JPH0631286B2 - Method for producing sialic acid-containing composition - Google Patents
Method for producing sialic acid-containing compositionInfo
- Publication number
- JPH0631286B2 JPH0631286B2 JP62325500A JP32550087A JPH0631286B2 JP H0631286 B2 JPH0631286 B2 JP H0631286B2 JP 62325500 A JP62325500 A JP 62325500A JP 32550087 A JP32550087 A JP 32550087A JP H0631286 B2 JPH0631286 B2 JP H0631286B2
- Authority
- JP
- Japan
- Prior art keywords
- ultrafiltration
- sialic acid
- sialic
- milk
- containing composition
- 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.)
- Expired - Fee Related
Links
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 title claims description 24
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 title claims description 23
- 239000000203 mixture Substances 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000000108 ultra-filtration Methods 0.000 claims description 40
- 125000005629 sialic acid group Chemical group 0.000 claims description 25
- 239000012466 permeate Substances 0.000 claims description 10
- 239000002994 raw material Substances 0.000 claims description 10
- 235000013365 dairy product Nutrition 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 235000013336 milk Nutrition 0.000 description 12
- 239000008267 milk Substances 0.000 description 12
- 210000004080 milk Anatomy 0.000 description 12
- 108010046377 Whey Proteins Proteins 0.000 description 11
- 102000007544 Whey Proteins Human genes 0.000 description 11
- 239000005862 Whey Substances 0.000 description 10
- 108010076119 Caseins Proteins 0.000 description 9
- 102000011632 Caseins Human genes 0.000 description 9
- 239000012528 membrane Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 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 description 8
- 239000005018 casein Substances 0.000 description 8
- 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 8
- 235000021240 caseins Nutrition 0.000 description 8
- 239000008101 lactose Substances 0.000 description 8
- 102000004169 proteins and genes Human genes 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 229920001542 oligosaccharide Polymers 0.000 description 6
- 150000002482 oligosaccharides Chemical class 0.000 description 6
- 235000018102 proteins Nutrition 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 102000003886 Glycoproteins Human genes 0.000 description 4
- 108090000288 Glycoproteins Proteins 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 235000020183 skimmed milk Nutrition 0.000 description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- 108010067454 caseinomacropeptide Proteins 0.000 description 3
- 238000011026 diafiltration Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229930186217 Glycolipid Natural products 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 235000015155 buttermilk Nutrition 0.000 description 2
- 235000013351 cheese Nutrition 0.000 description 2
- 235000020247 cow milk Nutrition 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 108010058314 rennet Proteins 0.000 description 2
- 229940108461 rennet Drugs 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- OIZGSVFYNBZVIK-FHHHURIISA-N 3'-sialyllactose Chemical compound O1[C@@H]([C@H](O)[C@H](O)CO)[C@H](NC(=O)C)[C@@H](O)C[C@@]1(C(O)=O)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 OIZGSVFYNBZVIK-FHHHURIISA-N 0.000 description 1
- 206010065042 Immune reconstitution inflammatory syndrome Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000909 electrodialysis Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013350 formula milk Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 235000020256 human milk Nutrition 0.000 description 1
- 210000004251 human milk Anatomy 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003014 ion exchange membrane Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 235000021119 whey protein Nutrition 0.000 description 1
- 235000021246 κ-casein Nutrition 0.000 description 1
Landscapes
- Dairy Products (AREA)
- Saccharide Compounds (AREA)
- Peptides Or Proteins (AREA)
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は、本来牛乳に含有されているシアル酸類を種々
の乳質原料物質から分別し調製する方法に関するもので
ある。TECHNICAL FIELD The present invention relates to a method for separating and preparing sialic acids originally contained in milk from various dairy raw materials.
