JPH0269192A - Production of glycoside using enzyme - Google Patents
Production of glycoside using enzymeInfo
- Publication number
- JPH0269192A JPH0269192A JP21978588A JP21978588A JPH0269192A JP H0269192 A JPH0269192 A JP H0269192A JP 21978588 A JP21978588 A JP 21978588A JP 21978588 A JP21978588 A JP 21978588A JP H0269192 A JPH0269192 A JP H0269192A
- Authority
- JP
- Japan
- Prior art keywords
- sugar
- organic solvent
- galactose
- galactosidase
- glycoside
- 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
- 229930182470 glycoside Natural products 0.000 title claims abstract description 14
- 150000002338 glycosides Chemical class 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 102000004190 Enzymes Human genes 0.000 title description 7
- 108090000790 Enzymes Proteins 0.000 title description 7
- 235000000346 sugar Nutrition 0.000 claims abstract description 18
- 229930182830 galactose Natural products 0.000 claims abstract description 13
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- 102000005936 beta-Galactosidase Human genes 0.000 claims abstract description 10
- 108010005774 beta-Galactosidase Proteins 0.000 claims abstract description 10
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 150000001720 carbohydrates Chemical class 0.000 claims description 3
- 150000008163 sugars Chemical class 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 15
- -1 aliphatic alcohols Chemical class 0.000 abstract description 10
- 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 abstract description 6
- 239000008101 lactose Substances 0.000 abstract description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 5
- 240000006439 Aspergillus oryzae Species 0.000 abstract description 5
- 235000002247 Aspergillus oryzae Nutrition 0.000 abstract description 5
- 239000000243 solution Substances 0.000 abstract description 4
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 abstract description 3
- 150000002016 disaccharides Chemical class 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 abstract description 2
- 229930182478 glucoside Natural products 0.000 abstract 1
- 150000008131 glucosides Chemical class 0.000 abstract 1
- 150000004676 glycans Chemical class 0.000 abstract 1
- 230000002779 inactivation Effects 0.000 abstract 1
- 230000001766 physiological effect Effects 0.000 abstract 1
- 229920001282 polysaccharide Polymers 0.000 abstract 1
- 239000005017 polysaccharide Substances 0.000 abstract 1
- 230000007704 transition Effects 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 150000002772 monosaccharides Chemical class 0.000 description 4
- 239000008057 potassium phosphate buffer Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000000975 bioactive effect Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 239000008055 phosphate buffer solution Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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
- 229920000936 Agarose Polymers 0.000 description 1
- 102000005744 Glycoside Hydrolases Human genes 0.000 description 1
- 108010031186 Glycoside Hydrolases Proteins 0.000 description 1
- PNIWLNAGKUGXDO-UHFFFAOYSA-N Lactosamine Natural products OC1C(N)C(O)OC(CO)C1OC1C(O)C(O)C(O)C(CO)O1 PNIWLNAGKUGXDO-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- AXQLFFDZXPOFPO-UHFFFAOYSA-N UNPD216 Natural products O1C(CO)C(O)C(OC2C(C(O)C(O)C(CO)O2)O)C(NC(=O)C)C1OC(C1O)C(O)C(CO)OC1OC1C(O)C(O)C(O)OC1CO AXQLFFDZXPOFPO-UHFFFAOYSA-N 0.000 description 1
- AXQLFFDZXPOFPO-UNTPKZLMSA-N beta-D-Galp-(1->3)-beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->4)-beta-D-Glcp Chemical compound O([C@@H]1O[C@H](CO)[C@H](O)[C@@H]([C@H]1O)O[C@H]1[C@@H]([C@H]([C@H](O)[C@@H](CO)O1)O[C@H]1[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O1)O)NC(=O)C)[C@H]1[C@H](O)[C@@H](O)[C@H](O)O[C@@H]1CO AXQLFFDZXPOFPO-UNTPKZLMSA-N 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- USIPEGYTBGEPJN-UHFFFAOYSA-N lacto-N-tetraose Natural products O1C(CO)C(O)C(OC2C(C(O)C(O)C(CO)O2)O)C(NC(=O)C)C1OC1C(O)C(CO)OC(OC(C(O)CO)C(O)C(O)C=O)C1O USIPEGYTBGEPJN-UHFFFAOYSA-N 0.000 description 1
- DOVBXGDYENZJBJ-ONMPCKGSSA-N lactosamine Chemical compound O=C[C@H](N)[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O DOVBXGDYENZJBJ-ONMPCKGSSA-N 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 230000006098 transglycosylation Effects 0.000 description 1
- 238000005918 transglycosylation reaction Methods 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は酵素による有用な界面活性能および生理活性能
を有するグリコシドの製造に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to the production of glycosides having useful surfactant and bioactive abilities using enzymes.
