JPS60251896A - ガラクトオリゴ糖の製造方法 - Google Patents
ガラクトオリゴ糖の製造方法Info
- Publication number
- JPS60251896A JPS60251896A JP59108547A JP10854784A JPS60251896A JP S60251896 A JPS60251896 A JP S60251896A JP 59108547 A JP59108547 A JP 59108547A JP 10854784 A JP10854784 A JP 10854784A JP S60251896 A JPS60251896 A JP S60251896A
- Authority
- JP
- Japan
- Prior art keywords
- galactooligosaccharide
- galactopyranosyl
- culture
- producing
- glucose
- 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.)
- Granted
Links
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- 235000021255 galacto-oligosaccharides Nutrition 0.000 title claims abstract description 49
- 241001337994 Cryptococcus <scale insect> Species 0.000 claims abstract description 9
- 241000222051 Papiliotrema laurentii Species 0.000 claims abstract 2
- 244000005700 microbiome Species 0.000 claims description 20
- 235000000346 sugar Nutrition 0.000 claims description 18
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- 238000004519 manufacturing process Methods 0.000 claims description 16
- 239000008103 glucose Substances 0.000 claims description 14
- 238000012258 culturing Methods 0.000 claims description 5
- 125000003132 pyranosyl group Chemical group 0.000 claims 1
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- 239000008101 lactose Substances 0.000 abstract description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 21
- 239000000706 filtrate Substances 0.000 abstract description 7
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- RXVWSYJTUUKTEA-DSOVBJLESA-N (2r,3r,4r,5r)-4-[(2s,3r,4r,5r,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal Chemical compound O[C@@H]1[C@@H](O)[C@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)O[C@H](CO)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 RXVWSYJTUUKTEA-DSOVBJLESA-N 0.000 abstract 1
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- 239000002609 medium Substances 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- 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 14
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920001202 Inulin Polymers 0.000 description 2
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 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 2
- 238000004458 analytical method Methods 0.000 description 2
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- YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 description 2
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- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 230000034303 cell budding Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- KSCFJBIXMNOVSH-UHFFFAOYSA-N dyphylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1N(CC(O)CO)C=N2 KSCFJBIXMNOVSH-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000002538 fungal effect 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
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 229940116871 l-lactate Drugs 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- QWIZNVHXZXRPDR-WSCXOGSTSA-N melezitose Chemical compound O([C@@]1(O[C@@H]([C@H]([C@@H]1O[C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O)CO)CO)[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O QWIZNVHXZXRPDR-WSCXOGSTSA-N 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- HOVAGTYPODGVJG-ZFYZTMLRSA-N methyl alpha-D-glucopyranoside Chemical compound CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HOVAGTYPODGVJG-ZFYZTMLRSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- BJRNKVDFDLYUGJ-UHFFFAOYSA-N p-hydroxyphenyl beta-D-alloside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-UHFFFAOYSA-N 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose 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[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- NGFMICBWJRZIBI-UJPOAAIJSA-N salicin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC=C1CO NGFMICBWJRZIBI-UJPOAAIJSA-N 0.000 description 1
- 229940120668 salicin Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007362 sporulation medium Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229910021654 trace metal Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000009777 vacuum freeze-drying Methods 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59108547A JPS60251896A (ja) | 1984-05-30 | 1984-05-30 | ガラクトオリゴ糖の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59108547A JPS60251896A (ja) | 1984-05-30 | 1984-05-30 | ガラクトオリゴ糖の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60251896A true JPS60251896A (ja) | 1985-12-12 |