（従来の技術とその問題点） 牛乳中に存在するシアル酸類としては、大きく分けてシ
アリルラクトースに代表されるシアル酸結合オリゴ糖、
タンパク質にシアル酸が結合した糖タンパク質、脂質に
結合した糖脂質があることが従来より知られていた。特
に近年、糖タンパク質や糖脂質のような複合糖質中の糖
鎖が、生体における細胞間識別に重要な働きを果たすこ
とが認められている。シアル酸は、この細胞間識別を行
うレセプターの必要構成成分である。また、母乳中には
牛乳に比べ約３〜５倍程度のシアル酸類が含まれてお
り、これらシアル酸類も乳児の感染防御因子の一つとし
て働いていると考えられている。(Prior art and its problems) Sialic acids present in milk are roughly classified into sialic acid-bound oligosaccharides represented by sialyllactose,
It has been conventionally known that there are glycoproteins in which sialic acid is bound to proteins and glycolipids in which lipids are bound. Particularly in recent years, it has been recognized that sugar chains in glycoconjugates such as glycoproteins and glycolipids play an important role in cell-to-cell discrimination in the living body. Sialic acid is a necessary component of the receptor that performs this cell-cell discrimination. Further, breast milk contains about 3 to 5 times as much sialic acids as cow's milk, and these sialic acids are also considered to act as one of infants' infection defense factors.
すでに、牛乳中のシアル酸類を分別する技術としては特
公昭40−21234号があり、該公報では牛乳より分離した
カゼインを出発原料として、これを苛性ソーダのような
アルカリで溶解し、このカゼイン溶液に塩化カルシウム
を加え、糖含量の高い上澄みを得、更に、この上澄みを
イオン交換膜等を用いミネラル分を除去し、目的の糖タ
ンパク含有の高い画分を得るというものである。この方
法は、カゼインのシアル酸類を含む高糖タンパク画分を
得るというもので、本来牛乳中に含まれているシアル酸
類の一部を調製したにすぎない。工業的な大量調製を考
えた場合、操作が煩雑であり、なおかつ、食用に供する
ためには、塩化カルシウムおよびカゼイン溶解に使用し
た苛性ソーダ等のアルカリを十分に除去する必要があ
る。また、高糖タンパク画分を得た残りのカゼインの使
用や処理にも塩化カルシウムや苛性ソーダが含有してい
るため問題が残る。Already, as a technique for separating sialic acids in milk, there is JP-B-40-21234, and in this publication, casein separated from milk is used as a starting material, and this is dissolved in an alkali such as caustic soda to give this casein solution. Calcium chloride is added to obtain a supernatant having a high sugar content, and the supernatant is subjected to removal of minerals using an ion exchange membrane or the like to obtain a target fraction having a high glycoprotein content. This method is to obtain a high glycoprotein fraction containing sialic acids of casein, and only prepares a part of the sialic acids originally contained in milk. Considering industrial large-scale preparation, the operation is complicated, and it is necessary to sufficiently remove the alkali such as caustic soda used for dissolving calcium chloride and casein in order to use it for food. Further, the use and treatment of the remaining casein from which the high-glycoprotein fraction has been obtained also poses a problem because it contains calcium chloride and caustic soda.
牛乳中のシアル酸類を調製する別の方法として特開昭59
−184197号にシアル酸結合オリゴ糖の調製法がある。こ
の方法は、牛乳中に含まれているシアル酸結合オリゴ糖
の調製法であり、他のシアル酸類、例えばκ−カゼイン
にレンネットを作用させて生成するＧＭＰ（グリコマク
ロペプチド）等の高シアル酸含有ペプチドの分離回収は
出来ない。また、シアル酸結合オリゴ糖をアニオン樹脂
に吸着させるために十分な電気透析を実施しなければな
らず、工業的生産に際し、多額の設備投費や、また高い
運転コストを要し、経済的に問題がある。As another method for preparing sialic acids in milk
-184197 describes a method for preparing sialic acid-linked oligosaccharides. This method is a method for preparing a sialic acid-binding oligosaccharide contained in milk, and has a high sialic acid such as GMP (glyco-macropeptide) produced by allowing rennet to act on other sialic acids such as κ-casein. The acid-containing peptide cannot be separated and collected. In addition, sufficient electrodialysis must be carried out to adsorb the sialic acid-bound oligosaccharide to the anion resin, which requires a large amount of equipment investment and high operating cost for industrial production, which is economical. There's a problem.