（従来の技術およびその問題点）
配糖体系界面活性剤としてアルキルサツカライド類が知
られているが、このアルキルサツカライドの機能として
高気泡性、高洗浄性、高泡安定性、低刺激性、高生分解
性などが上げられ注目されている。(Prior art and its problems) Alkyl saccharides are known as glycoside surfactants, but the functions of these alkyl saccharides include high foaming properties, high detergency, high foam stability, and low irritation. It is attracting attention due to its high biodegradability.
しかし、これらアルキルサツカライド類の化学合成法に
よる製造においては、反応選択性が低いこと、反応が多
段階であること、副生物を与える場合が多いことなどの
問題点があり、得られた生成物を製品に配合する場合そ
の製品の品質に大きな影響を及ぼす可能性がある。However, the production of these alkyl saccharides by chemical synthesis methods has problems such as low reaction selectivity, multi-step reactions, and often by-products. When a substance is added to a product, it may have a significant impact on the quality of the product.
一方酵素合成法では、反応が選択的に行われること、反
応が１段階であること、副生成物が少ないことなどの利
点がある。このような酵素合成法は種々検討されており
、例えば、糖供与体としてアリールグリコシドを用い、
有機溶媒水溶液中でグリコシターゼのトランスグリコシ
デーシランを利用する方法が提案されている（特公昭５
９−２８４００）、 Ｌかし、アリールグリコシドを糖
供与体として用いた場合子り−ルグリコシドが工業的生
産レベルでのコストが非常に高くなること、及びアリー
ルグリコシドが物性的に不安定で分解し易いことなどの
難点がある。On the other hand, the enzymatic synthesis method has advantages such as selective reaction, one-step reaction, and fewer by-products. Various such enzymatic synthesis methods have been studied, for example, using aryl glycosides as sugar donors,
A method using transglycoside silane of glycosidase in an aqueous solution of an organic solvent has been proposed (Japanese Patent Publication No. 5
9-28400), when aryl glycosides are used as sugar donors, the cost at an industrial production level is extremely high, and aryl glycosides are physically unstable and decompose. There are some drawbacks, such as being easy.
（問題点を解決するための手段）
したがって、本発明は有用な界面活性能および生理活性
能を有するグリコシドを水系および／または有機溶媒水
溶液系で酵素により製造する方法を提供することを目的
とする。(Means for Solving the Problems) Therefore, an object of the present invention is to provide a method for producing a glycoside having useful surfactant and bioactive abilities using an enzyme in an aqueous system and/or an aqueous organic solvent system. .
本発明者らは、上述した状況に鑑み酵素を利用したグリ
コシドの合成を鋭意研究した結果、酵素を用い糖供与体
として単糖および／または２糖以上のＩＪ！類を用いる
ことにより本発明を完成するに至った。In view of the above-mentioned situation, the present inventors have conducted extensive research into the synthesis of glycosides using enzymes, and have found that monosaccharide and/or disaccharide or more IJ! The present invention was completed by using the following.
即ち本発明はガラクトース又は２糖以上の糖類で非還元
性末端にガラクトースを含む糖類を糖供与体とし、直鎖
、分岐または脂肪族のアルコール類を糖受容体として、
水系および／または有機溶媒水溶液系においてβ−ガラ
クトシダーゼを用いて反応させてグリコシドを得ること
を特徴とするグリコシドの製造方法を提供するものであ
る。That is, the present invention uses galactose or a disaccharide or more saccharide containing galactose at its non-reducing end as a sugar donor, and uses a linear, branched or aliphatic alcohol as a sugar acceptor.
The present invention provides a method for producing glycosides, which is characterized in that the glycosides are obtained by reaction using β-galactosidase in an aqueous system and/or an aqueous organic solvent system.
本発明において非還元性末端とは多ｗｉ分子において、
その構成単糖の還元基が遊離していない方の末端をいう
。In the present invention, a non-reducing end refers to a multi-wi molecule,
It refers to the end of the constituent monosaccharide whose reducing group is not free.
以下に本発明の詳細な説明する。The present invention will be explained in detail below.
