JP2716082B2 - Ribose selective transporter - Google Patents
Ribose selective transporterInfo
- Publication number
- JP2716082B2 JP2716082B2 JP22691495A JP22691495A JP2716082B2 JP 2716082 B2 JP2716082 B2 JP 2716082B2 JP 22691495 A JP22691495 A JP 22691495A JP 22691495 A JP22691495 A JP 22691495A JP 2716082 B2 JP2716082 B2 JP 2716082B2
- Authority
- JP
- Japan
- Prior art keywords
- solution
- ribose
- complex
- fat
- strontium
- 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
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 title claims description 66
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 title claims description 30
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 title claims description 30
- 229910052788 barium Inorganic materials 0.000 claims description 30
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 30
- 229910052712 strontium Inorganic materials 0.000 claims description 23
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 23
- -1 2-ethylhexyl group Chemical group 0.000 claims description 4
- 239000000243 solution Substances 0.000 description 74
- 230000032258 transport Effects 0.000 description 30
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 20
- 150000002772 monosaccharides Chemical class 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 8
- 229910001863 barium hydroxide Inorganic materials 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 6
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 6
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 4
- 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 4
- 239000011575 calcium Substances 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 description 3
- SHZGCJCMOBCMKK-SVZMEOIVSA-N D-fucopyranose Chemical compound C[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O SHZGCJCMOBCMKK-SVZMEOIVSA-N 0.000 description 3
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 3
- 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 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- PNNNRSAQSRJVSB-BXKVDMCESA-N aldehydo-L-rhamnose Chemical compound C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O PNNNRSAQSRJVSB-BXKVDMCESA-N 0.000 description 3
- 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 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- GQZXNSPRSGFJLY-UHFFFAOYSA-N hydroxyphosphanone Chemical compound OP=O GQZXNSPRSGFJLY-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XDIYNQZUNSSENW-UUBOPVPUSA-N (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O XDIYNQZUNSSENW-UUBOPVPUSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical group C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- SRBFZHDQGSBBOR-OWMBCFKOSA-N L-ribopyranose Chemical compound O[C@H]1COC(O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-OWMBCFKOSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229920005597 polymer membrane Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Description
【０００１】[0001]
【発明の属する技術分野】本発明はリボースの新規な選
択輸送剤に関するものである。さらに詳しくいえば、本
発明は、種々の単糖類が存在する水溶液から、リボース
を効率よく液膜を通して輸送する能力を有し、選択的か
つ連続的に抽出しうる安価な脂溶性バリウム又はストロ
ンチウム錯体から成るリボースの選択輸送剤に関するも
のである。TECHNICAL FIELD The present invention relates to a novel selective transporter of ribose. More specifically, the present invention provides an inexpensive fat-soluble barium or strontium complex capable of selectively and continuously extracting ribose from an aqueous solution containing various monosaccharides, which has the ability to efficiently transport ribose through a liquid membrane. Comprising a selective transport agent for ribose comprising:
【０００２】[0002]
【従来の技術】Ｄ−グルコースやＤ−リボースなどの単
糖類は自然界に広く分布しており、そして生化学製品と
して種々の用途に用いられている。特に、Ｄ−グルコー
ス（ブドウ糖）は医薬用、甘味剤、染色や皮なめしなど
の還元剤、分析用試薬などとして、Ｄ−リボースは、医
薬用や飼料添加剤として使用されているリボフラビン
（ビタミンＢ２）の原料などとして、需要が多く、これ
らは現在発酵法により工業生産されてる。2. Description of the Related Art Monosaccharides such as D-glucose and D-ribose are widely distributed in nature and are used for various purposes as biochemical products. In particular, D-glucose (glucose) is used as a pharmaceutical, a sweetener, a reducing agent such as dyeing and tanning, and an analytical reagent. D-ribose is used as a riboflavin (vitamin B2 ) Is in great demand as a raw material, and these are currently produced industrially by fermentation.