本発明は、乳質原料物質中のシアル酸類を膜分離技術を
用い工業的規模で効率よく製造する方法を提案すること
を課題とする。An object of the present invention is to propose a method for efficiently producing sialic acids in a milk raw material on an industrial scale by using a membrane separation technique.
（問題点を解決するための手段） 本発明は、シアル酸類を含有する乳質原料物質をpH4.0
〜6.0に調整して20,000〜500,000ダルトンの分画分子量
を有する限外濾過装置を用い一次限外濾過を実施し、そ
の限外濾過透過液を更にpH6.0〜8.0に調整して1,000〜1
0,000ダルトンの分画分子量を有する限外濾過装置を用
いて二次限外濾過を行い、低分子物質を除去することを
特徴とする。(Means for Solving Problems) The present invention provides a dairy raw material containing sialic acids with a pH value of 4.0
The first ultrafiltration is performed by using an ultrafiltration device having a molecular weight cut-off of 20,000 to 500,000 daltons adjusted to ~ 6.0, and the ultrafiltration permeate is further adjusted to pH 6.0 to 8.0 to 1,000 ~ 1
Secondary ultrafiltration is performed by using an ultrafiltration device having a cut-off molecular weight of 0,000 daltons to remove low-molecular substances.
ここで言う乳質原料物質とは、牛乳、脱脂乳、バターミ
ルクならびにホエーなどを意味する。The dairy raw material here means cow milk, skim milk, buttermilk, whey, and the like.
本発明の出発原材料は、シアル酸類を含有する牛乳、脱
脂乳、バターミルク等のほかにホエーを用いることがで
きる。また、ホエーもチーズ製造時に生成されるホエー
のみならず、酸カゼインやレンネットカゼインを製造す
る時に生成されることらのホエーであってもよい。さら
にホエーおよびパーミェートより乳糖を製造する時に生
成されるマザリカ（乳糖母液）を用いてもよい。更に、
乳およびホエーを加熱変成させ、タンパクを沈澱させて
得られる上澄みを用いることができる。As the starting raw material of the present invention, whey can be used in addition to milk, skim milk, buttermilk containing sialic acids. Further, whey is not limited to whey produced during cheese production, but may be whey produced during production of acid casein or rennet casein. Furthermore, mazarica (lactose mother liquor) produced when producing lactose from whey and permeate may be used. Furthermore,
The supernatant obtained by heat denaturing milk and whey to precipitate proteins can be used.
これら出発原材料を一次限外濾過を行う前に、膜透過性
の増加および回収率の向上のために、乳酸、クエン酸等
の有機酸および塩酸、硫酸等の無機酸によりpH4.0〜6.0
に調整することが好ましい。これにより、イオン強度が
上がり、シアル酸類の解離がよくなり、膜透過性が良く
なる。その理由はシアル酸類のpHが中性域にある時は会
合しポリマーとなって高分子化し、酸性域では解離して
低分子化するからである。Before carrying out primary ultrafiltration on these starting raw materials, in order to increase membrane permeability and improve recovery rate, organic acids such as lactic acid and citric acid, and inorganic acids such as hydrochloric acid and sulfuric acid are used to adjust the pH to 4.0 to 6.0.
It is preferable to adjust This increases ionic strength, improves dissociation of sialic acids, and improves membrane permeability. The reason is that when the pH of the sialic acid is in the neutral range, it associates to form a polymer and becomes a polymer, and in the acidic range it dissociates and becomes a low molecular weight.
