JPH0512358B2 - - Google Patents
Info
- Publication number
- JPH0512358B2 JPH0512358B2 JP63177141A JP17714188A JPH0512358B2 JP H0512358 B2 JPH0512358 B2 JP H0512358B2 JP 63177141 A JP63177141 A JP 63177141A JP 17714188 A JP17714188 A JP 17714188A JP H0512358 B2 JPH0512358 B2 JP H0512358B2
- Authority
- JP
- Japan
- Prior art keywords
- xylulose
- xylose
- exchange resin
- anion exchange
- present
- 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
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 42
- ZAQJHHRNXZUBTE-WUJLRWPWSA-N D-xylulose Chemical compound OC[C@@H](O)[C@H](O)C(=O)CO ZAQJHHRNXZUBTE-WUJLRWPWSA-N 0.000 claims description 27
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 21
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 21
- 239000003957 anion exchange resin Substances 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 5
- 108090000769 Isomerases Proteins 0.000 claims description 5
- 102000004195 Isomerases Human genes 0.000 claims description 5
- 238000012856 packing Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 description 7
- 238000010828 elution Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 108010093096 Immobilized Enzymes Proteins 0.000 description 3
- 208000007976 Ketosis Diseases 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 150000002584 ketoses Chemical class 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 108700040099 Xylose isomerases Proteins 0.000 description 2
- 150000001323 aldoses Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 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 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- -1 and as a result Chemical compound 0.000 description 1
- 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 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 239000012609 strong anion exchange resin Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、亜硫酸イオン型アニオン交換樹脂を
用いて、キシロースより調製される異性化液から
キシルロースを効率良く分離取得することを特徴
とするキシルロースの工業的製造法に関する。Detailed Description of the Invention [Industrial Application Field] The present invention is directed to a xylulose product, which is characterized in that xylulose is efficiently separated and obtained from an isomerized solution prepared from xylose using a sulfite ion type anion exchange resin. Concerning industrial manufacturing methods.
キシルロースは五炭糖代謝の重要な一員であ
り、その生理的意義は大きい。また、甘味を有す
る物質としてもその利用が期待されるが、現在希
少でコストが高く、その大量製造法の開発が強く
望まれている。
Xylulose is an important member of pentose metabolism and has great physiological significance. It is also expected to be used as a sweet substance, but it is currently rare and expensive, and there is a strong desire to develop a method for its mass production.
このキシルロースの製造法の一例として、アル
ドースであるキシロースを異性化酵素により異性
化してケトースであるキシルロースする方法があ
るが、この方法では異性化後に混合液からアルド
ースとケトースを分離する技術が不可欠である。 One example of a method for producing xylulose is to convert xylulose, an aldose, into xylulose, a ketose, by isomerizing it with an isomerase, but this method requires a technology to separate aldose and ketose from the mixture after isomerization. be.
従来、アルドースとケトースの分離において、
工業的に行なわれている例としては、カルシウム
型カチオン交換樹脂を用いたグルコースとフラク
トースの分離のみである。 Conventionally, in the separation of aldose and ketose,
The only example that has been carried out industrially is the separation of glucose and fructose using a calcium-type cation exchange resin.
一方、イオン交換樹脂を用いたキシロースとキ
シルロースの工業的分離に関する報告はいまだに
なく、実験室規模での極微量の分離が報告されて
いる（B.Lindberg and K.N.Slessor：
Carbohyd.Res.，５（1967）286−291およびS.P.
Olivier and P.J.du Toit：Biotechnol.Bioeng.，
28（1986）684−699）ものの、キシルロース分離
後に多量に存在するキシロースの再利用が困難な
ものであつた。 On the other hand, there have been no reports on the industrial separation of xylose and xylulose using ion exchange resins, and only trace amounts of separation on a laboratory scale have been reported (B. Lindberg and KNSlessor:
Carbohyd.Res., 5 (1967) 286-291 and SP
Olivier and PJdu Toit: Biotechnol.Bioeng.
28 (1986) 684-699), however, it was difficult to recycle the large amount of xylose present after xylulose separation.
また、分離操作なしでキシルロースを調製した
例としてキシロース異性化液を濃縮し、エタノー
ル抽出してキシルロース高含有の混合液を調製し
たのち、残存キシロースをキシロース高資化性の
微生物により除去する方法（L.C.Chiang，H.Y.
Hsiao，P.P.Ueng and G.T.Tsao：Appl.
Environ.Microbiol.，42（1981）66−69）が報告
されているが、この方法は日数およびコストがか
かり過ぎる上に収率が低いため、その実用化は考
えられなかつた。 In addition, as an example of preparing xylulose without a separation operation, the method involves concentrating the xylose isomerized liquid, extracting it with ethanol to prepare a mixed liquid with a high xylulose content, and then removing the residual xylose using microorganisms that can highly assimilate xylose ( LCChiang，HY
Hsiao, PPUeng and GTTsao: Appl.
Environ.Microbiol., 42 (1981) 66-69), but this method takes too many days and costs and has a low yield, so its practical application was not considered.
