JPH06102672B2 - Method for producing sialic acid - Google Patents
Method for producing sialic acidInfo
- Publication number
- JPH06102672B2 JPH06102672B2 JP2235434A JP23543490A JPH06102672B2 JP H06102672 B2 JPH06102672 B2 JP H06102672B2 JP 2235434 A JP2235434 A JP 2235434A JP 23543490 A JP23543490 A JP 23543490A JP H06102672 B2 JPH06102672 B2 JP H06102672B2
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- sialic acid
- acid
- egg yolk
- hydrolysis
- defatted
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- Saccharide Compounds (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、鶏の卵黄から極性脂質，中性脂質，コレステ
ロール等を製造した際、その残渣として得られる脱脂卵
黄を原料としてシアル酸を大量に製造する方法に関す
る。DETAILED DESCRIPTION OF THE INVENTION [Industrial field of application] The present invention relates to the production of polar lipids, neutral lipids, cholesterol and the like from chicken egg yolk, and uses defatted egg yolk as a raw material to produce a large amount of sialic acid. To the manufacturing method.
シアル酸は、ノイラミン酸の総称で自然界には多くの種
類の誘導体が存在する。そのうち主なものは、Ｎ−アセ
チルノイラミン酸である。Sialic acid is a general term for neuraminic acid, and many kinds of derivatives exist in nature. The main one is N-acetylneuraminic acid.
近年、シアル酸はウイルスのレセプターの役割，コレラ
毒素の中和活性，病原性大腸菌の感染抑制，去痰活性，
血液タンパク質の血中半減期の制御等に関与することが
知られており、医薬用への需要が高まりつつある。Recently, sialic acid plays a role of virus receptor, cholera toxin neutralizing activity, infection control of pathogenic Escherichia coli, expectorant activity,
It is known to be involved in controlling the blood half-life of blood proteins, and the demand for pharmaceuticals is increasing.
シアル酸は、生体中で糖タンパク質や糖脂質の非還元末
端に存在し自然界に広く分布しているもののシアル酸を
含有する天然物から大量にしかも安価に製造することは
困難である。Although sialic acid exists in the non-reducing end of glycoproteins and glycolipids in the living body and is widely distributed in nature, it is difficult to mass-produce sialic acid from a natural product containing sialic acid at low cost.
従来、シアル酸の製造法として、ヒヨコ胎便からの製造
（昭和64年特許出願公開第34995号），鶏卵白より得た
カラザおよびオボムチンからの製造（昭和43年特許出願
広告第16042号）等が報告されてはいるが、これらは、
原料の工業的供給体制が確立されておらず、工業的に大
量にしかも安価にシアル酸を製造することが不可能であ
った。Conventionally, as a method for producing sialic acid, production from chick meconium (patent application publication No. 34995 in 1988), karaza obtained from egg white and ovomucin (patent application advertisement No. 16042 in 1968), etc. Although reported, these are
Since the industrial supply system of raw materials has not been established, it has been impossible to industrially produce sialic acid in large quantities and at low cost.
一方、卵黄中にシアル酸が存在することは知られてい
た。しかし、卵黄は食品用原料としてマヨネーズ，ケー
キ等に使用されているのみで、卵黄中の成分の工業的な
利用については、唯一卵黄脂質が化粧品，医薬品及び一
部食品用素材とし用いられているにすぎず、卵黄からシ
アル酸を工業的に分離しようとする試みは全く行われて
いなかった。On the other hand, it was known that sialic acid was present in egg yolk. However, egg yolk is only used as a raw material for food in mayonnaise, cakes, etc. For the industrial use of the ingredients in egg yolk, the only yolk lipid is used as a material for cosmetics, pharmaceuticals and some foods. However, no attempt has been made to industrially separate sialic acid from egg yolk.
その理由として、卵黄からシアル酸を分離する場合、多
量に含まれる脂質のために、加水分解後の卵黄液が強い
乳化状態となり、その後の精製工程に大きな障害となる
ため、シアル酸の製造工程をはん雑にし、かつコスト的
にも有利な原料とはいい難い欠点を有していた。The reason is that when sialic acid is separated from egg yolk, the lipid contained in a large amount causes the yolk liquid after hydrolysis to be in a strong emulsified state, which is a major obstacle to the subsequent purification process, and therefore the sialic acid production process. Had a drawback that it was difficult to call it a raw material which was complicated and cost effective.