これら出発原材料をまず、20,000〜500,000ダルトンの
分画分子量を有する限外濾過装置を用いて一次限外濾過
を行う。このとき、500,000ダルトンを超えると、一部
タンパクが透過し、目的のシアル酸類とタンパクを含む
高分子との分離が出来難くなる。また、20,000ダルトン
より細かいと、シアル酸類の一次限外濾過液への移行が
少なくなり、回収率が大きく影響される。These starting raw materials are first subjected to primary ultrafiltration using an ultrafiltration device having a molecular weight cut off of 20,000 to 500,000 daltons. At this time, when the amount exceeds 500,000 daltons, some proteins permeate and it becomes difficult to separate the desired sialic acids from the polymer containing the protein. If it is finer than 20,000 daltons, the transfer of sialic acids to the primary ultrafiltrate is reduced and the recovery rate is greatly affected.
この限外濾過により乳糖、ミネラルおよびペプチドを含
む非タンパク態窒素等が、この一次限外濾過透過液中に
含まれる。この時の限外濾過装置の運転圧力は、その時
使用する限外濾過膜に応じ0.2〜1.0MPaで運転する。ま
た、この時、限外濾過装置内で濃縮される液中には脂肪
およびタンパク質が含まれている。例えば、ホエーを出
発原料として使用した場合、これらのタンパク濃縮物
は、ホエータンパク濃縮物と呼ばれ、現在食用として広
く利用されている。一方、この一次限外濾過透過液は、
濃縮し、乳糖を回収するのに用いられるか、また廃棄さ
れるかで、利用方法は限られている。これら乳質原材料
の一次限外濾過透過液中には、３〜10mg％のシアル酸類
が含まれている。By this ultrafiltration, non-protein nitrogen containing lactose, minerals and peptides is contained in this primary ultrafiltration permeate. The operating pressure of the ultrafiltration device at this time is 0.2 to 1.0 MPa depending on the ultrafiltration membrane used at that time. At this time, the liquid concentrated in the ultrafiltration device contains fat and protein. For example, when whey is used as a starting material, these protein concentrates are called whey protein concentrates and are now widely used for food. On the other hand, this primary ultrafiltration permeate is
It has limited use, whether it is concentrated and used to recover lactose or is discarded. The primary ultrafiltration permeate of these dairy raw materials contains 3 to 10 mg% of sialic acids.
二次限外濾過を行う前に、この一次限外濾過液を炭酸カ
ルシウム、水酸化カリウム、苛性ソーダ等のアルカリに
よりpH6.0〜8.0に調整してもよい。これにより処理能力
を向上させ、運転コストを低下させることができる。Before performing the secondary ultrafiltration, the primary ultrafiltrate may be adjusted to pH 6.0 to 8.0 with an alkali such as calcium carbonate, potassium hydroxide or caustic soda. As a result, the processing capacity can be improved and the operating cost can be reduced.
この一次限外濾過透過液を更に分画分子量の低い1,000
〜10,000ダルトンの二次限外濾過装置を用い低分子物質
である乳糖およびミネラルとシアル酸類とを分離する。
このとき、10,000ダルトンを超えると、シアル酸類が二
次限外濾過液に移行し、回収率が減少する。また、1,00
0ダルトンより細かいと、シアル酸類と低分子物質（乳
糖、ミネラル）との分離が悪くなり、純度をあげること
が出来ない。This first-order ultrafiltration permeate has a lower molecular weight cutoff of 1,000
A low molecular weight lactose and minerals and sialic acids are separated using a secondary ultrafiltration device of ~ 10,000 daltons.
At this time, if it exceeds 10,000 daltons, the sialic acids migrate to the secondary ultrafiltrate and the recovery rate decreases. Also 1,00
If it is smaller than 0 dalton, the separation of sialic acids and low molecular weight substances (lactose, minerals) will be poor and the purity cannot be increased.