上述のような従来技術においては、キシルロー
スを大量に、しかも安価に製造することが困難で
あり、かつ分離後のキシロースの再利用を考えた
場合非常に不利なものであつた。
In the conventional techniques as described above, it is difficult to produce xylulose in large quantities at low cost, and it is very disadvantageous when considering the reuse of xylose after separation.
本発明では、これらの欠点を克服してキシルロ
ースを大量に生産して安価となし、その食品用素
材あるいは医薬品用素材としての利用を可能とす
ることを目的とする。 The purpose of the present invention is to overcome these drawbacks, produce xylulose in large quantities at low cost, and enable its use as a food material or a pharmaceutical material.
そこで本発明者らは、キシロースに異性化酵素
を作用させて調製した異性化液より、亜硫酸イオ
ン型アニオン交換樹脂を充填剤としたカラムを用
い、さらにそのカラム温度を30℃以上に上げるこ
とにより、キシルロースを効率良く分離取得し、
かつ分離後のキシロースを効率良く再利用できる
ことを見いだし、本発明を完成した。
Therefore, the present inventors used a column containing a sulfite ion-type anion exchange resin as a packing material from an isomerized solution prepared by treating xylose with an isomerase, and further raised the column temperature to 30°C or higher. , to efficiently separate and obtain xylulose,
They also discovered that xylose after separation can be efficiently reused, and completed the present invention.
すなわち、本発明はキシロースに異性化酵素を
作用させて得られる異性化液から亜硫酸イオン型
アニオン交換樹脂を充填剤としたカラムを用いて
30℃以上のカラム温度において、キシルロースを
効率良く分離取得することを特徴とするキシルロ
ースの工業的製造法に関する。 That is, the present invention uses a column containing a sulfite ion type anion exchange resin as a packing material from an isomerized liquid obtained by treating xylose with an isomerase.
The present invention relates to an industrial method for producing xylulose, which is characterized by efficiently separating and obtaining xylulose at a column temperature of 30°C or higher.
本発明において、分離に供する異性化液は、キ
シロースを基質とし公知の固定化酵素を作用させ
て調製する。固定化酵素としては、キシロースイ
ソメラーゼを担体結合法等の既知の方法により固
定化した酵素を用いる。異性化液を作るにあたつ
ては、20〜70％濃度のキシロース溶液に上記固定
化酵素を５〜40mg／ml加え、40〜70℃で１〜10時
間反応させればよい。 In the present invention, the isomerized solution to be subjected to separation is prepared by using xylose as a substrate and acting on a known immobilized enzyme. As the immobilized enzyme, an enzyme in which xylose isomerase is immobilized by a known method such as a carrier binding method is used. To prepare the isomerization solution, 5 to 40 mg/ml of the above-mentioned immobilized enzyme may be added to a 20 to 70% concentration xylose solution, and the mixture may be reacted at 40 to 70°C for 1 to 10 hours.
本発明では、亜硫酸イオン型アニオン交換樹脂
を充填したカラムを用いて上記異性化液からキシ
ルロースを分離する。 In the present invention, xylulose is separated from the isomerized liquid using a column packed with a sulfite ion type anion exchange resin.
本発明で用いるアニオン交換樹脂としては特に
制限はないが、強アニオン交換樹脂のＩ型が好ま
しい。具体的には、亜硫酸イオン型イオン型アニ
オン交換樹脂Dowex1などをあげることができ
る。 Although there are no particular limitations on the anion exchange resin used in the present invention, type I strong anion exchange resins are preferred. Specifically, sulfite ion type ionic anion exchange resin Dowex 1 can be mentioned.
上記アニオン交換樹脂を充填したカラムに、前
記した異性化液を通液するにあたつては、カラム
温度を30℃以上、好ましくは45〜65℃とすること
が望ましい。カラム温度が30℃未満であると、キ
シロースが広範囲にわたつて溶出し、その回収再
利用が困難となる。 When passing the above-mentioned isomerized solution through the column filled with the above-mentioned anion exchange resin, it is desirable that the column temperature be 30°C or higher, preferably 45 to 65°C. If the column temperature is below 30°C, xylose will be eluted over a wide range, making it difficult to recover and reuse it.
上記のようにして、キシルロースを効率よく製
造することができる上に、キシロースの再利用も
可能である。 In the manner described above, not only can xylulose be efficiently produced, but also the xylose can be reused.
次に、実施例を以て本発明をさらに詳細に説明
する。
Next, the present invention will be explained in more detail with reference to Examples.
実施例 １
40％濃度のキシロース溶液を水酸基型のアニオ
ン交換樹脂（IRA−45）で中性化（PH７）したの
ち、異性化酵素の活性化剤である硫酸マグネシウ
ムを10mM添加し、さらに20mg／mlの固定化キシ
ロースイソメラーゼを加え、60℃で４時間反応さ
せて異性化液（固形分濃度40％、固形分中キシル
ロース23％、キシロース77％）を得た。Example 1 After neutralizing (PH7) a 40% concentration xylose solution with a hydroxyl type anion exchange resin (IRA-45), 10mM of magnesium sulfate, which is an activator of isomerase, was added, and an additional 20mg/ ml of immobilized xylose isomerase was added and reacted at 60°C for 4 hours to obtain an isomerized solution (solid content concentration 40%, xylulose 23%, xylose 77% in solid content).
