JPH04121198A - Production of glucopyranosyl-1,6-sorbitol - Google Patents
Production of glucopyranosyl-1,6-sorbitolInfo
- Publication number
- JPH04121198A JPH04121198A JP24057290A JP24057290A JPH04121198A JP H04121198 A JPH04121198 A JP H04121198A JP 24057290 A JP24057290 A JP 24057290A JP 24057290 A JP24057290 A JP 24057290A JP H04121198 A JPH04121198 A JP H04121198A
- Authority
- JP
- Japan
- Prior art keywords
- sorbitol
- glucopyranosyl
- isomaltose
- enzyme
- mixture
- 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.)
- Pending
Links
- 239000000600 sorbitol Substances 0.000 title claims abstract description 52
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- AYRXSINWFIIFAE-SCLMCMATSA-N Isomaltose Natural products OC[C@H]1O[C@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)[C@@H](O)[C@@H](O)[C@@H]1O AYRXSINWFIIFAE-SCLMCMATSA-N 0.000 claims abstract description 24
- DLRVVLDZNNYCBX-RTPHMHGBSA-N isomaltose 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(O)O1 DLRVVLDZNNYCBX-RTPHMHGBSA-N 0.000 claims abstract description 23
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 108090000790 Enzymes Proteins 0.000 claims abstract description 13
- 102000004190 Enzymes Human genes 0.000 claims abstract description 13
- 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 claims abstract description 9
- 239000008103 glucose Substances 0.000 claims abstract description 9
- 238000006482 condensation reaction Methods 0.000 claims description 10
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 9
- 238000006722 reduction reaction Methods 0.000 claims description 7
- 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 claims description 5
- 238000010531 catalytic reduction reaction Methods 0.000 abstract description 3
- 235000013305 food Nutrition 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 238000000034 method Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002994 raw material Substances 0.000 description 7
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 150000002772 monosaccharides Chemical class 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- PVXPPJIGRGXGCY-TZLCEDOOSA-N 6-O-alpha-D-glucopyranosyl-D-fructofuranose 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(O)(CO)O1 PVXPPJIGRGXGCY-TZLCEDOOSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 238000006911 enzymatic reaction Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000005715 Fructose Substances 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 150000005846 sugar alcohols Chemical class 0.000 description 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- 108010073178 Glucan 1,4-alpha-Glucosidase Proteins 0.000 description 1
- 102100022624 Glucoamylase Human genes 0.000 description 1
- 108010056771 Glucosidases Proteins 0.000 description 1
- 102000004366 Glucosidases Human genes 0.000 description 1
- 102100024295 Maltase-glucoamylase Human genes 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 108010028144 alpha-Glucosidases Proteins 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000005640 glucopyranosyl group Chemical group 0.000 description 1
- 125000003153 isomaltose group Chemical group 0.000 description 1
- 239000000845 maltitol Substances 0.000 description 1
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 description 1
- 229940035436 maltitol Drugs 0.000 description 1
- 235000010449 maltitol Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 235000013615 non-nutritive sweetener Nutrition 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000005918 transglycosylation reaction Methods 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- 150000008501 α-D-glucopyranosides Chemical class 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、低カロリー甘味料等に有用なグルコピラノシ
ル−１，６−ソルビトールの製造法に関する。さらに詳
しくいえば、酵素の縮合反応により得られるグルコピラ
ノシル−１，６−ソルビトールとイソマルトースとを含
有する糖混合物から高純度のグルコピラノシル−１，６
−ソルビトールを製造する方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for producing glucopyranosyl-1,6-sorbitol, which is useful as a low-calorie sweetener. More specifically, highly purified glucopyranosyl-1,6-sorbitol and isomaltose are obtained by an enzymatic condensation reaction.
- Concerning a method for producing sorbitol.
