JPH07103138B2 - Method for preparing sialic acid - Google Patents
Method for preparing sialic acidInfo
- Publication number
- JPH07103138B2 JPH07103138B2 JP18901587A JP18901587A JPH07103138B2 JP H07103138 B2 JPH07103138 B2 JP H07103138B2 JP 18901587 A JP18901587 A JP 18901587A JP 18901587 A JP18901587 A JP 18901587A JP H07103138 B2 JPH07103138 B2 JP H07103138B2
- Authority
- JP
- Japan
- Prior art keywords
- sialic acid
- meconium
- chick
- acid
- preparing
- 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 - Lifetime
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 37
- 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 37
- 238000000034 method Methods 0.000 title claims description 6
- 210000001006 meconium Anatomy 0.000 claims description 14
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 239000003957 anion exchange resin Substances 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- 238000000909 electrodialysis Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 238000001179 sorption measurement Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229930014626 natural product Natural products 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- HVCOBJNICQPDBP-UHFFFAOYSA-N 3-[3-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxydecanoyloxy]decanoic acid;hydrate Chemical compound O.OC1C(OC(CC(=O)OC(CCCCCCC)CC(O)=O)CCCCCCC)OC(C)C(O)C1OC1C(O)C(O)C(O)C(C)O1 HVCOBJNICQPDBP-UHFFFAOYSA-N 0.000 description 2
- 229930186217 Glycolipid Natural products 0.000 description 2
- 102000003886 Glycoproteins Human genes 0.000 description 2
- 108090000288 Glycoproteins Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 210000000436 anus Anatomy 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 108090000623 proteins and genes Chemical group 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 102000018265 Virus Receptors Human genes 0.000 description 1
- 108010066342 Virus Receptors Proteins 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 239000003172 expectorant agent Substances 0.000 description 1
- 230000003419 expectorant effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002632 lipids Chemical group 0.000 description 1
- CERZMXAJYMMUDR-UHFFFAOYSA-N neuraminic acid Natural products NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO CERZMXAJYMMUDR-UHFFFAOYSA-N 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical group 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明は、ヒヨコ胎便中に含有されているシアル酸を有
利に分離して採取するシアル酸の調製法に関する。TECHNICAL FIELD The present invention relates to a method for preparing sialic acid in which sialic acid contained in chick meconium is advantageously separated and collected.
技術的背景 シアル酸は、ノイラミン酸のアシル誘導体の総称で、血
液タンパク質の血中半減期の制御活性、ウイルスのレセ
プター活性、去痰活性等を有し、生理上重要な役割を果
たしている有用な物質である。Technical background Sialic acid is a general term for acyl derivatives of neuraminic acid, and has useful functions that have physiological physiologically important roles, such as blood protein half-life control activity, virus receptor activity, and expectorant activity. Is.
また、シアル酸は、糖タンパク質や糖脂質の非還元末端
に結合して存在していることから、近年、糖タンパク質
や糖脂質の合成原料としても有用とされている。In addition, since sialic acid exists by binding to the non-reducing end of glycoprotein or glycolipid, it has recently been regarded as useful as a raw material for synthesizing glycoprotein or glycolipid.
一方、シアル酸は、動物を主体として自然界に広く分布
されているものの、シアル酸を含有する天然物から工業
的規模でしかも高純度で調製することは困難であるた
め、その入手が容易でないのが現状である。On the other hand, although sialic acid is widely distributed in nature mainly in animals, it is difficult to obtain sialic acid from a natural product containing sialic acid on an industrial scale and in high purity, and thus it is not easily available. Is the current situation.
したがつて、シアル酸含有天然物からシアル酸を高純度
で有利に調製し得る方法の開発が要望されている。Therefore, there is a demand for development of a method capable of advantageously preparing sialic acid from a sialic acid-containing natural product with high purity.