本発明では水系および／または有機溶媒水溶液系におい
て酵素を使用することによりグリコシドを製造すること
ができる。本発明に於て糖供与体として用いられる非還
元末端にガラクトースを含む糖類としては次の様なもの
がある。In the present invention, glycosides can be produced by using enzymes in an aqueous system and/or an aqueous organic solvent system. Examples of sugars containing galactose at the non-reducing end that can be used as sugar donors in the present invention include the following.
単糖・・・ガラクトース
２糖・・・ラクトース、カラビオース、ラクトサミンな
ど
３ｔ！以上・・・ノイラミンラクトース、ラクト−Ｎテ
トラオース、アガロース、ガラ
クタン、カラーギーナン
また、糖受容体として用いるアルコール類は第１級、第
２級、第３級アルコールおよび２価以上のアルコール類
である。例えば、メタノール、エタノール、ｎ−プロパ
ツール、イソプロパツール、オクタツール、ｎ−デカノ
ール、シクロヘキサノール、グリセロール、ベンジルア
ルコールなどが挙げられる。Monosaccharides: Galactose Disaccharides: 3 tons of lactose, carabiose, lactosamine, etc.! Above...neuramin lactose, lacto-N-tetraose, agarose, galactan, carrageenan, and alcohols used as sugar acceptors include primary, secondary, tertiary alcohols, and dihydric or higher alcohols. Examples include methanol, ethanol, n-propanol, isopropanol, octatool, n-decanol, cyclohexanol, glycerol, benzyl alcohol, and the like.
本発明に用いる酵素であるβ−ガラクトシダーゼは、有
機溶媒中で完全に失活しない物であれば如何なる起源の
ものでもよいが糖転移活性の高いものが好ましくアスペ
ルギルスオリザエ（Ａｓｐｅｒｇｉｌｌｕｓ ｏｒｙｚ
ａｅ）、タルイベロマイセスラクチス（Ｋｌｕｙｖｅｒ
ｏｍｙｃｅｓ １ａｃｔｉｓ）などを起源とするβ−ガ
ラクトシダーゼなどが挙げられる。The enzyme β-galactosidase used in the present invention may be of any origin as long as it is not completely inactivated in an organic solvent, but those with high transglycosylation activity are preferred.
ae), Thaluberomyces lactis (Kluyver)
Examples include β-galactosidase originating from S. omyces 1actis).
本発明において、糖供与体、すなわち単糖以上のＩＩ類
が非還元末端にガラクトースを含む糖類と、糖受容体で
あるアルコール類との反応割合は１ｉｌｌｌ ｍｏｌに
対しアルコール［１ｍｏ１以上、望ましくは、１：５−
１：５０である。In the present invention, the reaction ratio of the sugar donor, i.e., a monosaccharide or higher Class II saccharide containing galactose at the non-reducing end, and the sugar acceptor, alcohol, is 1 mol to 1 mol of alcohol [1 mol or more, preferably, 1:5-
It was 1:50.
本発明の反応に於て有機溶媒水溶液系に使用できる有機
溶媒としては、アセトニトリル、アセトン、ジオキサン
、ジメチルスルホキシド、ジメチルホルムアミド、酢酸
エチル、四塩化炭素、ベンゼン、クロロホルム、ヘキサ
ンなどがある。Examples of organic solvents that can be used in the organic solvent aqueous solution system in the reaction of the present invention include acetonitrile, acetone, dioxane, dimethyl sulfoxide, dimethyl formamide, ethyl acetate, carbon tetrachloride, benzene, chloroform, and hexane.
反応は反応系に糖が溶解するのに必要な水分の存在下で
行なうのが望ましい。水分は全反応系に対して１０〜７
０％、好ましくは２０〜５５％程度がよい。The reaction is preferably carried out in the presence of water necessary for dissolving the sugar in the reaction system. Water content is 10 to 7 for the entire reaction system.
0%, preferably about 20 to 55%.
また、反応ｐＨは通常３−９の間で選択すれば良いが、
アスペルギルスオリザエのβ−ガラクトシダーゼを使用
する場合は、ｐｕｓ、ｏ付近で反応させるのが望ましい
。反応時間は、通常３−５００分であり、反応温度は５
−７０″Ｃである。In addition, the reaction pH can usually be selected between 3-9,
When Aspergillus oryzae β-galactosidase is used, it is desirable to carry out the reaction near pus and o. The reaction time is usually 3-500 minutes, and the reaction temperature is 5
-70″C.