| JPH029796B2 JPH029796B2 (enrdf_load_stackoverflow) | 1990-03-05 |
Family
ID=14487593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59108547A Granted JPS60251896A (ja) | 1984-05-30 | 1984-05-30 | ガラクトオリゴ糖の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60251896A (enrdf_load_stackoverflow) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6384486A (ja) * | 1986-09-27 | 1988-04-15 | Unitika Ltd | ビフイドバクテリウム菌の増殖促進剤の製造法 |
| JPS63185373A (ja) * | 1986-09-27 | 1988-07-30 | Unitika Ltd | ビフイドバクテリウム菌の増殖促進剤の製造法 |
| JPS63196240A (ja) * | 1987-02-12 | 1988-08-15 | Nisshin Seito Kk | 複合甘味料 |
| JPS6486857A (en) * | 1987-09-30 | 1989-03-31 | Nisshin Seito Kk | Low cariogenic food and beverage |
| AU603165B2 (en) * | 1986-12-15 | 1990-11-08 | Kabushiki Kaisha Yakult Honsha | Method for producing galactooligosaccharide |
| WO1992000310A1 (fr) * | 1990-06-27 | 1992-01-09 | Dainippon Ink & Chemicals, Inc. | Oligosaccharide alkyle et derive acetyle de celui-ci |
| US5578584A (en) * | 1993-03-24 | 1996-11-26 | Matsutani Chemical Industry Co., Ltd. | Feed containing galacto-oligosaccharides for domestic fowls |
| WO2015166903A1 (ja) * | 2014-05-02 | 2015-11-05 | 株式会社ヤクルト本社 | ４'－ｇｌ高純度組成物の調製法 |
| WO2017115826A1 (ja) * | 2015-12-29 | 2017-07-06 | 天野エンザイム株式会社 | 新規β－ガラクトシダーゼ |
-
1984
- 1984-05-30 JP JP59108547A patent/JPS60251896A/ja active Granted
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6384486A (ja) * | 1986-09-27 | 1988-04-15 | Unitika Ltd | ビフイドバクテリウム菌の増殖促進剤の製造法 |
| JPS63185373A (ja) * | 1986-09-27 | 1988-07-30 | Unitika Ltd | ビフイドバクテリウム菌の増殖促進剤の製造法 |
| US5294546A (en) * | 1986-09-27 | 1994-03-15 | Unitika Ltd. | Method for production of a growth factor for Bifidobacterium sp. |
| AU603165B2 (en) * | 1986-12-15 | 1990-11-08 | Kabushiki Kaisha Yakult Honsha | Method for producing galactooligosaccharide |
| JPS63196240A (ja) * | 1987-02-12 | 1988-08-15 | Nisshin Seito Kk | 複合甘味料 |
| JPS6486857A (en) * | 1987-09-30 | 1989-03-31 | Nisshin Seito Kk | Low cariogenic food and beverage |
| WO1992000310A1 (fr) * | 1990-06-27 | 1992-01-09 | Dainippon Ink & Chemicals, Inc. | Oligosaccharide alkyle et derive acetyle de celui-ci |
| US5268461A (en) * | 1990-06-27 | 1993-12-07 | Dainippon Ink & Chemicals, Inc. | Alkylated oligosaccharides and acetyl derivatives of the same |
| US5578584A (en) * | 1993-03-24 | 1996-11-26 | Matsutani Chemical Industry Co., Ltd. | Feed containing galacto-oligosaccharides for domestic fowls |
| KR20160146790A (ko) * | 2014-05-02 | 2016-12-21 | 가부시키가이샤 야쿠르트 혼샤 | 4''-gl 고순도 조성물의 조제법 |
| WO2015166903A1 (ja) * | 2014-05-02 | 2015-11-05 | 株式会社ヤクルト本社 | ４'－ｇｌ高純度組成物の調製法 |
| US20170044200A1 (en) * | 2014-05-02 | 2017-02-16 | Kabushiki Kaisha Yakult Honsha | Preparation method for high-purity 4'-galactosyl-lactose composition |
| CN106459117A (zh) * | 2014-05-02 | 2017-02-22 | 株式会社益力多本社 | 4’‑gl高纯度组合物的制备方法 |
| EP3138848A4 (en) * | 2014-05-02 | 2017-03-08 | Kabushiki Kaisha Yakult Honsha | Preparation method for high-purity 4'-galactosyl-lactose composition |
| JPWO2015166903A1 (ja) * | 2014-05-02 | 2017-04-20 | 株式会社ヤクルト本社 | ４’−ｇｌ高純度組成物の調製法 |
| US10221204B2 (en) | 2014-05-02 | 2019-03-05 | Kabushiki Kaisha Yakult Honsha | Preparation method for high-purity 4′-galactosyl-lactose composition |
| TWI659107B (zh) * | 2014-05-02 | 2019-05-11 | 日商養樂多本社股份有限公司 | ４’－ｇｌ高純度組成物之調製法 |
| WO2017115826A1 (ja) * | 2015-12-29 | 2017-07-06 | 天野エンザイム株式会社 | 新規β－ガラクトシダーゼ |
| JPWO2017115826A1 (ja) * | 2015-12-29 | 2018-10-18 | 天野エンザイム株式会社 | 新規β−ガラクトシダーゼ |
| US11512299B2 (en) | 2015-12-29 | 2022-11-29 | Amano Enzyme Inc. | Beta-galactosidase enzymes |
| US11859222B2 (en) | 2015-12-29 | 2024-01-02 | Amano Enzyme Inc. | Beta-galactosidase enzymes |
| US12371684B2 (en) | 2015-12-29 | 2025-07-29 | Amano Enzyme Inc. | Beta-galactosidase enzymes |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH029796B2 (enrdf_load_stackoverflow) | 1990-03-05 |
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