CA2992497C - Procede de production de galacto-oligosaccharides a partir de lactose - Google Patents
Procede de production de galacto-oligosaccharides a partir de lactose Download PDFInfo
- Publication number
- CA2992497C CA2992497C CA2992497A CA2992497A CA2992497C CA 2992497 C CA2992497 C CA 2992497C CA 2992497 A CA2992497 A CA 2992497A CA 2992497 A CA2992497 A CA 2992497A CA 2992497 C CA2992497 C CA 2992497C
- Authority
- CA
- Canada
- Prior art keywords
- aqueous solution
- initial
- lactose
- acid
- adjusting
- 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.)
- Active
Links
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 title claims abstract description 239
- 239000008101 lactose Substances 0.000 title claims abstract description 239
- 235000021255 galacto-oligosaccharides Nutrition 0.000 title claims abstract description 148
- 150000003271 galactooligosaccharides Chemical class 0.000 title claims abstract description 145
- 238000004519 manufacturing process Methods 0.000 title description 3
- 108010005774 beta-Galactosidase Proteins 0.000 claims abstract description 208
- 108010059881 Lactase Proteins 0.000 claims abstract description 204
- 102100026189 Beta-galactosidase Human genes 0.000 claims abstract description 199
- 229940116108 lactase Drugs 0.000 claims abstract description 199
- 238000000034 method Methods 0.000 claims abstract description 174
- 230000007935 neutral effect Effects 0.000 claims abstract description 110
- 238000011534 incubation Methods 0.000 claims abstract description 20
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 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 claims abstract description 8
- 239000007864 aqueous solution Substances 0.000 claims description 450
- 239000002253 acid Substances 0.000 claims description 119
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 114
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 76
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 75
- 239000000203 mixture Substances 0.000 claims description 70
- 235000000346 sugar Nutrition 0.000 claims description 58
- 235000020357 syrup Nutrition 0.000 claims description 48
- 239000006188 syrup Substances 0.000 claims description 48
- 239000000243 solution Substances 0.000 claims description 47
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 38
- 150000001720 carbohydrates Chemical class 0.000 claims description 33
- 235000014633 carbohydrates Nutrition 0.000 claims description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 31
- 241001138401 Kluyveromyces lactis Species 0.000 claims description 28
- 240000006439 Aspergillus oryzae Species 0.000 claims description 27
- 235000002247 Aspergillus oryzae Nutrition 0.000 claims description 27
- 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 claims description 22
- 229930182830 galactose Natural products 0.000 claims description 22
- 239000008103 glucose Substances 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 12
- 238000013375 chromatographic separation Methods 0.000 claims description 9
- 238000005342 ion exchange Methods 0.000 claims description 9
- 241000228212 Aspergillus Species 0.000 claims description 8
- 241000235649 Kluyveromyces Species 0.000 claims description 8
- 238000004587 chromatography analysis Methods 0.000 claims description 7
- 238000000855 fermentation Methods 0.000 claims description 5
- 230000004151 fermentation Effects 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 abstract description 57
- 230000029087 digestion Effects 0.000 abstract description 8
- 230000002255 enzymatic effect Effects 0.000 abstract description 2
- 230000000813 microbial effect Effects 0.000 abstract description 2
- 230000002538 fungal effect Effects 0.000 description 67
- 108090000790 Enzymes Proteins 0.000 description 26
- 102000004190 Enzymes Human genes 0.000 description 26
- 229940088598 enzyme Drugs 0.000 description 26
- 238000013019 agitation Methods 0.000 description 12
- 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 11
- 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 10
- 239000012141 concentrate Substances 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 235000008504 concentrate Nutrition 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 150000008163 sugars Chemical class 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 229960002337 magnesium chloride Drugs 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 102000005936 beta-Galactosidase Human genes 0.000 description 4
- -1 disaccharide GOS Chemical class 0.000 description 4
- 229940050906 magnesium chloride hexahydrate Drugs 0.000 description 4
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 4
- 235000013336 milk Nutrition 0.000 description 4
- 239000008267 milk Substances 0.000 description 4
- 210000004080 milk Anatomy 0.000 description 4
- 239000012466 permeate Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 125000002519 galactosyl group Chemical group C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229920001542 oligosaccharide Polymers 0.000 description 3
- 150000002482 oligosaccharides Chemical class 0.000 description 3