［従来の技術およびその課題］
グルコピラノシル−１，６−ソルビトール（以下、ＧＳ
と略記することがある。）は、微生物により発酵されな
いこと、ショ糖の約４５％の甘味度を有すること、低カ
ロリーであることなど数多くの特徴を有する糖アルコー
ルであり、食品や医薬品の分野において有用な物質であ
る。[Prior art and its problems] Glucopyranosyl-1,6-sorbitol (hereinafter referred to as GS
It is sometimes abbreviated as. ) is a sugar alcohol that has many characteristics such as not being fermented by microorganisms, having a sweetness level of about 45% of sucrose, and being low in calories, and is a useful substance in the fields of food and medicine.
従来、グルコピラノシル−１，６−ソルビトールを製造
する方法としては、イソマルトースを水素添加する方法
（Ｊｏｕｒｎａｌ ｏｆ ｔｈｅ ＡｍｅｒｉｃａｎＳ
ｏｃｉｅｔｙ、 ７４．１０６２．（１９５２）） 、
イソマルツロース（α−Ｄ−グルコピラノシドー１．６
−フラクトース）をアルカリ水溶液中で水素添加する方
法が知られている（特公昭５６−３８５９９号）。Conventionally, as a method for producing glucopyranosyl-1,6-sorbitol, a method of hydrogenating isomaltose (Journal of the AmericanS
ociety, 74.1062. (1952)),
Isomaltulose (α-D-glucopyranoside 1.6
-Fructose) in an alkaline aqueous solution is known (Japanese Patent Publication No. 56-38599).
しかしながら、前者の方法では、出発原料として必要な
高純度イソマルトースが非常に高価であること、工業的
に利用できるイソマルトースにはマルトースが含まれて
おり、これを分離することは困難であり、これらを混合
した状態で還元処理するとＧＳとマルチトールとの混合
物となり、この混合物からＧＳのみを工業的に分離する
ことは困難である。However, in the former method, the high-purity isomaltose required as a starting material is very expensive, and the industrially available isomaltose contains maltose, which is difficult to separate. When a mixture of these is subjected to reduction treatment, a mixture of GS and maltitol is obtained, and it is difficult to industrially separate only GS from this mixture.
後者の方法では、９０％程度のＧＳを得ることができる
が、グルコピラノシル−１，６−マンニトール（ＧＭ）
が副生じ、このＧＭは工業的に分離が難しいこと、原料
のイソマルツロースは通常スクロース（ショ糖）の糖転
移反応で製造されるためイソマルツロースのほかにグル
コピラノシル−１，１−フラクトースをも生じ純度に問
題がある。In the latter method, about 90% GS can be obtained, but glucopyranosyl-1,6-mannitol (GM)
This GM is difficult to separate industrially, and the raw material isomaltulose is usually produced by transglycosylation reaction of sucrose, so glucopyranosyl-1,1-fructose is used in addition to isomaltulose. There is also a problem with purity.
また、分岐オリゴ糖を還元する方法があるが、五糖類以
上の糖アルコールが生成するため、ＧＳとの分離が困難
である。There is also a method of reducing branched oligosaccharides, but since sugar alcohols of pentasaccharides or higher are produced, it is difficult to separate them from GS.
また、安価な原料からＧＳを製造する方法として酵素の
縮合反応を利用する方法があるが、原料としてグルコー
スとソルビトールを共存させて縮合反応を行わせるため
、グルコースの濃度に依存してＧＳのほかにイソマルト
ースが生成する。従って、酵素法によるＧＳの製造法に
おいても、生成物はイソマルトースとの混合物となって
しまい、これを分離するのは難しい。In addition, there is a method of producing GS from inexpensive raw materials using an enzyme condensation reaction, but since the condensation reaction is carried out in the coexistence of glucose and sorbitol as raw materials, depending on the concentration of glucose, GS and other isomaltose is produced. Therefore, even in the enzymatic method for producing GS, the product is a mixture with isomaltose, which is difficult to separate.
