JP6796489B2 - 調製方法 - Google Patents
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- JP6796489B2 JP6796489B2 JP2016540836A JP2016540836A JP6796489B2 JP 6796489 B2 JP6796489 B2 JP 6796489B2 JP 2016540836 A JP2016540836 A JP 2016540836A JP 2016540836 A JP2016540836 A JP 2016540836A JP 6796489 B2 JP6796489 B2 JP 6796489B2
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- 238000002360 preparation method Methods 0.000 title claims description 32
- 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 claims description 151
- 239000008101 lactose Substances 0.000 claims description 151
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- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 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 5
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- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 2
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
- 244000269722 Thea sinensis Species 0.000 description 2
- 108010046377 Whey Proteins Proteins 0.000 description 2
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- 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 2
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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 2
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- 108010072642 galactosyl receptor Proteins 0.000 description 2
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- 229930195724 β-lactose Natural products 0.000 description 2
- 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 1
- 241000228245 Aspergillus niger Species 0.000 description 1
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- 241000283690 Bos taurus Species 0.000 description 1
- 102000011632 Caseins Human genes 0.000 description 1
- 108010076119 Caseins Proteins 0.000 description 1
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 102000002464 Galactosidases Human genes 0.000 description 1
- 108010093031 Galactosidases Proteins 0.000 description 1
- 241000410156 Mesocnemis singularis Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000005862 Whey Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000004520 agglutination Effects 0.000 description 1
- DLRVVLDZNNYCBX-CAPXFGMSSA-N allolactose Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)O1 DLRVVLDZNNYCBX-CAPXFGMSSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000011942 biocatalyst Substances 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 1
- 239000001354 calcium citrate Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- AIUDWMLXCFRVDR-UHFFFAOYSA-N dimethyl 2-(3-ethyl-3-methylpentyl)propanedioate Chemical class CCC(C)(CC)CCC(C(=O)OC)C(=O)OC AIUDWMLXCFRVDR-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 244000005709 gut microbiome Species 0.000 description 1
- 235000020256 human milk Nutrition 0.000 description 1
- 210000004251 human milk Anatomy 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 229940066779 peptones Drugs 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 238000004375 physisorption Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000019192 riboflavin Nutrition 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 235000021119 whey protein Nutrition 0.000 description 1
- 235000021247 β-casein Nutrition 0.000 description 1
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- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
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- 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
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- 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
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- 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)
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Description
ラクトースの溶解度=0.003*T^2+0.2713*T+9.778
下記の実例は、固定化β−ガラクトシダーゼを用いるGOSの製造において高濃縮ラクトース溶液の代わりにラクトーススラリを用いる利点を例示している。
35グラムのラクトースを25グラムの0.1M K2HPO4/KH2PO4バッファ、pH6.3、に添加し、95℃において完全に溶解させ、次いで58℃に冷却した。その後、市販の担体(セパビーズEC−HA)上にグルタルアルデヒドカップリングにより固定化された担体結合酵素、特異的活性(specific activity)131.16LU/グラム固定化酵素、2.7グラムを添加して酵素反応を初期設定した。酵素の用量は、10.2LU/グラム・ラクトースである。
85グラムのラクトースを65グラムの0.1M K2HPO4/KH2PO4バッファ、pH6に直接添加し、次いで反応混合物を反応温度58℃に加熱し(および少なくとも1時間維持し)、そして2mlの脱塩水に溶解された85mgのBiolacta N5(Amano)の遊離β−ガラクトシダーゼを添加して、反応を初期設定した。酵素用量は、5LU/グラム・ラクトースである。
1. Rivero-Urgell M and Santamaria-Orleans A (2001) Oligosaccharides: application in infant food. Early Human Development 65 Suppl. S43-S52
2. Torres D, Goncalves M, Teixeira J, Rodrigues L: Galacto-oligosaccharides: production, properties, applications, and significance as prebiotics. Compr Rev Food Sci, Food Safety 2010, 9:438-454.
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Claims (14)
- ラクトースからガラクト−オリゴサッカライド(GOS)を調製する調製方法であって、
(i)ラクトース結晶を室温の液相に溶解し、少なくとも53%(重量/重量)のラクトースを含有する結晶化されたラクトースの水系スラリを用意することと、
(ii)結晶化されたラクトースの前記水系スラリを、室温から所望の反応温度である20℃−60℃まで加熱することと、
(iii)前記加熱された、結晶化されたラクトースの水系スラリを、固定化されたβ−ガラクトシダーゼ(EC 3.2.1.23)と接触させることと、
(iv)GOS合成を行わせることを含み、
前記β−ガラクトシダーゼは、多孔質担体に固定化されたB.circulans β−ガラクトシダーゼである調製方法。 - 請求項1に記載の調製方法において、
前記水系ラクトーススラリは、少なくとも55%(重量/重量)のラクトースを含有する調製方法。 - 請求項2に記載の調製方法において、
前記水系ラクトーススラリは、55%〜70%(重量/重量)のラクトースを含有する調製方法。 - 請求項1から3までのいずれか一項に記載の調製方法において、
前記水系ラクトーススラリは食品等級または医薬品等級のラクトースを含有する調製方法。 - 請求項1から4までのいずれか一項に記載の調製方法において、
前記水系ラクトーススラリのpHはpH6.0〜7.5である調製方法。 - 請求項1から5までのいずれか一項に記載の調製方法において、
前記GOS合成は、40℃と60℃の間の反応温度において行われる調製方法。 - 請求項1から6までのいずれか一項に記載の調製方法において、
前記GOS合成は、少なくとも6時間の反応期間の間行われる調製方法。 - 請求項1から7までのいずれか一項に記載の調製方法において、
前記固定化されたβ−ガラクトシダーゼは30LU/グラム・当初ラクトース以下の量で用いる調製方法。 - 請求項8に記載の調製方法において、
前記固定化されたβ−ガラクトシダーゼは10LU/グラムと20LU/グラム・当初ラクトースの間の量で用いる調製方法。 - 請求項1に記載の調製方法において、
前記多孔質担体は活性化アクリルポリマー担体である調製方法。 - 請求項10に記載の調製方法において、
前記多孔質担体は機能化ポリメタクリレートマトリックスである調製方法。 - 請求項11に記載の調製方法において、
前記多孔質担体はヘキサメチレンアミノ−機能化ポリメタクリレートマトリックスまたはマクロ多孔質アクリルエポキシ−活性化樹脂である調製方法。 - 請求項1から12までのいずれか一項に記載の調製方法において、
さらに、前記GOS合成の第1サイクルに引き続き、
(a)前記固定化されたβ−ガラクトシダーゼを水および/またはバッファを用いて洗浄する工程、
(b)任意に前記洗浄された固定化β−ガラクトシダーゼをさらなる使用まで貯蔵する工程、
(c)GOS合成の少なくとも1つの後続サイクルを、工程(a)の前記洗浄された固定化β−ガラクトシダーゼをラクトーススラリに、前記固定化された酵素が再使用されるように、接触させることにより行う工程を含む調製方法。 - 請求項13に記載の調製方法において、
再使用された固定化β−ガラクトシダーゼを用いて、少なくとも5サイクルのGOS合成を行う調製方法。
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