次に、外套をもつた内径2.6cm、高さ100cmのカ
ラムに亜硫酸型アニオン交換樹脂Dowex1×８
（200〜400メツシユ）を充填したカラムを用意し、
外套の温度を60℃に保持しながら、上記異性化液
を供給し、続いて脱イオン水で溶出した。 Next, a sulfite-type anion exchange resin Dowex 1×8 was placed in a column with an inner diameter of 2.6 cm and a height of 100 cm.
Prepare a column packed with (200 to 400 mesh),
The above isomerization solution was fed while maintaining the temperature of the mantle at 60°C, followed by elution with deionized water.
その溶出結果を第１図に示す。第１図から分か
るように、異性化液は完全にキシルロースとキシ
ロースに分離され、その結果高性能液体クロマト
グラフイー（HPLC）および薄層クロマトグラフ
イー（TCL）による分析で単一を示すキシルロ
ースの純品を２ｇ以上得た。 The elution results are shown in FIG. As can be seen from Figure 1, the isomerized solution is completely separated into xylulose and xylose, and as a result, xylulose is single in analysis by high performance liquid chromatography (HPLC) and thin layer chromatography (TCL). More than 2g of pure product was obtained.
比較例 １
実施例１において、カラム温度を30℃以下とし
たこと以外は実施例１と同様に操作を行つた。そ
の溶出結果を第２図に示す。Comparative Example 1 The same procedure as in Example 1 was carried out except that the column temperature was 30° C. or lower. The elution results are shown in FIG.
第２図から分かるように、キシルロースとキシ
ロースが完全に分離しない上に、キシロースが広
範囲にわたつて溶出し、その回収再利用は実質的
に不可能であつた。 As can be seen from FIG. 2, xylulose and xylose were not completely separated, and xylose was eluted over a wide range, making it virtually impossible to recover and reuse it.
本発明によれば、これまで大量生産が困難であ
つたキシルロースを効率良く生産でき、かつ溶出
するキシロースの回収再利用も可能となり、大量
かつ安価にキシルロースを生産することができ
る。本発明により得られたキシルロースは、食品
および医薬品用素材としての広い利用が期待され
る。
According to the present invention, xylulose, which has hitherto been difficult to mass-produce, can be efficiently produced, and eluted xylose can be recovered and reused, making it possible to produce xylulose in large quantities and at low cost. The xylulose obtained by the present invention is expected to be widely used as a material for foods and medicines.
第１図は、実施例１における異性化液の溶出曲
線を示し、第２図は比較例１における異性化液の
溶出曲線を示す。
FIG. 1 shows the elution curve of the isomerized solution in Example 1, and FIG. 2 shows the elution curve of the isomerized solution in Comparative Example 1.
Claims (1)
る異性化液から亜硫酸イオン型アニオン交換樹脂
を充填剤としたカラムを用いて30℃以上のカラム
温度においてキシルロースを効率良く分離取得す
ることを特徴とするキシルロースの工業的製造
法。 ２ カラム温度が45℃ないし65℃である請求項１
記載のキシルロースの工業的製造法。[Claims] 1. Efficient separation and acquisition of xylulose from an isomerized solution obtained by the action of an isomerase on xylose at a column temperature of 30°C or higher using a column containing a sulfite ion type anion exchange resin as a packing material. An industrial method for producing xylulose, characterized by: 2. Claim 1, wherein the column temperature is between 45°C and 65°C.
Industrial method for producing xylulose as described.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63177141A JPH0228191A (en) | 1988-07-18 | 1988-07-18 | Industrial production of xylose |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63177141A JPH0228191A (en) | 1988-07-18 | 1988-07-18 | Industrial production of xylose |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0228191A JPH0228191A (en) | 1990-01-30 |
| JPH0512358B2 true JPH0512358B2 (en) | 1993-02-17 |
Family
ID=16025900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63177141A Granted JPH0228191A (en) | 1988-07-18 | 1988-07-18 | Industrial production of xylose |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0228191A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19646971C2 (en) * | 1996-11-14 | 1999-06-02 | Suedzucker Ag | Use of L-xylulose for the treatment of hyperglycemia |
| CA2796759C (en) * | 2010-04-19 | 2022-10-04 | The University Of Toledo | Aldose-ketose transformation for separation and/or chemical conversion of c6 and c5 sugars from biomass materials |
| CN103242421B (en) * | 2013-05-09 | 2015-04-15 | 北京化工大学 | Process method for co-producing diosgenin, glucose, xylose and arabinose by hydrolyzing yellow ginger by utilizing volatile acid |
-
1988
- 1988-07-18 JP JP63177141A patent/JPH0228191A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0228191A (en) | 1990-01-30 |
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