以上の如く、従来の方法は、いずれもグルコピラノシル
−１，６−ソルビトールを工業的に高純度で製造するた
めの方法としては満足いくものとはいえない。As mentioned above, none of the conventional methods can be said to be satisfactory as a method for industrially producing glucopyranosyl-1,6-sorbitol with high purity.
従って、本発明の課題は、食品や医薬品の分野において
有用な物質であるグルコピラノシル−１゜６−ソルビト
ールを工業的に高純度で製造する方法を提供することに
ある。Therefore, an object of the present invention is to provide a method for industrially producing glucopyranosyl-1°6-sorbitol, which is a substance useful in the food and pharmaceutical fields, with high purity.
［課題を解決するための手段〕
本発明者らは、鋭意検討を重ねた結果、酵素の縮合反応
を利用したグルコピラノシル−１，６−ソルビトール合
成法の利点である安価な出発原料から効率よくグルコピ
ラノシル−１，６−ソルビトールを合成できるという特
徴を生かし、酵素の縮合反応終了液から、除蛋白をして
得られた未反応単糖類原料とＧＳとイソマルトースを含
有する三糖類とからなる糖混合物、あるいは各種カラム
クロマト法などで単糖類原料を取り除いたグルコピラノ
シル−１，６−ソルビトールとイソマルトースを含有す
る糖混合物を還元することにより容易に効率よくしかも
高純度にグルコピラノシル−１，６−ソルビトールを製
造することに成功し、本発明を完成するに至った。[Means for Solving the Problems] As a result of extensive studies, the present inventors have discovered that glucopyranosyl-1,6-sorbitol can be synthesized efficiently from inexpensive starting materials, which is an advantage of the glucopyranosyl-1,6-sorbitol synthesis method that utilizes an enzyme condensation reaction. - A sugar mixture consisting of an unreacted monosaccharide raw material obtained by deproteinizing the enzyme condensation reaction solution and a trisaccharide containing GS and isomaltose, taking advantage of its ability to synthesize 1,6-sorbitol. Alternatively, glucopyranosyl-1,6-sorbitol can be easily and efficiently and highly purified by reducing a sugar mixture containing glucopyranosyl-1,6-sorbitol and isomaltose from which monosaccharide raw materials have been removed using various column chromatography methods. They succeeded in manufacturing the product and completed the present invention.
すなわち、本発明は
１）酵素の存在下グルコースとソルビトールを共存させ
て縮合反応を行わせ、グルコピラノシル１．６−ソルビ
トールとイソマルトースの混合物へ変換し、次いで還元
反応によりイソマルトースをグルコピラノシル−１，６
−ソルビトールとすることを特徴とするグルコピラノシ
ル−１，６−ソルビトールの製造法を提供したものであ
る。That is, the present invention provides 1) a condensation reaction in which glucose and sorbitol coexist in the presence of an enzyme, converting the isomaltose into a mixture of glucopyranosyl-1,6-sorbitol and isomaltose, and then converting isomaltose into glucopyranosyl-1,6-sorbitol and isomaltose through a reduction reaction. 6
- Provides a method for producing glucopyranosyl-1,6-sorbitol, characterized in that it is converted into sorbitol.
本発明では、まずグルコースとソルビトールを出発原料
とし酵素の縮合反応を利用してグリコピラノシル−１，
６−ソルビトールとイソマルトースの混合物へ変換する
。In the present invention, first, glucose and sorbitol are used as starting materials, and glycopyranosyl-1,
Convert to a mixture of 6-sorbitol and isomaltose.
この酵素反応溶液における糖濃度範囲は特に制限はない
が、重量パーセント濃度で５〜１００％、望ましくは２
０〜１００％とすると、生成するグルコピラノシル−１
，６−ソルビトールとイソマルトースの量が増加する。The sugar concentration range in this enzyme reaction solution is not particularly limited, but the weight percent concentration is 5 to 100%, preferably 2.
When it is 0 to 100%, glucopyranosyl-1 produced
, 6-sorbitol and isomaltose levels increase.