【０００３】ところで、多くの種類の単糖類を含有する
水溶液から、所望の単糖類を選択的に抽出することは、
高純度の単糖類を得る方法として、工業的に需要であ
る。そこで、本発明者らは、単糖類を選択的に抽出する
方法について鋭意研究を重ね、先に、水酸化カルシウム
又は塩化カルシウムとリン酸ジエステルから得られたク
ロロホルム可溶な錯体により、リボースが選択的に液膜
を通して輸送されることを見出した。しかしながら、こ
の場合の錯体は、リボースの輸送速度が遅く、必ずしも
工業的に有利なものとはいえない。By the way, to selectively extract a desired monosaccharide from an aqueous solution containing many types of monosaccharides,
As a method for obtaining high-purity monosaccharides, there is an industrial demand. Therefore, the present inventors have intensively studied a method for selectively extracting monosaccharides, and first, ribose was selected by a chloroform-soluble complex obtained from calcium hydroxide or calcium chloride and a phosphoric diester. Was found to be transported through the liquid membrane. However, the complex in this case has a low ribose transport rate, and is not necessarily industrially advantageous.
【０００４】[0004]
【発明が解決しようとする課題】本発明は、種々の単糖
類が存在する水溶液から、リボースを効率よくかつ選択
的に液膜を通して輸送する能力を有するリボースの選択
輸送剤を提供することをその課題とする。An object of the present invention is to provide a selective ribose transport agent capable of efficiently and selectively transporting ribose from an aqueous solution containing various monosaccharides through a liquid membrane. Make it an issue.
【０００５】[0005]
【課題を解決するための手段】本発明者らは、リボース
の選択輸送剤について鋭意研究を重ねた結果、水酸化バ
リウム又は水酸化ストロンチウムと特定のリン酸ジエス
テルとの反応により得られる脂溶性バリウム又はストロ
ンチウム錯体は安価であり、特にリボースを、カルシウ
ム錯体に比較してより迅速に輸送する能力に優れている
ことを見出し、この知見に基づいて本発明を完成するに
至った。Means for Solving the Problems The present inventors have made intensive studies on a selective transport agent for ribose, and as a result, have found that fat-soluble barium hydroxide obtained by the reaction of barium hydroxide or strontium hydroxide with a specific phosphoric diester. Alternatively, a strontium complex was found to be inexpensive, and in particular, was superior in the ability to transport ribose more quickly than a calcium complex, and based on this finding, the present invention was completed.
【０００６】すなわち、本発明は、一般式 Ｍ（ＯＰＯ（ＯＲ）2）2 （Ｉ） 〔式中のＭはバリウム又はストロンチウム、Ｒは２−エ
チルヘキシル基である〕で表わされる脂溶性バリウム又
はストロンチウム錯体から成るリボースの選択輸送剤を
提供するものである。That is, the present invention relates to a fat-soluble barium or strontium represented by the general formula: M (OPO (OR) 2 ) 2 (I) wherein M is barium or strontium, and R is a 2-ethylhexyl group. An object of the present invention is to provide a selective ribose transport agent comprising a complex.
【０００７】[0007]
【発明の実施の形態】本発明の前記一般式（Ｉ）で表わ
される脂溶性バリウム又はストロンチウム錯体から成る
リボースの選択輸送剤は、水酸化バリウム又は水酸化ス
トロンチウムと、一般式 ＨＯＰＯ（ＯＲ）2 （II） （式中のＲは前記と同じ意味を持つ）で表わされるリン
酸ジエステルとを反応させることにより製造することが
できる。BEST MODE FOR CARRYING OUT THE INVENTION The selective transport agent for ribose comprising a fat-soluble barium or strontium complex represented by the above general formula (I) of the present invention is composed of barium hydroxide or strontium hydroxide, and a general formula HOPO (OR) 2 (II) (wherein R has the same meaning as described above).
【０００８】上記の反応は、溶媒中で行なうのが好まし
く、この溶媒としては、例えばベンゼン、トルエン、キ
シレンなどの芳香族炭化水素、ｎ−ヘキサン、シクロヘ
キサン、ｎ−ヘプタンなどの脂肪族若しくは脂環式炭化
水素、クロロホルム、エチレンクロリドなどのハロゲン
化炭化水素、ジオキサン、テトラヒドロフランなどのエ
ーテル類などを挙げることができるが、特にクロロホル
ムが好適である。The above-mentioned reaction is preferably carried out in a solvent such as aromatic hydrocarbons such as benzene, toluene and xylene, and aliphatic or alicyclic rings such as n-hexane, cyclohexane and n-heptane. Examples thereof include halogenated hydrocarbons such as formula hydrocarbons, chloroform and ethylene chloride, and ethers such as dioxane and tetrahydrofuran, and chloroform is particularly preferred.