（実施例） 以下、本発明を実施例により具体的に説明する。(Example) Hereinafter, the present invention will be specifically explained with reference to Examples.
実施例１
〔ラクトースとシクロヘキサノールよりシクロへキシル
−β−Ｄ−ガラクトシドの合成〕ラクトース１．８０
ｇ （５ｍｍｏｌ）を０．Ｉｎリン酸カリウム緩衝液（
ｐＨ５，０）１１−に溶解し、これにシクロヘキサノー
ル１５．０ ｇとアセトニトリル１０．０ｇを加え、上
記リン酸緩衝液１−にアスペルギルスオリザエ由来のβ
−ガラクトシダーゼ（シグマ社製）２０■（１０６０）
を溶解したものを加え、撹拌し、３０°Ｃで３時間反応
させた。これに、メタノールを２０ｍ１加え酵素を沈澱
させ遠心分離し液層を凍結乾燥させ、トリメチルシリル
化し、ガスクロマトグラフィーおよびＧＣ−ＭＡＳによ
りシクロへキシル−β−〇−ガラクトシドの生成を確認
した。Example 1 [Synthesis of cyclohexyl-β-D-galactoside from lactose and cyclohexanol] Lactose 1.80
g (5 mmol) to 0. In potassium phosphate buffer (
15.0 g of cyclohexanol and 10.0 g of acetonitrile were added to the solution, and β from Aspergillus oryzae was added to the above phosphate buffer solution 1-.
-Galactosidase (manufactured by Sigma) 20■ (1060)
A dissolved solution was added, stirred, and reacted at 30°C for 3 hours. To this, 20 ml of methanol was added to precipitate the enzyme, centrifuged, the liquid layer was freeze-dried, trimethylsilylated, and the production of cyclohexyl-β-〇-galactoside was confirmed by gas chromatography and GC-MAS.
実施例２
〔ラクトースとｎ−デシルアルコールより ｎ−デシル
−β−Ｄ−ガラクトシドの合成〕ラクトース１．８０
ｇ （５ｍａ＋ｏｌ）を０．１とリン酸カリウム緩衝液
（ｐＨ５，０）３６ｒａ１に溶解し、これにｎ−デシル
アルコール２３．７ｇとアセトニトリル１０．０ ｇを
加え、上記リン酸緩衝液０．１ ｒｎｌにアスペルギル
スオリザエ由来のβ−ガラクトシダーゼ２０■（１０６
０）を溶解したものを加え激しく撹拌し、３０°Ｃで２
００時間反応せた。これに、酢酸エチル５０１１７と水
４０−を加えよく混合し、静置後玉層を分取し、有機溶
媒をトッピングし、得られた固形物をクロロホルム−メ
タノールの８：２の混合溶媒にてシリカゲルカラムにか
け、ｎ−デシル−β−Ｄ−ガラクトシド相当分画を得た
。これをロータリーエバポレーターにかけ溶媒を留去し
て得られた固形物をトリメチルシリル化し、ガスクロマ
トグラフィー及びＧＣ−ＭＡＳにかけｎ−デシル−β−
Ｄ−ガラクトシドの生成を確認した。得られた生成物は
０．１ ｇであり、モル収率５．６％であった。Example 2 [Synthesis of n-decyl-β-D-galactoside from lactose and n-decyl alcohol] Lactose 1.80
Dissolve 0.1g (5ma+ol) in 36ra1 of potassium phosphate buffer (pH 5,0), add 23.7g of n-decyl alcohol and 10.0g of acetonitrile, and dissolve 0.1g of the above phosphate buffer. β-galactosidase 20 (106) derived from Aspergillus oryzae in rnl
0) was added, stirred vigorously, and heated at 30°C for 2 hours.
The reaction was carried out for 00 hours. To this, 50117 ethyl acetate and 40% water were added and mixed well. After standing still, the bead layer was collected, topped with an organic solvent, and the obtained solid was dissolved in a mixed solvent of chloroform and methanol at a ratio of 8:2. A silica gel column was applied to obtain a fraction corresponding to n-decyl-β-D-galactoside. This was applied to a rotary evaporator to remove the solvent, and the resulting solid was trimethylsilylated and subjected to gas chromatography and GC-MAS to n-decyl-β-
Production of D-galactoside was confirmed. The product obtained was 0.1 g, with a molar yield of 5.6%.