反応に使用する酵素は、糖類の縮合反応作用を有するも
のであればその種類は特に限定されるものではないが、
α−グリコシダーゼ、グルコアミラーゼ等が例示される
。The type of enzyme used in the reaction is not particularly limited as long as it has a saccharide condensation reaction effect;
Examples include α-glycosidase and glucoamylase.
反応液に投入する酵素量は、その量が多いほど生成する
グルコピラノシル−１，６−ソルビトールとイソマルト
ースの量が増加する。The larger the amount of enzyme added to the reaction solution, the greater the amount of glucopyranosyl-1,6-sorbitol and isomaltose produced.
また、この酵素反応においては、ｐＨや温度等が重要な
要因となるが、使用する酵素が酵素活性を保っている範
囲内でｐＨ１温度および時間を設定すればよい。Further, in this enzyme reaction, pH, temperature, etc. are important factors, but the pH 1 temperature and time may be set within a range in which the enzyme used maintains its enzymatic activity.
本発明においては、酵素の縮合反応で生成したイソアル
ドースとグルコピラノシル−１，６−ソルビトールを含
有する糖混合物を還元する方法は、酵素を常法により除
去し、さらに未反応原料の単糖類（グルコースとソルビ
トール）を各種カラムクロマト法などで取り除いた後に
実施してもよいし、あるいは酵素の除去後、未反応原料
の単糖類を含有する状態で還元反応を実施してソルビト
ールとグルコピラノシル−１，６−ソルビトールの混合
物とした後、ソルビトールを各種カラムクロマト法など
で取り除いてもよい。In the present invention, the method for reducing the sugar mixture containing isoaldose and glucopyranosyl-1,6-sorbitol produced by the condensation reaction of the enzyme involves removing the enzyme by a conventional method, and further removing the unreacted raw material monosaccharide (glucopyranosyl-1,6-sorbitol). The reaction may be carried out after removing sorbitol and sorbitol by various column chromatography methods, or after removing the enzyme, a reduction reaction may be carried out in a state containing monosaccharides as unreacted raw materials to obtain sorbitol and glucopyranosyl-1,6. - After forming a mixture of sorbitol, sorbitol may be removed by various column chromatography methods.
還元の方法は特に限定されないが、例えば電解還元法お
よび高圧接触還元法を用いることができる。Although the reduction method is not particularly limited, for example, an electrolytic reduction method and a high-pressure catalytic reduction method can be used.
高圧接触還元法では、例えば次のような方法で還元を行
うことができる。In the high-pressure catalytic reduction method, reduction can be carried out, for example, by the following method.
ニッケル系または貴金属系などの触媒の存在化で水素添
加してイソマルトースからグルコピラノシル−１，６−
ソルビトールを生成させることができる。Glucopyranosyl-1,6- is converted from isomaltose by hydrogenation in the presence of a nickel-based or noble metal-based catalyst.
Sorbitol can be produced.
この水素添加の条件は、イソマルトースの分解が生じな
い条件であればどのような条件でもよい。The conditions for this hydrogenation may be any conditions as long as the decomposition of isomaltose does not occur.
通常は糖液の濃度を４０〜６０重量％にして、２０ｋｇ
／ｃＪ以上、更に好ましくは５０〜２００ｋｇ／Ｃ♂の
水素圧下で、１００〜１５０℃の温度下にて行うことが
好ましい。Usually, the concentration of sugar solution is 40 to 60% by weight, and 20 kg
It is preferable to carry out under a hydrogen pressure of /cJ or more, more preferably 50 to 200 kg/C♂, and a temperature of 100 to 150°C.
得られた水素添加液から触媒を除去したのち、必要に応
じ活性炭処理あるいはクロマト分離を行うことによって
、高純度グルコピラノシル−１゜６−ソルビトールを含
有する溶液を得ることができる。After removing the catalyst from the obtained hydrogenation solution, a solution containing highly purified glucopyranosyl-1°6-sorbitol can be obtained by performing activated carbon treatment or chromatographic separation as required.