【０００９】この上記の反応におけるリン酸ジエステル
と水酸化バリウム又は水酸化ストロンチウムとの使用割
合については、水酸化バリウム又は水酸化ストロンチウ
ム１モルに対し、リン酸ジエステルを２モル以上、好ま
しくは２〜４モル、より好ましくは２〜２．５モルの割
合で用いるのが望ましい。反応温度は、使用する原料の
種類により変化するが、一般には、０〜１００℃好まし
くは１０〜５０℃の範囲で選ばれる。In the above reaction, the proportion of the phosphoric diester to the barium hydroxide or strontium hydroxide is at least 2 mol, preferably 2 to 2 mol per mol of barium hydroxide or strontium hydroxide. It is desirable to use 4 moles, more preferably 2 to 2.5 moles. The reaction temperature varies depending on the type of raw materials used, but is generally selected in the range of 0 to 100 ° C, preferably 10 to 50 ° C.
【００１０】このようにして、一般式（Ｉ）で表わされ
る脂溶性バリウム又はストロンチウム錯体が生成する
が、このものは、反応終了液から公知の手段により単離
し、精製してもよい。また、反応混合物をそのまま、又
は所望により濃度調整を行ったのち、リボースの選択輸
送に供してもよい。In this way, a fat-soluble barium or strontium complex represented by the general formula (I) is produced, which may be isolated and purified from the reaction solution by a known means. Alternatively, the reaction mixture may be subjected to selective transport of ribose as it is or after adjusting the concentration as desired.
【００１１】前記一般式（Ｉ）で表わされる脂溶性バリ
ウム又はストロンチウム錯体は、溶液Ａ−溶液Ｍ−溶液
Ｂから成る液膜系において、一方の容液Ａ中のリボース
を選択的に溶液Ｂに輸送する機能を有している。The fat-soluble barium or strontium complex represented by the general formula (I) is used for selectively converting ribose in one of the solutions A to the solution B in a liquid film system consisting of a solution A, a solution M and a solution B. Has the function of transport.
【００１２】本発明の前記一般式（Ｉ）で表わされる脂
溶性バリウム又はストロンチウム錯体を用いてリボース
の輸送を行うには、２種類の溶液Ａ及びＢを、当該脂溶
性バリウム又はストロンチウム錯体を介して間接的に接
触させればよい。例えば、（１）脂溶性バリウム錯体を
溶液Ａと溶液Ｂに対して実質上非混和性の有機溶媒に溶
解させ、この脂溶性バリウム錯体の溶液を中間溶液とし
て、溶液Ａ及び溶液Ｂを間接的に接触させる方法、
（２）隔膜により仕切りられた区画内に収容された脂溶
性バリウム錯体の溶液を介して、溶液Ａ及び溶液Ｂを間
接的に接触させる方法、（３）高分子膜やろ紙などの支
持体に支持させた脂溶性バリウム錯体を介して、溶液Ａ
及び溶液Ｂを間接的に接触させる方法などを用いること
ができる。In order to carry out ribose transport using the fat-soluble barium or strontium complex represented by the general formula (I) of the present invention, two types of solutions A and B are transferred via the fat-soluble barium or strontium complex. The contact may be made indirectly. For example, (1) a fat-soluble barium complex is dissolved in an organic solvent that is substantially immiscible with the solution A and the solution B, and the solution A and the solution B are indirectly treated using the solution of the fat-soluble barium complex as an intermediate solution. How to contact the
(2) a method in which solution A and solution B are indirectly contacted via a solution of a fat-soluble barium complex housed in a section partitioned by a diaphragm; (3) a support such as a polymer membrane or a filter paper. Solution A via the supported fat-soluble barium complex
And a method of indirectly bringing the solution B into contact.
【００１３】次に、添付図面に従い、溶液Ａと溶液Ｂと
を、脂溶性バリウム又はストロンチウム錯体の溶液Ｍを
介して接触させることにより、リボースの輸送を行う場
合の具体例を示す。図１は、本発明の脂溶性バリウム又
はストロンチウム錯体から成る選択輸送剤を用い、リボ
ースの輸送を行う場合の装置の１例の説明図であって、
Ｕ字型の装置１は、筒状容器２及び３とそれらの下部を
連結する連結管４と撹拌機５及び６から構成されてい
る。Next, a specific example in which ribose is transported by bringing solution A and solution B into contact with each other via a solution M of a fat-soluble barium or strontium complex will be described with reference to the accompanying drawings. FIG. 1 is an explanatory view of one example of an apparatus in the case of transporting ribose using a selective transport agent comprising a fat-soluble barium or strontium complex of the present invention,
The U-shaped device 1 is composed of cylindrical containers 2 and 3, a connecting pipe 4 connecting lower portions thereof, and agitators 5 and 6.