実施例３
〔ガラクトースとシクロヘキサノールよりシクロへキシ
ル−β−Ｄ−ガラクトシドの合成〕ガラクトース０．９
０ ｇ （５１１ｍｏｌ） を０．ＩＨリン酸カリウム
緩衝液（ｐＨ５，０）１１−に溶解し、これにシクロヘ
キサノール１５．０ ｇとアセトニトリルＩＱ、Ｏｇを
加え、上記リン酸緩衝液１＠ｌにアスペルギルスオリザ
エ由来のβ−ガラクトシダーゼ２０■（１０６１１）を
溶解したものを加え、撹拌し、３０°Ｃで３時間反応さ
せた。これに、メタノールを２０−加え、酵素を沈澱さ
せ、遠心分離し、液層を凍結乾燥させ、トリメチルシリ
ル化しガスクロマトグラフィーおよびＧＣ−ＭＡＳによ
りシクロへキシル−β−Ｄ−ガラクトシドの生成を確認
した。Example 3 [Synthesis of cyclohexyl-β-D-galactoside from galactose and cyclohexanol] Galactose 0.9
0 g (511 mol) to 0. Dissolve in IH potassium phosphate buffer (pH 5,0) 11-, add 15.0 g of cyclohexanol and acetonitrile IQ, Og, and add β-galactosidase derived from Aspergillus oryzae to the above phosphate buffer 1@l. A solution of 20■ (10611) was added, stirred, and reacted at 30°C for 3 hours. To this, methanol was added for 20 minutes to precipitate the enzyme, centrifugation was performed, the liquid layer was freeze-dried, trimethylsilylated, and the production of cyclohexyl-β-D-galactoside was confirmed by gas chromatography and GC-MAS.
実施例４
〔ガラクトースとれ一デシルアルコールより ｎ−デシ
ル−β−Ｄ−ガラクトシドの合成〕ガラクトース０．９
０ ｇ （５ｎ５ｏｌ）を０．１Ｍリン酸カリウム緩衝
液（ｐＨ５，０）３６ｍｊに溶解し、これにｎ−デシル
アルコール２３．７ ｇとアセトニトリル１０．０ ｇ
を加え、上記リン酸緩衝液０．１ ＠１にアスペルギル
スオリザエ由来のβ−ガラクトシダーゼ２０■（１０６
１１）を溶解したものを加え、３０°Ｃで２００時間反
応せた。これに、酢酸エチル５０ｍ７と水４０＠Ｉを加
えよく混合し、静置後玉層を分取し、有機溶媒をトッピ
ングし得られた固形物をクロロホルム−メタノールの８
：２の混合溶媒にてシリカゲルカラムにかけｎ−デシル
−β−Ｄ−ガラクトシド相当分画をロータリーエバポレ
ーターにかけ、溶媒を留去した。得られた固形物をトリ
メチルシリル化しガスクロマトグラフィーおよびＧＣ−
ＭＡＳにかけｎ−デシル−β−Ｄ−ガラクトシドの生成
を確認した。Example 4 [Synthesis of n-decyl-β-D-galactoside from galactose and monodecyl alcohol] Galactose 0.9
0 g (5n5ol) was dissolved in 36mj of 0.1M potassium phosphate buffer (pH 5,0), and to this was added 23.7 g of n-decyl alcohol and 10.0 g of acetonitrile.
was added to the above phosphate buffer solution 0.1@1 and β-galactosidase 20μ (106
11) was added and reacted at 30°C for 200 hours. To this, 50 m7 of ethyl acetate and 40 m7 of water were added and mixed well. After standing, the bead layer was taken out, and the solid material was topped with an organic solvent and dissolved in chloroform-methanol.
: A mixed solvent of 2 was applied to a silica gel column, and the fraction corresponding to n-decyl-β-D-galactoside was applied to a rotary evaporator, and the solvent was distilled off. The obtained solid was trimethylsilylated and subjected to gas chromatography and GC-
The production of n-decyl-β-D-galactoside was confirmed by MAS.
Claims (1)
クトースを含む糖類を糖供与体とし、直鎖、分岐または
脂肪族のアルコール類を糖受容体として、水系および／
または有機溶媒水溶液系においてβ−ガラクトシダーゼ
を用いて反応させてグリコシドを得ることを特徴とする
グリコシドの製造方法。Galactose or a saccharide of two or more sugars containing galactose at the non-reducing end is used as the sugar donor, and a straight chain, branched or aliphatic alcohol is used as the sugar acceptor.