この溶液は、濃縮してシラツブ状溶液とし、あるいは濃
縮乾燥機等を用いるなどして粉末状あるいは顆粒状のグ
ルコピラノシル−１，６−ソルビトール製品とすること
ができる。This solution can be concentrated into a slag-like solution, or can be made into a powder or granular glucopyranosyl-1,6-sorbitol product by using a concentration dryer or the like.
［実施例］
以下、実施例により本発明をさらに説明するが、本発明
はこれらの例のみに限定されるものではない。[Examples] Hereinafter, the present invention will be further explained with reference to Examples, but the present invention is not limited only to these Examples.
実施例１
重量％濃度で３０％グルコースおよび３０％ソルビトー
ルからなる反応溶液を、予じめ４５℃に設定しておいた
恒温槽に入れ、次いでこの反応溶液にα−グルコシダー
ゼを蛋白濃度が５ｍｇ／ｍｌとなるように加えて反応を
開始させた。３日後、反応を終了させるために常法に従
って除蛋白し、生成したグルコピラノシル−１，６−ソ
ルビトールの量を高速液体クロマトグラフィーで測定し
たところ、重量％濃度で約１３％であり、またイソマル
トースの生成量は約５％であった。この反応終了液４ｋ
ｇに対しラネーニッケル４０ｇをオートクレーブに仕込
み、水素圧１００ｋｇ／ｃ♂、温度１２０℃で４時間、
水素添加を行った。得られた液から触媒を分離し、イオ
ン交換体を用いて脱イオン化した後、グルコピラノシル
−１，６−ソルビトールの生成量を高速液体クロマトグ
ラフィーで測定した結果、重量％濃度で約１８％のグル
コピラノシル−１，６−ソルビトールが生成していた。Example 1 A reaction solution consisting of 30% glucose and 30% sorbitol at a weight percent concentration was placed in a constant temperature bath preset at 45°C, and then α-glucosidase was added to the reaction solution at a protein concentration of 5 mg/glucosidase. ml to start the reaction. After 3 days, the protein was removed according to a conventional method to terminate the reaction, and the amount of glucopyranosyl-1,6-sorbitol produced was measured by high-performance liquid chromatography, and it was found to be about 13% by weight, and the amount of glucopyranosyl-1,6-sorbitol was about 13% by weight. The production amount was about 5%. This reaction completed liquid 4k
40g of Raney nickel per g was charged into an autoclave, and heated at a hydrogen pressure of 100kg/c♂ and a temperature of 120°C for 4 hours.
Hydrogenation was performed. After separating the catalyst from the obtained liquid and deionizing it using an ion exchanger, the amount of glucopyranosyl-1,6-sorbitol produced was measured by high-performance liquid chromatography. As a result, glucopyranosyl with a concentration of about 18% by weight was measured using high performance liquid chromatography. -1,6-Sorbitol was produced.
実施例２
実施例１と同じ条件で、酵素の縮合反応により、グルコ
ピラノシル−１，６−ソルビトール合成を行わせ、重量
％濃度で約１３％グルコピラノシル−１，６−ソルビト
ールおよび約５％イソマルトースを含有する反応終了液
を得た。この反応液を活性炭クロマトグラフィーにかけ
て単糖類であるグルコースとソルビトールとを取り除い
た後、グルコピラノシル−１，６−ソルビトールおよび
イソマルトースを含有する糖組成物を得た。この糖組成
物１ ｋｇに対しラネーニッケル５ｇをオートクレーブ
に仕込み、水素圧１００ｋｇ／ｃ♂、温度１２０℃で２
時間水素添加を行った。得られた液から触媒を分離した
後、高速液体クロマトグラフィーで生成物の分析を行っ
た結果、純度９９％以上のグルコピラノシル−１，６−
ソルビトールが生成していた。Example 2 Glucopyranosyl-1,6-sorbitol was synthesized by enzymatic condensation reaction under the same conditions as in Example 1, yielding approximately 13% glucopyranosyl-1,6-sorbitol and approximately 5% isomaltose in weight percent concentration. A reaction-completed liquid containing the following components was obtained. After the reaction solution was subjected to activated carbon chromatography to remove monosaccharides glucose and sorbitol, a sugar composition containing glucopyranosyl-1,6-sorbitol and isomaltose was obtained. For 1 kg of this sugar composition, 5 g of Raney nickel was charged into an autoclave, and the hydrogen pressure was 100 kg/c♂ and the temperature was 120°C.