【００１４】この装置１に対し、まず、脂溶性バリウム
又はストロンチウム錯体の溶液Ｍを中間液層として入
れ、次いで、一方の筒状容器２に溶液Ａを、他方の筒状
容器３に溶液Ｂを入れる。なお、溶液Ｍは溶液Ａ及びＢ
と事実上非混和性のものである。First, a solution M of a fat-soluble barium or strontium complex is put into the apparatus 1 as an intermediate liquid layer, and then a solution A is placed in one cylindrical vessel 2 and a solution B is placed in the other cylindrical vessel 3. Put in. In addition, the solution M is the solution A and the solution B.
And are virtually immiscible.
【００１５】前記溶液Ａは移送対象となるリボースを含
むものであり、通常水溶液が用いられるが、アルコール
などの有機溶媒溶液も適用される。一方、溶液Ｂは、移
送されるリボースを受け取るためのもので、通常水が用
いられる。溶液Ｍの調製に用いられる溶媒としては、溶
液Ａ及び溶液Ｂと実質状非混和性のもの、例えば溶液Ａ
及び溶液Ｂが水溶液である場合には、クロロホルム、四
塩化炭素、ジクロロエタンなどのハロゲン化炭化水素、
ベンゼン、トルエンなどの炭化水素、へキシルアルコー
ル、オクチルアルコールなどの水難溶性アルコールなど
が挙げられる。The solution A contains ribose to be transferred. Usually, an aqueous solution is used, but an organic solvent solution such as alcohol is also applicable. On the other hand, the solution B is for receiving the transferred ribose, and usually uses water. Solvents used for preparing solution M include those which are substantially immiscible with solution A and solution B, for example, solution A
And when the solution B is an aqueous solution, chloroform, carbon tetrachloride, halogenated hydrocarbons such as dichloroethane,
Examples include hydrocarbons such as benzene and toluene, and poorly water-soluble alcohols such as hexyl alcohol and octyl alcohol.
【００１６】このようにして、溶液Ａ及び溶液Ｂを間接
的に接触させることにより、溶液Ａ中のリボースが脂溶
性バリウム又はストロンチウム錯体に捕捉され、このリ
ボースを捕捉した脂溶性バリウム又はストロンチウム錯
体は、溶液Ｂと接触し、その中の捕捉したリボースを放
出する。このようにして、溶液Ａ中のリボースが溶液Ｂ
中に効果的に輸送される。In this way, by bringing the solution A and the solution B into indirect contact, the ribose in the solution A is captured by the fat-soluble barium or strontium complex, and the fat-soluble barium or strontium complex capturing the ribose becomes , Contacting with solution B to release the entrapped ribose therein. In this way, the ribose in the solution A
Effectively transported inside.
【００１７】本発明の脂溶性バリウム又はストロンチウ
ム錯体から成るリボースの選択輸送剤は、Ｄ−リボース
を最も効率よく輸送し、またＤ−フルクトース、Ｄ−フ
コース、Ｌ−ラムノース、Ｄ−マンノース、Ｄ−アラビ
ノース、Ｄ−キシロースもある程度輸送するのに対し、
Ｄ−グルコース及びＤ−ガラクトースはほとんど輸送し
ない。これは、糖類の各水酸基の相対配置と疎水性基の
存在の有無が、輸送の選択性に大きく影響しているもの
と考えられる。The selective transfer agent for ribose comprising the fat-soluble barium or strontium complex of the present invention transports D-ribose most efficiently, and furthermore, D-fructose, D-fucose, L-rhamnose, D-mannose, D-mannose, Arabinose and D-xylose also transport to some extent,
D-glucose and D-galactose hardly transport. It is considered that the relative arrangement of each hydroxyl group of the saccharide and the presence / absence of a hydrophobic group greatly influence the transport selectivity.