Alternatively, a method for producing a glycoside, which is characterized in that a glycoside is obtained by reaction using β-galactosidase in an organic solvent aqueous solution system.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21978588A JPH0269192A (en) | 1988-09-02 | 1988-09-02 | Production of glycoside using enzyme |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21978588A JPH0269192A (en) | 1988-09-02 | 1988-09-02 | Production of glycoside using enzyme |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0269192A true JPH0269192A (en) | 1990-03-08 |
Family
ID=16740973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21978588A Pending JPH0269192A (en) | 1988-09-02 | 1988-09-02 | Production of glycoside using enzyme |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0269192A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001014575A1 (en) * | 1999-08-19 | 2001-03-01 | Showa Sangyo Co., Ltd. | Process for producing glycosides |
| JP2007176893A (en) * | 2005-12-28 | 2007-07-12 | Kao Corp | Method for producing alkylgalactoside |
-
1988
- 1988-09-02 JP JP21978588A patent/JPH0269192A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001014575A1 (en) * | 1999-08-19 | 2001-03-01 | Showa Sangyo Co., Ltd. | Process for producing glycosides |
| US6797496B1 (en) | 1999-08-19 | 2004-09-28 | Showa Sangyo Co., Ltd. | Process for producing glycosides |
| JP4504607B2 (en) * | 1999-08-19 | 2010-07-14 | 焼津水産化学工業株式会社 | Method for producing glycoside |
| JP2007176893A (en) * | 2005-12-28 | 2007-07-12 | Kao Corp | Method for producing alkylgalactoside |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69526182T2 (en) | Process for the preparation of trehalose derivatives | |
| EA028927B1 (en) | Method of producing a composition containing galacto-oligosaccharides | |
| KR20000045694A (en) | Method for producing 20(s)-ginsenoside rh2 | |
| JPH0269192A (en) | Production of glycoside using enzyme | |
| Apparu et al. | Chemoenzymatic synthesis of 6ω-S-α-d-glucopyranosyl-6ω-thiomaltooligosaccharides: their binding to Aspergillus niger glucoamylase G1 and its starch-binding domain | |
| KR100186757B1 (en) | Preparation process of 20(s)-ginsenocide rh1 and 20(s)-protopanaxtrlyol | |
| Freimund et al. | Enzymatic synthesis of D-glucosone 6-phosphate (D-arabino-hexos-2-ulose 6-(dihydrogen phosphate)) and NMR analysis of its isomeric forms | |
| US5612203A (en) | Process for producing saccharides | |
| Filice et al. | A chemo-biocatalytic approach in the synthesis of β-O-naphtylmethyl-N-peracetylated lactosamine | |
| JP4504607B2 (en) | Method for producing glycoside | |
| JP2750374B2 (en) | Novel production method of β-glucooligosaccharide by oxygen method | |
| JP3124356B2 (en) | Dextran production method | |
| KR19980027403A (en) | Method for preparing 20 (S) -ginsenoside Rg₂ | |
| Bonnet et al. | Oxidation of galactose and derivatives catalysed by galactose oxidase: structure and complete assignments of the NMR spectra of the main product | |
| JP2832746B2 (en) | Method for producing glycosphingolipid | |
| Hosaka et al. | Chemoenzymatic synthesis of sucuronic acid using d-glucurono-6, 3-lactone and sucrose as raw materials, and properties of the product | |
| JPH0670789A (en) | Production of glyceroglycolipid | |
| JP3045509B2 (en) | Method for producing mannose-containing oligosaccharides | |
| JP3200129B2 (en) | Method for producing α-glucosyl sugar compound | |
| US5403726A (en) | Enzymatic process for producing a galactosylβ1,3glycal disaccaride using β-galactosidase | |
| JP3916682B2 (en) | Method for producing glycoside | |
| JP3630378B2 (en) | Method for producing galactosylglycerols | |
| de Santiago et al. | Enzymatic synthesis of disaccharides by β-galactosidase-catalyzed glycosylation of a glycocluster | |
| Fujita et al. | Enzymatic preparation of specifically modified linear maltooligosaccharides through Taka-amylase A-catalyzed hydrolysis of 6-O-arenesulfonyl-. GAMMA.-cyclodextrins. | |
| JP2606854B2 (en) | Method for producing isoprimeverose |