本発明はシアル酸を大量にしかも安価に製造する方法を
確立し、提供することを目的とする。An object of the present invention is to establish and provide a method for producing sialic acid in a large amount and at low cost.
本発明者らは、上述の実状に鑑みシアル酸の製造法につ
き鋭意研究を重ねた結果、シアル酸含有量が高く安価で
しかも大量に供給可能な原料として、卵黄脂質を抽出し
た残渣が有効利用されず、わずかに家畜用飼料に使用さ
れているのみで、その大部分は産業廃棄物として廃棄さ
れていることに着目し、脱脂卵黄を加水分解した後、常
法により吸着分離等の精製を行うことで容易にシアル酸
が得られることを見い出し本発明を完成させるに到っ
た。As a result of intensive studies on the method for producing sialic acid in view of the above situation, the present inventors have found that the residue obtained by extracting egg yolk lipids is effectively used as a raw material that has a high sialic acid content and is inexpensive and can be supplied in large quantities. However, focusing on the fact that most of the waste is used as livestock feed and most of it is discarded as industrial waste, after hydrolyzing the defatted egg yolk, purification such as adsorption separation is performed by a conventional method. It was found that sialic acid can be easily obtained by carrying out the present invention and completed the present invention.
即ち、本発明は脱脂卵黄を加水分解することを特徴とす
るシアル酸の製造法に関する。That is, the present invention relates to a method for producing sialic acid, which comprises hydrolyzing defatted egg yolk.
以下に本発明を詳述する。The present invention is described in detail below.
本発明のシアル酸とはノイラミン酸類化合物の内、特に
Ｎ−アセチルノイラミン酸,N−アセチルノイラミン酸結
合オリゴ糖を指し、Ｎ−アセチルノイラミン酸の含有量
は、特に制限するものではないが、少なくとも上述のシ
アル酸がそれぞれ遊離の状態で存在する必要がある。The sialic acid of the present invention refers to N-acetylneuraminic acid, N-acetylneuraminic acid-bonded oligosaccharides among neuraminic acid compounds, and the content of N-acetylneuraminic acid is not particularly limited. However, at least the above-mentioned sialic acid must be present in a free state.
本発明の脱脂卵黄とは、生卵黄，乾燥粉末卵黄等から有
機溶媒（例えばメタノール，ジメチルエーテル等）を用
い常法により脱脂された卵黄をさし、全固形分当りの許
容される残存脂質の量は、20％以下であれば良く、好ま
しくは、10％以下のものが好適に用いられる。The defatted egg yolk of the present invention refers to egg yolk defatted by a conventional method using an organic solvent (eg, methanol, dimethyl ether, etc.) from raw egg yolk, dried powder egg yolk, etc., and the amount of residual lipids permissible per total solid content. Is 20% or less, preferably 10% or less.
加水分解は、脱脂卵黄中シアル酸を遊離の状態にする為
必須の工程であり、加水分解には酸加水分解もしくは酵
素による加水分解が適用できる。Hydrolysis is an essential step for making sialic acid in defatted egg yolk in a free state, and acid hydrolysis or enzymatic hydrolysis can be applied to the hydrolysis.
加水分解の条件は、酸加水分解法の場合、脱脂卵黄液に
硫酸，塩酸等の酸を添加しpHを0.6〜2.5に調整後、70〜
90℃で30〜120分間加熱した後、硫酸バリウム，水酸化
カルシウム等の中和剤によって中和すればよい。上述の
範囲をはずれる場合には、シアル酸の遊離が不完全にな
るかまたはシアル酸の分解を生ずるため不都合である。In the case of the acid hydrolysis method, the conditions for hydrolysis are 70 to 70% after adjusting the pH to 0.6 to 2.5 by adding acid such as sulfuric acid and hydrochloric acid to the defatted egg yolk liquid.
After heating at 90 ° C for 30 to 120 minutes, it may be neutralized with a neutralizing agent such as barium sulfate or calcium hydroxide. When it is out of the above range, the release of sialic acid becomes incomplete or the sialic acid is decomposed, which is disadvantageous.
また、酵素による加水分解では、目的に応じノイラミニ
ダーゼ，プロテアーゼ，糖加水分解酵素等の酵素の一種
または二種以上を選択し、各酵素の至適条件にて反応後
酵素を加熱等により失活させればよい。In addition, in the case of enzymatic hydrolysis, one or more enzymes such as neuraminidase, protease, and sugar hydrolase are selected according to the purpose, and the enzyme is inactivated by heating after the reaction under the optimal conditions for each enzyme. Just do it.