このようにして、シアル酸類は二次限外濾過装置内に濃
縮される。この時の限外濾過装置の運転圧力は、その時
使用する限外濾過膜に応じ0.2〜2.0MPaで運転する。ま
た、この時10倍から15倍に濃縮した後、水を加える透析
濾過を実施してもよい。シアル酸含量およびミネラル含
量は、この透析濾過の度合いにより調節することができ
る。In this way, the sialic acids are concentrated in the secondary ultrafiltration device. The operating pressure of the ultrafiltration device at this time is 0.2 to 2.0 MPa depending on the ultrafiltration membrane used at that time. At this time, after concentrating 10 to 15 times, diafiltration may be carried out by adding water. The sialic acid content and mineral content can be adjusted by the degree of this diafiltration.
このシアル酸類濃縮液は、必要に応じて殺菌処理を行っ
た後、更に濃縮し、噴霧乾燥あるいは凍結乾燥により粉
体化する。This concentrated solution of sialic acids is subjected to sterilization treatment if necessary, then further concentrated, and powderized by spray drying or freeze drying.
このようにしてシアル酸類含有組成物は、シアル酸含量
２％以上および灰分５％以下の高品質のものが得られ
る。In this way, a high-quality sialic acid-containing composition having a sialic acid content of 2% or more and an ash content of 5% or less can be obtained.
得られたシアル酸類濃縮液を粉体化する前に、濃縮、冷
却し、乳糖の結晶化を行い、乳糖沈澱を除去し、更に純
度を上げることもできる。また、アニオン樹脂を用いて
シアル酸結合オリゴ糖を精製することもできる。更に、
ゲル濾過を行えば、ＧＭＰおよびシアル酸結合オリゴ糖
を分離精製することもできる。Before pulverizing the obtained concentrated solution of sialic acids, the solution can be concentrated and cooled to crystallize lactose to remove lactose precipitates and further improve the purity. The sialic acid-bound oligosaccharide can also be purified using an anion resin. Furthermore,
By performing gel filtration, GMP and sialic acid-bound oligosaccharide can be separated and purified.
（発明の効果） 上記の方法によって得られたシアル酸類含有組成物は、
育児用粉乳類、健康食品等の食品類に配合することによ
って、生理活性、例えば感染防御能あるいは学習能等の
向上が図れる。(Effect of the invention) The sialic acid-containing composition obtained by the above method,
By adding it to food products such as baby milk powder and health foods, it is possible to improve physiological activity, for example, infection prevention ability or learning ability.
以上述べたごとく、本発明によると本来牛乳中にある栄
養上有益なシアル酸類を各種乳質原料物質から工業的規
模で大量に、かつ経済的に取得することが可能になっ
た。As described above, according to the present invention, it is possible to economically obtain a large amount of nutritionally beneficial sialic acids originally contained in milk from various dairy raw materials on an industrial scale.
実施例１ ゴーダーチーズ製造時に排出されたホエーをクラリファ
イアーにかけ残留カゼインを分離し、次にクリームセパ
レーターにかけてクリームを分離した。Example 1 Whey discharged during the production of Gouda cheese was subjected to a clarifier to separate residual casein, and then to a cream separator to separate cream.
次に、このホエー液100をクエン酸でpH5.0に調整した
後、20,000ダルトンの分画分子量を有する限外濾過膜
（ローヌプーラン社製IRIS 3038）が装備された一次限
外濾過装置（0.88m2）を用い、運転圧力0.3MPaで10倍濃
縮まで限外濾過を実施した。得られた一次限外濾過透過
液90を苛性ソーダでpH6.5に調整し、5,000ダルトンの
分画分子量を有する限外濾過膜（Abcor社製HKF 131）
が装備された二次限外濾過装置（0.28m2）を用い、運転
圧力1.0MPaで10倍濃縮まで限外濾過を実施した。更に、
水を用いて３倍量の透析濾過を行い９のシアル酸類濃
縮物を得た。この濃縮液を減圧濃縮機にかけた後、凍結
乾燥を行い、白色のシアル酸類含有組成物200ｇを得
た。シアル酸類含有組成物のシアル酸含量は、2.5％で
あった。Next, after adjusting the pH of this whey solution 100 to 5.0 with citric acid, a primary ultrafiltration device (0.88) equipped with an ultrafiltration membrane (IRIS 3038 manufactured by Rhone Poulenc) having a cut-off molecular weight of 20,000 daltons was used. m 2 ), ultrafiltration was carried out at an operating pressure of 0.3 MPa up to 10 times concentration. The obtained primary ultrafiltration permeate 90 was adjusted to pH 6.5 with caustic soda, and the ultrafiltration membrane having a cut-off molecular weight of 5,000 daltons (HKF 131 manufactured by Abcor)
Using a secondary ultrafiltration device (0.28 m 2 ) equipped with, an ultrafiltration was performed at an operating pressure of 1.0 MPa up to 10 times concentration. Furthermore,
Dialysis filtration was performed with water three times to obtain a sialic acid concentrate of 9. The concentrated solution was applied to a vacuum concentrator and freeze-dried to obtain 200 g of a white sialic acid-containing composition. The sialic acid content of the sialic acid-containing composition was 2.5%.