【００１８】[0018]
【発明の効果】本発明の脂溶性バリウム又はストロンチ
ウム錯体から成るリボースの選択輸送剤は、種々の単糖
類が存在する水溶液から、リボースを効率よく液膜を通
して輸送する能力を有し、選択的かつ連続的に抽出する
ことができる。Industrial Applicability The selective ribose transport agent comprising a fat-soluble barium or strontium complex according to the present invention has the ability to transport ribose efficiently from an aqueous solution containing various monosaccharides through a liquid membrane, and is capable of selectively transporting ribose. Can be extracted continuously.
【００１９】また、この脂溶性バリウム又はストロンチ
ウム錯体は、それぞれ水酸化バリウム、水酸化ストロン
チウムとリン酸ジエステルとから容易に得られるので、
安価である。The fat-soluble barium or strontium complex can be easily obtained from barium hydroxide, strontium hydroxide and phosphoric diester, respectively.
It is cheap.
【００２０】[0020]
【実施例】次に、実施例により本発明をさらに詳細に説
明するが、本発明は、これらの例によってなんら限定さ
れるものではない。Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
【００２１】実施例１ （１）脂溶性バリウム錯体溶液の調製 クロロホルム３００ｍｌ中に、水酸化バリウム１０ミリ
モル及びリン酸ジ−２−エチルヘキシル２０ミリモルを
加え、室温で１２時間かきまぜ、反応させて、脂溶性バ
リウム錯体（Ｂａ［ＯＰＯ（ＯＣ8Ｈ17）2〕2）を含む
溶液を調製した。 （２）単糖類の輸送実験 溶液Ａとして、０．５Ｍ Ｄ−グルコース、０．５Ｍ
Ｄ−ガラクトース、０．５Ｍ Ｄ−マンノース、０．５
Ｍ Ｄ−リボース、０．５Ｍ Ｄ−アラビノース、０．
５Ｍ Ｄ−キシロース、０．５Ｍ Ｄ−フコース、０．
５Ｍ Ｌ−ラムノース及び０．５Ｍ Ｄ−フルクトース
を含有する水溶液１５ｍｌを調製した。Example 1 (1) Preparation of fat-soluble barium complex solution In 300 ml of chloroform were added 10 mmol of barium hydroxide and 20 mmol of di-2-ethylhexyl phosphate, and the mixture was stirred at room temperature for 12 hours to react. A solution containing a soluble barium complex (Ba [OPO (OC 8 H 17 ) 2 ] 2 ) was prepared. (2) Monosaccharide transport experiment As solution A, 0.5 M D-glucose, 0.5 M
D-galactose, 0.5M D-mannose, 0.5
MD-ribose, 0.5MD-arabinose, 0.
5M D-xylose, 0.5M D-fucose, 0.
15 ml of an aqueous solution containing 5 M L-rhamnose and 0.5 M D-fructose was prepared.
【００２２】次に、図１に示す装置に、ます中間液層
（溶液Ｍ）として上記（１）で得られたバリウム錯体溶
液をクロロホルムとして３０ｍｌ（バリウム錯体１ミリ
モル含有）入れ、次いで一方の筒状容器２に上記溶液Ａ
１５ｍｌを、他方の筒状容器３に溶液Ｂとして水１５
ｍｌを入れ、輸送実験を２５℃にて行った（撹絆機回転
数：２００ｒｐｍ）。２日間日経過後、溶液Ａから溶液
Ｂへ輸送された単糖類の量を求めた。その結果を表１に
示す。Next, 30 ml (containing 1 mmol of barium complex) of the barium complex solution obtained in the above (1) as an intermediate liquid layer (solution M) was added to the apparatus shown in FIG. Solution A in a container 2
15 ml of water 15 as solution B in the other cylindrical container 3.
ml, and a transport experiment was performed at 25 ° C. (rotation speed of a stirring machine: 200 rpm). After 2 days, the amount of monosaccharides transported from solution A to solution B was determined. Table 1 shows the results.
【００２３】[0023]
【表１】 [Table 1]
【００２４】表１から明らかなように、Ｄ−リボースが
最も効率よく輸送され、Ｄ−フルクトース、Ｄ−フコー
ス、Ｌ−ラムノース、Ｄ−マンノース、Ｄ−アラビノー
ス、Ｄ−キシロースもある程度輸送可能なのに対して、
Ｄ−グルコース及びＤ−ガラクトースはほとんど輸送さ
れなかった。As is clear from Table 1, D-ribose is transported most efficiently, while D-fructose, D-fucose, L-rhamnose, D-mannose, D-arabinose, and D-xylose can be transported to some extent. hand,
D-glucose and D-galactose were hardly transported.