すなわち、ノイラミンダーゼによりＮ−アセチルノイラ
ミン酸が遊離し、プロテアーゼにより各種Ｎ−アセチル
ノイラミン酸結合オリゴ糖が得られる。That is, N-acetylneuraminic acid is released by neuraminidase, and various N-acetylneuraminic acid-linked oligosaccharides are obtained by protease.
次いで得られた加水分解液は、過または遠心分離によ
る不溶物を除去した後、必要により減圧濃縮し噴霧乾
燥，凍結乾燥等通常用いられる方法により乾燥すること
で粗製シアル酸を得ることができる。さらに、高純度の
シアル酸を得ようとする場合、加水分解液を過または
遠心分離し不溶物を除去した後、吸着剤によりシアル酸
を分離精製できる。吸着剤としては、陽イオン交換樹脂
と陰イオン交換樹脂を用いる。まず、不溶物を除去した
加水分解液を陽イオン交換樹脂に通して夾雑物の吸着さ
せ、さらに陰イオン交換樹脂にシアル酸を吸着させる。
ここで用いる陽イオン交換樹脂としては、ダウエックス
50W-X2,アンバーライトIR-116,ダイヤイオンSK102等ま
た陰イオン交換樹脂としては、ダウエックス１×8,アン
バーライトIRA401,ダイヤイオンSA11A等をあげることが
できる。The resulting hydrolyzed solution is then subjected to removal of insoluble matter by excess or centrifugation, and if necessary, concentrated under reduced pressure and dried by a commonly used method such as spray drying or freeze drying to obtain crude sialic acid. Further, in order to obtain high-purity sialic acid, the hydrolyzed solution may be subjected to excess or centrifugation to remove insoluble matter, and then sialic acid can be separated and purified with an adsorbent. As the adsorbent, a cation exchange resin and an anion exchange resin are used. First, the hydrolyzed liquid from which the insoluble matter has been removed is passed through a cation exchange resin to adsorb the contaminants, and further sialic acid is adsorbed to the anion exchange resin.
The cation exchange resin used here is Dowex
50W-X2, Amberlite IR-116, Diaion SK102, etc. As the anion exchange resin, Dowex 1 × 8, Amberlite IRA401, Diaion SA11A and the like can be mentioned.
陰イオン交換樹脂に吸着させたシアル酸は、ギ酸もしく
は塩酸濃度を０〜2Nまで、あるいは、食塩濃度を０〜1N
までの範囲で溶出させ回収する。Sialic acid adsorbed on an anion exchange resin has a formic acid or hydrochloric acid concentration of 0 to 2N or a salt concentration of 0 to 1N.
Elute in the range up to and collect.
このシアル酸溶出液は必要であれば、ゲル過，電気透
折等の常法により脱塩処理した後、減圧乾燥、噴霧乾燥
あるいは凍結乾燥することにより高純度のシアル酸を得
ることができる。If necessary, the sialic acid eluate may be desalted by a conventional method such as gel filtration or electrodialysis, and then dried under reduced pressure, spray-dried or freeze-dried to obtain high-purity sialic acid.
以下に実施例を示し、本発明をより具体的に説明する。Hereinafter, the present invention will be described more specifically with reference to examples.
試験例１（脱脂卵黄の調整，脂質の定量及び乳化試験） 卵黄粉末100gを冷却管をつけたナスフラスコで50℃に温
め以下の条件にて脱脂を行った。Test Example 1 (Adjustment of defatted egg yolk, quantification of lipids and emulsification test) 100 g of egg yolk powder was warmed to 50 ° C. in a eggplant flask equipped with a cooling tube and degreased under the following conditions.
尚、ジエチルエーテルのみ、32℃にて脱脂を行った。Incidentally, only diethyl ether was degreased at 32 ° C.
結果を第１表に示す。The results are shown in Table 1.