実施例２ 牛乳をクリームセパレーターにかけてクリームを分離
し、脱脂乳を得た。Example 2 Milk was applied to a cream separator to separate the cream to obtain skim milk.
次に、この脱脂乳100を塩酸でpH5.5に調整した後500,
000ダルトンの分画分子量を有する限外濾過膜（DDS社製
GR 10PP）が装備された一次限外濾過装置（0.72m2）を
用い、運転圧力0.3MPaで10倍濃縮まで限外濾過を実施し
た。得られた一次限外濾過透過液90を炭酸カリウムで
pH6.5に調整し、2,000ダルトンの分画分子量を有する限
外濾過膜（DDS社製GR 90PP）が装備された二次限外濾
過装置（0.72m2）を用い、運転圧力1.0MPaで10倍濃縮ま
で限外濾過を実施した。更に、水を用いて５倍量の透析
濾過を行い９のシアル酸類濃縮物を得た。この濃縮液
を減圧濃縮機にかけた後、凍結乾燥を行い、白色のシア
ル酸類含有組成物100ｇを得た。このシアル酸類含有組
成物のシアル酸含量は、4.0％であった。Next, after adjusting the skim milk 100 to pH 5.5 with hydrochloric acid, 500,
Ultrafiltration membrane with a molecular weight cut-off of 000 Dalton (DDS)
Using a primary ultrafiltration device (0.72 m 2 ) equipped with GR 10PP), ultrafiltration was performed up to 10 times concentration at an operating pressure of 0.3 MPa. The resulting primary ultrafiltration permeate 90 was diluted with potassium carbonate.
Using a secondary ultrafiltration device (0.72 m 2 ) equipped with an ultrafiltration membrane (GR 90PP manufactured by DDS) adjusted to pH 6.5 and having a molecular weight cut-off of 2,000 daltons, operating pressure 1.0 MPa Ultrafiltration was performed until doubling concentration. Further, diafiltration of 5 volumes was performed using water to obtain a sialic acid concentrate of 9. This concentrated solution was applied to a vacuum concentration machine and then freeze-dried to obtain 100 g of a white sialic acid-containing composition. The sialic acid content of this sialic acid-containing composition was 4.0%.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 井門 和夫 東京都日野市日野2940―１番地 (56)参考文献 特開 昭51−91358（ＪＰ，Ａ) 特開 昭51−105015（ＪＰ，Ａ) ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Kazuo Imon 2940-1 Hino, Hino City, Tokyo (56) References JP-A-51-91358 (JP, A) JP-A-51-105015 (JP, A)
Claims (1)
0〜6.0に調整して20,000〜500,000ダルトンの分画分子
量を有する限外濾過装置を用い一次限外濾過を行い、こ
れから得られた限外濾過透過液を更にpH6.0〜8.0に調整
して1,000〜10,000ダルトンの分画分子量を有する限外
濾過装置を用いて二次限外濾過を行い、低分子物質を除
去することを特徴とするシアル酸類含有組成物の製造
法。1. A dairy raw material containing sialic acids having a pH of 4.