Hydrogenation was carried out for an hour. After separating the catalyst from the resulting liquid, the product was analyzed by high-performance liquid chromatography, and the result was glucopyranosyl-1,6- with a purity of over 99%.
Sorbitol was produced.
特許出願人 昭和電工株式会社Patent applicant: Showa Denko Co., Ltd.
Claims (1)
合反応を行わせ、グルコピラノシル−１，６−ソルビト
ールとイソマルトースの混合物へ変換し、次いで還元反
応によりイソマルトースをグルコピラノシル−１，６−
ソルビトールとすることを特徴とするグルコピラノシル
−１，６−ソルビトールの製造法。A condensation reaction is carried out in the coexistence of glucose and sorbitol in the presence of an enzyme, converting it into a mixture of glucopyranosyl-1,6-sorbitol and isomaltose, and then a reduction reaction converts isomaltose into glucopyranosyl-1,6-
A method for producing glucopyranosyl-1,6-sorbitol, characterized in that it is converted into sorbitol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24057290A JPH04121198A (en) | 1990-09-11 | 1990-09-11 | Production of glucopyranosyl-1,6-sorbitol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24057290A JPH04121198A (en) | 1990-09-11 | 1990-09-11 | Production of glucopyranosyl-1,6-sorbitol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04121198A true JPH04121198A (en) | 1992-04-22 |
Family
ID=17061518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24057290A Pending JPH04121198A (en) | 1990-09-11 | 1990-09-11 | Production of glucopyranosyl-1,6-sorbitol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04121198A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2741349A1 (en) * | 1995-11-17 | 1997-05-23 | Roquette Freres | NEW PROCESS FOR THE MANUFACTURE OF PALATINITOL |
| FR2741348A1 (en) * | 1995-11-17 | 1997-05-23 | Roquette Freres | NEW PROCESS FOR THE MANUFACTURE OF PALATINITOL |
| WO2001048214A3 (en) * | 1999-12-24 | 2002-04-25 | Markwart Kunz | METHOD FOR PRODUCING 6-0-α-D-GLUCOPYRANOSYL-D-SORBITE |
-
1990
- 1990-09-11 JP JP24057290A patent/JPH04121198A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2741349A1 (en) * | 1995-11-17 | 1997-05-23 | Roquette Freres | NEW PROCESS FOR THE MANUFACTURE OF PALATINITOL |
| FR2741348A1 (en) * | 1995-11-17 | 1997-05-23 | Roquette Freres | NEW PROCESS FOR THE MANUFACTURE OF PALATINITOL |
| WO1997019094A3 (en) * | 1995-11-17 | 1997-06-19 | Roquette Freres | Novel method for making palatinitol |
| WO1997019093A3 (en) * | 1995-11-17 | 1997-06-19 | Roquette Freres | Novel method for making palatinitol |
| US5856469A (en) * | 1995-11-17 | 1999-01-05 | Roquette Freres | Method for producing palatinitol |
| US6204378B1 (en) | 1995-11-17 | 2001-03-20 | Roquette Freres | Method for producing palatinitol |
| WO2001048214A3 (en) * | 1999-12-24 | 2002-04-25 | Markwart Kunz | METHOD FOR PRODUCING 6-0-α-D-GLUCOPYRANOSYL-D-SORBITE |
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