発明が解決しようとする課題 本発明者は、叙上の状況に鑑み、シアル酸を含有する天
然物及びそれからシアル酸の分離について検討した結
果、ヒヨコの雌雄鑑別の際にヒヨコの肛門から除去され
る胎便中にシアル酸が比較的高濃度で含まれており、か
つ該胎便を加水分解することにより、それに含まれるシ
アル酸が有利に分離されることの知見を得て、本発明を
なすに至つた。DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention In view of the above circumstances, the present inventor has studied the natural product containing sialic acid and the separation of sialic acid from the natural product, and as a result, it was removed from the anus of the chick at the time of male and female discrimination of the chick. The meconium contained in meconium at a relatively high concentration was obtained, and it was found that the sialic acid contained therein is advantageously separated by hydrolysis of the meconium. It arrived.
したがつて、本発明は、ヒヨコ胎便を出発原料として用
い、それを加水分解することにより、それに含有される
シアル酸を分離、採取してシアル酸を高純度で有利に得
るための調製法を提供することを課題とする。Therefore, the present invention uses a chick meconium as a starting material, and by hydrolyzing it, a sialic acid contained therein is separated and collected to provide a preparation method for advantageously obtaining sialic acid with high purity. The challenge is to provide.
以下本発明を詳しく説明する。The present invention will be described in detail below.
発明の構成 本発明の特徴は、ヒヨコ胎便を加水分解して、それに含
有されるシアル酸を遊離させて得られるシアル酸含有液
を、アニオン交換樹脂に通してシアル酸を該樹脂に吸着
させ、ついでこの吸着シアル酸を溶出して得られる液を
電気透析により精製して採取することにある。The features of the present invention include hydrolyzing chick meconium, sialic acid-containing liquid obtained by releasing the sialic acid contained therein, pass an anion exchange resin to adsorb sialic acid to the resin, Then, a liquid obtained by eluting the adsorbed sialic acid is purified by electrodialysis and collected.
課題を解決するための手段 本発明において出発原料として用いるヒヨコ胎便は、前
述のように、ヒヨコの雌雄鑑別の際に肛門より除去され
るものであつて、シアル酸を比較的高濃度で含有してい
る。Means for Solving the Problems As described above, the chick meconium used as a starting material in the present invention is one that is removed from the anus during sexing of chicks and contains sialic acid in a relatively high concentration. ing.
ヒヨコ胎便中のシアル酸は、遊離形態のほかは、オリゴ
糖、タンパク質及び脂質に結合した形態で存在している
ため、これらに結合のシアル酸を遊離させる必要があ
る。Since sialic acid in chick meconium exists in a free form as well as a form bound to oligosaccharides, proteins and lipids, it is necessary to release the bound sialic acid.
本発明では、ヒヨコ胎便を加水分解することにより、上
記シアル酸を遊離させるものであつて、この加水分解
は、塩酸、硫酸、リン酸等の酸を出発原料としての胎便
に対し0.05N〜2.0Nになるように添加して、80〜100℃の
温度で15〜120分間程度行うのが好ましい。In the present invention, chick meconium is hydrolyzed to release the sialic acid, and the hydrolysis is 0.05 N to 2.0% with respect to meconium starting from an acid such as hydrochloric acid, sulfuric acid or phosphoric acid. It is preferable to add N so that the temperature is 80 to 100 ° C. for about 15 to 120 minutes.
上記加水分解により、ヒヨコ胎便なかのシアル酸は実質
上遊離されるので、得られる加水分解液を濾別した後、
アニオン交換樹脂に通して該液中のシアル酸を吸着させ
る。By the above hydrolysis, sialic acid in chick meconium is substantially released, so after filtering the resulting hydrolysis solution,
The sialic acid in the liquid is adsorbed by passing through an anion exchange resin.
ここで用いるアニオン交換樹脂としてはダウエツクス１
×２、ダウエツクス２、アンバーライトIRA 410等を例
示し得る。The anion exchange resin used here is Dowex 1
X2, Dowex 2, Amberlite IRA 410 and the like can be exemplified.
次に、上記通液によりアニオン交換樹脂に選択吸着され
たシアル酸を溶出する。この溶出は、塩酸又は食塩等の
0.1〜0.3Mの水溶液を用いて行うとよい。Next, the sialic acid selectively adsorbed on the anion exchange resin is eluted by the above-mentioned passage. This elution is performed with hydrochloric acid or salt.