Performed primary ultrafiltration using an ultrafiltration device having a molecular weight cut-off of 20,000 to 500,000 daltons adjusted to 0 to 6.0, and the ultrafiltration permeate obtained therefrom was further adjusted to pH 6.0 to 8.0. A method for producing a sialic acid-containing composition, which comprises performing secondary ultrafiltration by using an ultrafiltration device having a molecular weight cutoff of 1,000 to 10,000 daltons to remove low-molecular substances.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62325500A JPH0631286B2 (en) | 1987-12-24 | 1987-12-24 | Method for producing sialic acid-containing composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62325500A JPH0631286B2 (en) | 1987-12-24 | 1987-12-24 | Method for producing sialic acid-containing composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01168693A JPH01168693A (en) | 1989-07-04 |
| JPH0631286B2 true JPH0631286B2 (en) | 1994-04-27 |
Family
ID=18177571
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62325500A Expired - Fee Related JPH0631286B2 (en) | 1987-12-24 | 1987-12-24 | Method for producing sialic acid-containing composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0631286B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2010301762B2 (en) * | 2009-09-29 | 2016-04-21 | Megmilk Snow Brand Co., Ltd. | Method for separating sialyllactose material |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3035833B2 (en) * | 1991-01-21 | 2000-04-24 | 雪印乳業株式会社 | Method for producing sialic acids-containing composition |
| JPH0899988A (en) * | 1994-09-29 | 1996-04-16 | Takehiko Yamamoto | Production of oligosaccharide containing sialic acids |
| US6288222B1 (en) * | 2000-02-16 | 2001-09-11 | Neose Technologies, Inc. | Method of filtration of a dairy stream |
| DK1951060T3 (en) * | 2005-11-04 | 2018-01-29 | Arla Foods Amba | CONCENTRATE derived from a milk product enriched with naturally occurring sialyl lactose and a process for its preparation |
| GB0904562D0 (en) * | 2009-03-17 | 2009-04-29 | Separation Technologies Invest | Isolation and purification of components of whey |
| JP5599994B2 (en) * | 2009-09-29 | 2014-10-01 | 雪印メグミルク株式会社 | Separation method of sialyl lactose material |
| JP5812455B2 (en) * | 2014-07-15 | 2015-11-11 | 雪印メグミルク株式会社 | Separation method of sialyl lactose material |
| AU2017326654C1 (en) * | 2016-09-19 | 2022-07-21 | Prolacta Bioscience, Inc. | Purified human milk oligosaccharides compositions |
| JP7372232B2 (en) * | 2018-03-30 | 2023-10-31 | 雪印メグミルク株式会社 | Method for producing a composition containing κ-casein glycomacropeptide |
| CN109797468A (en) * | 2019-02-26 | 2019-05-24 | 浙江久大纺织科技有限公司 | A kind of preparation method of fire-retardant flocking yarn |
| TW202126317A (en) | 2019-09-24 | 2021-07-16 | 美商普拉塔生技公司 | Compositions and methods for treatment of inflammatory and immune diseases |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2288477A1 (en) * | 1974-10-22 | 1976-05-21 | Manche Union Coop Agr Laiti | PROCESS FOR THE PRODUCTION OF SIALIC ACID AND GLYCOPROTEINS FROM CHEESE WHEY |
| FR2288473A1 (en) * | 1974-10-22 | 1976-05-21 | Manche Union Coop Agr Laiti | PROCESS FOR TREATMENT OF CHEESE WHEY, IN PARTICULAR WITH A VIEW OF THE EXTRACTION OF GLYCOPROTEIDES AND SIALIC ACID |
-
1987
- 1987-12-24 JP JP62325500A patent/JPH0631286B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2010301762B2 (en) * | 2009-09-29 | 2016-04-21 | Megmilk Snow Brand Co., Ltd. | Method for separating sialyllactose material |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01168693A (en) | 1989-07-04 |
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