3 (en) | 2019-01-07 |
| EP2596113B1 (en) | 2018-09-12 |
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