【００２５】実施例２ （１）脂溶性バリウム錯体 クロロホルム３０ｍｌ中に、水酸化バリウム１ミリモル
及びリン酸ジ−２−エチルヘキシル４ミリモルを加え、
室温で１２時間かきまぜ、反応させて、脂溶性バリウム
錯体（Ｂａ［ＯＰＯ（ＯＣ8Ｈ17）2］2）を含む溶液を
調製した。Example 2 (1) Fat-soluble barium complex In 30 ml of chloroform, 1 mmol of barium hydroxide and 4 mmol of di-2-ethylhexyl phosphate were added.
The mixture was stirred at room temperature for 12 hours and reacted to prepare a solution containing a fat-soluble barium complex (Ba [OPO (OC 8 H 17 ) 2 ] 2 ).
【００２６】（２）Ｄ−リボースの輸送実験 溶液Ａとして０．５Ｍ Ｄ−リボース含有溶液１５ｍｌ
を、溶液Ｍとして上記（１）で得られたバリウム錯体溶
液（クロロホルムとして３０ｍｌ）を、溶液Ｂとして水
を用い、実施例１−（２）と同様にして輸送実験を行
い、２日間経過後のＤ−リボースの輸送量を求めた。そ
の結果、Ｄ−リボースの輸送量は３．０ミリモルであっ
た。(2) D-Ribose Transport Experiment 15 ml of a 0.5 M D-ribose-containing solution as solution A
Was transported in the same manner as in Example 1- (2) using the barium complex solution (30 ml as chloroform) obtained in the above (1) as solution M and water as solution B, and after 2 days, Of D-ribose was determined. As a result, the transport amount of D-ribose was 3.0 mmol.
【００２７】実施例３ （１）脂溶性ストロンチウム錯体溶液の調製 クロロホルム３０ｍｌ中に、水酸化ストロンチウム１ミ
リモル及びリン酸ジ−２−エチルヘキシル２ミリモルを
加え、室温で１２時間かきまぜ、反応させて、脂溶性ス
トロンチウム錯体を含む溶液を調製した。Example 3 (1) Preparation of fat-soluble strontium complex solution 1 mmol of strontium hydroxide and 2 mmol of di-2-ethylhexyl phosphate were added to 30 ml of chloroform, and the mixture was stirred at room temperature for 12 hours to react. A solution containing a soluble strontium complex was prepared.
【００２８】（２）Ｄ−リボースの輸送実験 溶液Ａとして０．５Ｍ Ｄ−リボース含有水溶液１５ｍ
ｌを、溶液Ｍとして上記（１）で得られたストロンチウ
ム錯体溶液（クロロホルムとして３０ｍｌ）を、溶液Ｂ
として水を用い、実施例１−（２）と同様にして輸送実
験を行い、２日間経過後のＤ−リボースの輸送量を求め
た。その結果、Ｄ−リボースの輸送量は２．５ミリモル
であった。(2) D-Ribose Transport Experiment 15 M of a 0.5 M D-ribose-containing aqueous solution was used as solution A.
1 as a solution M, the strontium complex solution (30 ml as chloroform) obtained in the above (1), and a solution B
Using water as the sample, a transport experiment was performed in the same manner as in Example 1- (2), and the transport amount of D-ribose after two days had elapsed was determined. As a result, the transport amount of D-ribose was 2.5 mmol.
【００２９】比較例１ （１）脂溶性カルシウム錯体 クロロホルム３０ｍｌ中に、水酸化カルシウム１ミリモ
ル及びリン酸ジ−２−エチルヘキシル２ミリモルを加
え、室温で１２時間かきまぜ、反応させて、脂溶性カル
シウム錯体（Ｃａ［ＯＰＯ（０Ｃ8Ｈ17）2]2）を含む溶
液を調製した。Comparative Example 1 (1) Fat-soluble calcium complex In 30 ml of chloroform, 1 mmol of calcium hydroxide and 2 mmol of di-2-ethylhexyl phosphate were added, and the mixture was stirred at room temperature for 12 hours to react. A solution containing (Ca [OPO (0C 8 H 17 ) 2 ] 2 ) was prepared.