上記脱脂卵黄Ａ〜Ｌ及び未脱脂卵黄各々50gを室温中で
アセトン500ml,2回、さらに冷却管をつけ50℃でクロロ
ホルム：メタノール（2:1）500ml,2回、脂質を抽出し脂
質の定量を行った。さらに、脱脂卵黄Ａ〜Ｌ及び未脱脂
卵黄を各々10gとり、0.1N硫酸30mlを加えホモミキサー
で撹拌後、80℃にて１時間加水分解を行い、さらに、飽
和水酸化バリウム溶液にてpH5.0に調整し、過した。
その液の乳化状態を調べた。 The defatted egg yolks A to L and 50 g each of non-defatted egg yolks were subjected to quantification of lipids by extracting the lipids at room temperature with 500 ml of acetone twice, and with a cooling tube at 50 ° C. with chloroform: methanol (2: 1) 500 ml twice. I went. Further, 10 g of defatted egg yolks A to L and 10 g of each non-defatted egg yolk were added, 30 ml of 0.1N sulfuric acid was added, and the mixture was stirred with a homomixer, hydrolyzed at 80 ° C for 1 hour, and further saturated with barium hydroxide solution to pH 5. Adjusted to 0 and passed.
The emulsified state of the liquid was examined.
結果を第２表に示す。The results are shown in Table 2.
上記の試験結果より中性脂質，リン脂質を合せた総脂質
含量が20％以下の場合は乳化状態を呈せず、その後の製
造プロセスに支障を来たすことはない。 From the above test results, when the total lipid content of neutral lipids and phospholipids is 20% or less, the emulsified state is not exhibited and the subsequent manufacturing process is not hindered.
実施例.1 試験例１の脱脂卵黄B40kgを水300lに懸濁させ、次いで6
N硫酸を加えpH1.4に調整、80℃で60分間ゆるく撹拌しな
がら酸加水分解を行った。加水分解後、飽和水酸化バリ
ウム溶液を加え、pH5.0に調整した。これを加圧過器
にて、不溶物を除去した後、減圧濃縮しシアル酸2.7kg
（収率6.75％）を得た。レゾルシノール法にて、Ｎ−ア
セチルノイラミン酸含量を測定した所、41.4％であっ
た。Example.1 40 kg of defatted egg yolk B of Test Example 1 was suspended in 300 l of water, and then 6
N sulfuric acid was added to adjust the pH to 1.4, and acid hydrolysis was carried out at 80 ° C for 60 minutes with gentle stirring. After hydrolysis, saturated barium hydroxide solution was added to adjust the pH to 5.0. After removing insoluble matter with a pressurizer, it was concentrated under reduced pressure to give 2.7 kg of sialic acid.
(Yield 6.75%) was obtained. The N-acetylneuraminic acid content measured by the resorcinol method was 41.4%.
実施例.2 試験例１の脱脂卵黄C40kgを水300lに懸濁させ、プロテ
アーゼ［シグマ社製,Protease from Papaya（TypeII
I）］1.0kgを加えpH7.3、温度37℃で12時間反応させた
後90℃で10分間加熱し、酵素を失活させた。この加水分
解液を連続遠心分離機にて沈澱を除去しその上清を噴霧
乾燥し、シアル酸（Ｎ−アセチルノイラミン酸結合オリ
ゴ糖）4.7kg（収率11.7％）を得た。このシアル酸のＮ
−アセチルノイラミン酸を遊離させるため、酸加水分解
し、レゾルシノール法にてＮ−アセチルノイラミン酸含
量を測定した所、23.5％であった。Example 2 40 g of defatted egg yolk C of Test Example 1 was suspended in 300 l of water, and a protease [Protease from Papaya (TypeII
I)] 1.0 kg was added and reacted at pH 7.3 and temperature 37 ° C for 12 hours, and then heated at 90 ° C for 10 minutes to inactivate the enzyme. A precipitate was removed from the hydrolyzed solution by a continuous centrifuge, and the supernatant was spray-dried to obtain 4.7 kg of sialic acid (N-acetylneuraminic acid-bound oligosaccharide) (yield 11.7%). N of this sialic acid
-To release acetylneuraminic acid, acid hydrolysis was performed, and the N-acetylneuraminic acid content measured by the resorcinol method was 23.5%.