It is recommended to use an aqueous solution of 0.1 to 0.3M.
このようにして溶出して得られる液を、電気透析に付し
て脱塩処理を行うことにより、高純度のシアル酸を得る
ことができる。The solution obtained by elution in this way is subjected to electrodialysis and desalted to obtain high-purity sialic acid.
以下に実施例を示して本発明及びその効果を具体的に説
明する。The present invention and its effects will be specifically described below with reference to examples.
実施例 ヒヨコ胎便1kgに濃硫酸2mlを添加してpH2に調整した
後、92℃で60分間加熱して加水分解を行つた。得られた
加水分解液を遠心分離して加熱により凝固したタンパク
質を除去した後、ダウエツクス１×２（OH型）を充填し
たカラム（500ml容）に通してシアル酸を該樹脂に吸着
させた。次いで、この樹脂に十分量の水を通液して樹脂
に吸着しない不純物を流出させた後、２％食塩水溶液1.
5lを通して吸着したシアル酸を溶出させた。得られた溶
出液を電気透析装置（徳山曹達（株）社製）を用いて、
電気伝導度が−500μS/cmまで脱塩した。脱塩終了後、
脱塩液を減圧濃縮して凍結乾燥を行つて白色粉末250mg
を得た。Example After adding 2 ml of concentrated sulfuric acid to 1 kg of chick meconium to adjust the pH to 2, hydrolysis was performed by heating at 92 ° C. for 60 minutes. The resulting hydrolyzed solution was centrifuged to remove proteins coagulated by heating, and then passed through a column (500 ml volume) packed with Dowex 1 × 2 (OH type) to adsorb sialic acid on the resin. Then, a sufficient amount of water was passed through this resin to allow impurities not adsorbed by the resin to flow out, and then a 2% saline solution 1.
The adsorbed sialic acid was eluted through 5 l. The obtained eluate was electrolyzed (manufactured by Tokuyama Soda Co., Ltd.),
It was desalted to an electric conductivity of −500 μS / cm. After desalination,
The desalted solution was concentrated under reduced pressure and freeze-dried to obtain 250 mg of white powder.
Got
このようにして得られた粉末のシアル酸純度は、チオバ
ルビツール法による測定で約95％であつた。The sialic acid purity of the powder thus obtained was about 95% as measured by the thiobarbitur method.
Claims (2)
れているシアル酸を遊離させて得られるシアル酸含有液
を、アニオン交換樹脂に通してシアル酸を該樹脂に吸着
させ、次いでこの吸着シアル酸を溶出して得られる液を
電気透析により精製処理してシアル酸を得ることを特徴
とするシアル酸の調製法。1. A sialic acid-containing liquid obtained by hydrolyzing chick meconium to release sialic acid contained therein, is passed through an anion exchange resin to adsorb sialic acid on the resin, and then the adsorption is carried out. A method for preparing sialic acid, characterized in that a solution obtained by eluting sialic acid is purified by electrodialysis to obtain sialic acid.
2.0Nの酸を添加し、80〜100℃の温度で15〜120分間加熱
して行う特許請求の範囲第（１）項記載のシアル酸の調
製法。2. Hydrolysis is performed in the range of 0.05N to chick meconium.
The method for preparing sialic acid according to claim (1), wherein 2.0N acid is added and heating is performed at a temperature of 80 to 100 ° C. for 15 to 120 minutes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18901587A JPH07103138B2 (en) | 1987-07-30 | 1987-07-30 | Method for preparing sialic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18901587A JPH07103138B2 (en) | 1987-07-30 | 1987-07-30 | Method for preparing sialic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6434995A JPS6434995A (en) | 1989-02-06 |
| JPH07103138B2 true JPH07103138B2 (en) | 1995-11-08 |
Family
ID=16233874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18901587A Expired - Lifetime JPH07103138B2 (en) | 1987-07-30 | 1987-07-30 | Method for preparing sialic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07103138B2 (en) |
-
1987
- 1987-07-30 JP JP18901587A patent/JPH07103138B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6434995A (en) | 1989-02-06 |
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