【００３０】（２）Ｄ−リボースの輸送実験 溶液Ａとして０．５Ｍ Ｄ−リボース含有溶液１５ｍｌ
を、溶液Ｍとして上記（１）で得られたカルシウム錯体
溶液（クロロホルムとして３０ｍｌ）を、溶液Ｂとして
水を用い、実施例１−（２）と同様にして輸送実験を行
い、２日間経過後のＤ−リボースの輸送量を求めた。そ
の結果、Ｄ−リボースの輸送量は１．２ミリモルであっ
た。(2) D-Ribose Transport Experiment 15 ml of a 0.5 M D-ribose-containing solution as solution A
Was transported in the same manner as in Example 1- (2) using the calcium complex solution (30 ml as chloroform) obtained in the above (1) as solution M and water as solution B, and after 2 days, Of D-ribose was determined. As a result, the transport amount of D-ribose was 1.2 mmol.
【００３１】比較例２ 溶液Ａとして０．５Ｍ Ｄ−リボース含有水溶液１５ｍ
ｌを、溶液Ｍとしてクロロホルム３０ｍｌにリン酸ジ−
２−エチルヘキシル２ミリモルを溶かした溶液を、溶液
Ｂとして水を用い、実施例１−（２）と同様にして輸送
実験を行い、２日間経過後のＤ−リボースの輸送量を求
めたところ、Ｄ−リボースは全く輸送されていなかっ
た。Comparative Example 2 As solution A, 15 m of an aqueous solution containing 0.5 M D-ribose
1 as a solution M in 30 ml of chloroform.
Using a solution in which 2 mmol of 2-ethylhexyl was dissolved, water was used as solution B, and a transport experiment was carried out in the same manner as in Example 1- (2). D-ribose was not transported at all.
【図１】本発明の脂溶性バリウム又はストロンチウム錯
体から成る選択輸送剤を用い、リボースの輸送を行う場
合の装置の１例の説明図。FIG. 1 is an explanatory view of an example of an apparatus in the case where ribose is transported using a selective transport agent comprising a fat-soluble barium or strontium complex of the present invention.
１ Ｕ字型装置 ２，３ 筒状容器 ４ 連結管 ５，６ 撹絆機 Ａ 溶液Ａ Ｂ 溶液Ｂ Ｍ 溶液Ｍ DESCRIPTION OF SYMBOLS 1 U-shaped apparatus 2, 3 Tubular container 4 Connecting pipe 5, 6 Stirrer A Solution A B Solution B M Solution M
───────────────────────────────────────────────────── フロントページの続き (72)発明者 平谷 和久 茨城県つくば市東１丁目１番 工業技術 院物質工学工業技術研究所内 (56)参考文献 特開 平８−209106（ＪＰ，Ａ) ──────────────────────────────────────────────────続 き Continuing from the front page (72) Inventor Kazuhisa Hiratani 1-1-1 Higashi, Tsukuba City, Ibaraki Pref.
Claims (1)
チルヘキシル基である〕で表わされる脂溶性バリウム又
はストロンチウム錯体からなるリボースの選択輸送剤。1. Selective transport of ribose comprising a fat-soluble barium or strontium complex represented by the general formula M (OPO (OR) 2 ) 2 wherein M is barium or strontium, and R is a 2-ethylhexyl group. Agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22691495A JP2716082B2 (en) | 1995-09-05 | 1995-09-05 | Ribose selective transporter |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22691495A JP2716082B2 (en) | 1995-09-05 | 1995-09-05 | Ribose selective transporter |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0967384A JPH0967384A (en) | 1997-03-11 |
| JP2716082B2 true JP2716082B2 (en) | 1998-02-18 |
Family
ID=16852585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22691495A Expired - Lifetime JP2716082B2 (en) | 1995-09-05 | 1995-09-05 | Ribose selective transporter |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2716082B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004046356A1 (en) * | 2004-09-24 | 2006-03-30 | Clariant Gmbh | Process for the preparation of alk (en) ylphosphoric acid ester salts |
| HUP0700490A2 (en) * | 2007-07-24 | 2009-08-28 | H4Sep Kutatasi Es Tanacsado Kf | Extraction method and apparatus thereof |
-
1995
- 1995-09-05 JP JP22691495A patent/JP2716082B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0967384A (en) | 1997-03-11 |
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