実施例.3 試験例１の脱脂卵黄F40kgを水300lに懸濁させ、ノイラ
ミニターゼ［生化学工業（株）,Neuraminidase（Strept
ococcus sp.）］600gを加え、pH温度37℃で15時間反応
させた後、90℃で10分間加熱し、酵素を失活させた。こ
れを加圧過器にて不溶物を除去した後、ダウエックス
50W-X2（Ｈ型,1）を充填したカラムに通しさらにダウ
エックス１×８（ギ酸型,3l）の樹脂を充填したカラム
に通し、シアル酸を樹脂に吸着させた。その後、水500l
で夾雑物を洗浄した。ギ酸濃度０〜2Nの溶出液を用い、
シアル酸をグラジェント溶出した。シアル酸含有フラク
ションを集め、減圧乾固した。さらに、この乾固物を水
500mlに溶解させ、凍結乾燥を行い、シアル酸43g（収
率,0.11％）を得た。Ｎ−アセチルノイラミン酸の純度
はチオバルビツール酸による測定で約98％であった。Example 3 40 kg of defatted egg yolk F of Test Example 1 was suspended in 300 l of water, and neuraminidase (Seikagaku Corporation, Neuraminidase (Strept
ococcus sp.)] was added and reacted at pH temperature of 37 ° C. for 15 hours, and then heated at 90 ° C. for 10 minutes to inactivate the enzyme. After removing insoluble matter with a pressurizer, Dowex
It was passed through a column packed with 50W-X2 (H type, 1) and further through a column packed with resin of Dowex 1 × 8 (formic acid type, 3 l) to adsorb sialic acid on the resin. Then 500 l of water
The foreign matters were washed with. Using an eluate with a formic acid concentration of 0 to 2N,
Sialic acid was gradient eluted. Fractions containing sialic acid were collected and dried under reduced pressure. In addition, dry this solid matter with water.
It was dissolved in 500 ml and freeze-dried to obtain 43 g of sialic acid (yield, 0.11%). The purity of N-acetylneuraminic acid was about 98% as measured by thiobarbituric acid.
実施例.4 脱脂卵黄C40kgを水300lに懸濁させ、次いで6N硫酸を加
えpH1.4に調整、80℃で60分間ゆるく撹拌しながら酸加
水分解を行った。加水分解後、飽和水酸化バリウム溶液
を加えpH5.0に調整した。これを加圧過器にて不溶物
を除去した後、ダウエックス50W−×２（Ｈ型,1）を
充填しカラムに通し、さらにダウエックス１×８（ギ酸
型,3l）の樹脂を充填したカラムに通してシアル酸を樹
脂に吸着させた。その後、水500lで洗浄した。シアル酸
の溶出は、実施例３と同様に行い凍結乾燥後シアル酸48
g（収率,0.12％）を得た。Ｎ−アセチルノイラミン酸の
純度はチオバルビツール酸法による測定で約96％であっ
た。Example 4 4 40 kg of defatted egg yolk C was suspended in 300 l of water, then 6N sulfuric acid was added to adjust the pH to 1.4, and acid hydrolysis was carried out at 80 ° C. for 60 minutes with gentle stirring. After hydrolysis, saturated barium hydroxide solution was added to adjust the pH to 5.0. After removing the insoluble matter with a pressurizer, it was filled with Dowex 50W- × 2 (H type, 1) and passed through a column, and further filled with Dowex 1 × 8 (formic acid type, 3l) resin. The sialic acid was adsorbed on the resin through the column. Then, it was washed with 500 l of water. Elution of sialic acid was performed in the same manner as in Example 3, and after lyophilization, sialic acid 48 was added.
g (yield, 0.12%) was obtained. The purity of N-acetylneuraminic acid was about 96% as measured by the thiobarbituric acid method.
実施例.5 脱脂卵黄L20kgを水150lに懸濁させ、次いで6N硫酸を加
えpH1.4に調整、80℃で60分間ゆるく撹拌しながら酸加
水分解を行った。加水分解後、石灰乳［CaCO3:Ca（OH）
2＝1:1］を加えpH5.0に調整した。これを加圧過器に
て不溶物を除去した後、アンバーライトIR-116を充填し
たカラムに通しさらに、アンバーライトIRA401を充填し
たカラムに通して、シアル酸をこの樹脂に吸着させた。
その後、水200lをアンバーライトIRA401の樹脂に通し、
夾雑物を流出させた。シアル酸の溶出は、実施例３と同
様に行い凍結乾燥後シアル酸36g（収率,0.18％）を得
た。Ｎ−アセチルノイラミン酸の純度はチオバルビツー
ル酸法による測定で約97％であった。Example 5 20 kg of defatted egg yolk L was suspended in 150 l of water, then adjusted to pH 1.4 by adding 6N sulfuric acid, and acid hydrolyzed at 80 ° C. for 60 minutes with gentle stirring. After hydrolysis, lime milk [CaCO 3 : Ca (OH)
2 = 1: 1] was added to adjust the pH to 5.0. After removing the insoluble matter with a pressurizer, it was passed through a column filled with Amberlite IR-116 and further passed through a column filled with Amberlite IRA401 to adsorb sialic acid onto this resin.