- 238000010979 pH adjustment Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 238000004255 ion exchange chromatography Methods 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 201000010538 Lactose Intolerance Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 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 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 230000006862 enzymatic digestion Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000008195 galaktosides Chemical class 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 150000002402 hexoses Chemical group 0.000 description 1
- 235000020256 human milk Nutrition 0.000 description 1
- 210000004251 human milk Anatomy 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229940091250 magnesium supplement Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000021140 nondigestible carbohydrates Nutrition 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000006041 probiotic Substances 0.000 description 1
- 230000000529 probiotic effect Effects 0.000 description 1
- 235000018291 probiotics Nutrition 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Classifications
-
- 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
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0036—Galactans; Derivatives thereof
-
- 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)
- C12N9/2405—Glucanases
- C12N9/2434—Glucanases acting on beta-1,4-glucosidic bonds
- C12N9/2445—Beta-glucosidase (3.2.1.21)
-
- 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
- C12P19/14—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)
- C12Y302/01021—Beta-glucosidase (3.2.1.21)
-
- 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)
- C12Y302/01108—Lactase (3.2.1.108)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Microbiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Dairy Products (AREA)
- Enzymes And Modification Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
L'invention concerne des procédés de préparation enzymatique de galacto-oligosaccharides (GOS) à partir de lactose en utilisant deux différentes enzymes de lactase microbienne afin de maximiser l'étendue degré de transgalactosylation pendant la digestion du lactose. L'invention concerne également des procédés permettant d'éviter la turbidité d'une solution comprenant des GOS et du lactose à mesure qu'elle est est ajustée pour incubation avec une lactase neutre de levure.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662277838P | 2016-01-12 | 2016-01-12 | |
| US62/277,838 | 2016-01-12 | ||
| PCT/CA2017/050042 WO2017120678A1 (fr) | 2016-01-12 | 2017-01-12 | Procédé de production de galacto-oligosaccharides à partir de lactose |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2992497A1 CA2992497A1 (fr) | 2017-07-20 |
| CA2992497C true CA2992497C (fr) | 2020-12-22 |
Family
ID=59310498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2992497A Active CA2992497C (fr) | 2016-01-12 | 2017-01-12 | Procede de production de galacto-oligosaccharides a partir de lactose |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP3402892A1 (fr) |
| CN (1) | CN108138208A (fr) |
| AU (1) | AU2017207540A1 (fr) |
| CA (1) | CA2992497C (fr) |
| WO (1) | WO2017120678A1 (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20210010045A1 (en) * | 2017-07-04 | 2021-01-14 | Kabushiki Kaisha Yakult Honsha | Method for producing galactooligosaccharide |
| WO2023161321A1 (fr) | 2022-02-25 | 2023-08-31 | Frieslandcampina Nederland B.V. | Procédé de préparation de galacto-oligosaccharide de haute pureté |
| GB2616483A (en) * | 2022-03-11 | 2023-09-13 | Clasado Res Services Limited | Oligosaccharide composition |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4095816B2 (ja) * | 2002-03-20 | 2008-06-04 | 日本オリゴ株式会社 | ガラクトオリゴ糖の製造法 |
| AU2010223965A1 (en) * | 2009-03-13 | 2011-10-06 | Dsm Food Specialties Usa Inc. | Prebiotic oligosaccharides |
| US20110189342A1 (en) * | 2010-02-01 | 2011-08-04 | Jeong Hea-Seok | High-purity galactooligosaccharides and uses thereof |
| CN101831389B (zh) * | 2010-04-19 | 2011-12-07 | 江南大学 | 一种产β-D-半乳糖苷酶的菌株及用该酶生产低聚半乳糖的方法 |
| TWI527522B (zh) * | 2010-08-13 | 2016-04-01 | 愛之味股份有限公司 | 製備富含半乳寡醣及低乳糖之易吸收乳製品之方法及以該方法製備之機能性乳製品 |
| CN102369998A (zh) * | 2010-08-13 | 2012-03-14 | 爱之味股份有限公司 | 制备富含低聚半乳糖和低乳糖的易吸收乳制品的方法 |
| EP2620506A1 (fr) * | 2012-01-25 | 2013-07-31 | Arla Foods Amba | Procédé de production de composition contenant des galacto-oligosaccharides |
| CN104812908A (zh) * | 2013-07-23 | 2015-07-29 | 新克莱玛有限公司 | 强化作为母乳成分的半乳糖乳糖的低聚半乳糖的制备方法 |
| CN103993054B (zh) * | 2014-05-19 | 2016-05-25 | 山东龙力生物科技股份有限公司 | 一种酶协同制备高纯度低聚半乳糖的方法 |
| CN104805026A (zh) * | 2015-04-21 | 2015-07-29 | 山东福瑞达生物科技有限公司 | 一株产β-半乳糖苷酶菌株及其制备高纯度低聚半乳糖的方法 |
| CN104975056B (zh) | 2015-07-21 | 2018-11-16 | 保龄宝生物股份有限公司 | 一种高含量低聚半乳糖的生产方法 |
| CN105274165A (zh) * | 2015-11-20 | 2016-01-27 | 保龄宝生物股份有限公司 | 一种高含量低聚半乳糖的简便生产方法 |
| CN105274164A (zh) * | 2015-11-20 | 2016-01-27 | 保龄宝生物股份有限公司 | 一种低聚半乳糖的制备方法 |
-
2017
- 2017-01-12 EP EP17738066.4A patent/EP3402892A1/fr not_active Withdrawn
- 2017-01-12 WO PCT/CA2017/050042 patent/WO2017120678A1/fr active Application Filing
- 2017-01-12 AU AU2017207540A patent/AU2017207540A1/en not_active Abandoned
- 2017-01-12 CN CN201780003136.XA patent/CN108138208A/zh active Pending
- 2017-01-12 CA CA2992497A patent/CA2992497C/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| AU2017207540A1 (en) | 2018-04-12 |
| CA2992497A1 (fr) | 2017-07-20 |
| EP3402892A4 (fr) | 2018-11-21 |
| EP3402892A1 (fr) | 2018-11-21 |
| CN108138208A (zh) | 2018-06-08 |
| WO2017120678A1 (fr) | 2017-07-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20180115 |