Then, pass 200 l of water through the resin of Amberlite IRA401,
Contaminants were drained. Elution of sialic acid was carried out in the same manner as in Example 3, and after freeze-drying, 36 g of sialic acid (yield, 0.18%) was obtained. The purity of N-acetylneuraminic acid was about 97% as measured by the thiobarbituric acid method.
本発明により、従来困難であったシアル酸を大量にしか
も安価に製造供給することが可能となった。さらに、卵
黄油の製造と組合せることにより卵黄のより有効な利用
が企れ、産業上多大な貢献をするものである。According to the present invention, it has become possible to manufacture and supply a large amount of sialic acid, which was difficult in the past, at low cost. Furthermore, by combining with the production of egg yolk oil, more effective use of egg yolk is attempted, which makes a great contribution to the industry.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 金 武▲祚▼ 三重県四日市市赤堀新町９番５号 太陽化 学株式会社内 (72)発明者 山崎 長孝 三重県四日市市赤堀新町９番５号 太陽化 学株式会社内 審査官 横尾 俊一 (56)参考文献 特開 平２−69492（ＪＰ，Ａ) 日本畜産学会報，第61巻３号277−282頁 （1990) ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Takeshi Kim ▲ 祚 ▼ 9-5 Akahorishinmachi, Yokkaichi-shi, Mie Prefecture Solar Chemistry Co., Ltd. (72) Nagataka Yamazaki 9-5 Akahorishinmachi, Yokkaichi-shi, Mie Prefecture No. Taiyo Kagaku Co., Ltd. Examiner Shunichi Yokoo (56) References JP-A-2-69492 (JP, A) Bulletin of the Japan Society of Animal Science, Vol. 61, No. 3, pp. 277-282 (1990)
Claims (1)
シアル酸の製造法。1. A method for producing sialic acid, which comprises hydrolyzing defatted egg yolk.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2235434A JPH06102672B2 (en) | 1990-09-04 | 1990-09-04 | Method for producing sialic acid |
| IL99245A IL99245A0 (en) | 1990-09-04 | 1991-08-20 | Method for production of sialic acid |
| DE69122936T DE69122936T2 (en) | 1990-09-04 | 1991-08-22 | Process for the production of sialic acid |
| US07/748,560 US5233033A (en) | 1990-09-04 | 1991-08-22 | Method for production of sialic acid |
| EP91307753A EP0474410B1 (en) | 1990-09-04 | 1991-08-22 | Method for production of sialic acid |
| CA002050125A CA2050125A1 (en) | 1990-09-04 | 1991-08-29 | Method for production of sialic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2235434A JPH06102672B2 (en) | 1990-09-04 | 1990-09-04 | Method for producing sialic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04117393A JPH04117393A (en) | 1992-04-17 |
| JPH06102672B2 true JPH06102672B2 (en) | 1994-12-14 |
Family
ID=16986054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2235434A Expired - Fee Related JPH06102672B2 (en) | 1990-09-04 | 1990-09-04 | Method for producing sialic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06102672B2 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0899988A (en) * | 1994-09-29 | 1996-04-16 | Takehiko Yamamoto | Production of oligosaccharide containing sialic acids |
| JPH08266255A (en) * | 1995-03-30 | 1996-10-15 | Taiyo Kagaku Co Ltd | Learning ability improving composition |
| US5772999A (en) * | 1996-07-30 | 1998-06-30 | Dcv Biologics, L.P. | Method of preventing, countering, or reducing NSAID-induced gastrointestinal damage by administering milk or egg products from hyperimmunized animals |
| KR100386424B1 (en) * | 2000-01-10 | 2003-06-02 | 주식회사 두산 | Process For Preparing Oligosaccharide Containing Sialic Acid |
| CN117137090B (en) * | 2023-08-25 | 2024-07-12 | 广州菲勒生物科技有限公司 | Hydrolyzed yolk powder compound and preparation method thereof |
| CN119791286A (en) * | 2025-03-14 | 2025-04-11 | 山东隆贝生物科技有限公司 | N-acetylneuraminic acid tablet and preparation method thereof |
-
1990
- 1990-09-04 JP JP2235434A patent/JPH06102672B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| 日本畜産学会報，第６１巻３号２７７−２８２頁（１９９０） |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04117393A (en) | 1992-04-17 |
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