JPWO2008029785A1 - 多糖誘導体及びそれを含有する光学異性体用分離剤 - Google Patents
多糖誘導体及びそれを含有する光学異性体用分離剤 Download PDFInfo
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- JPWO2008029785A1 JPWO2008029785A1 JP2008533156A JP2008533156A JPWO2008029785A1 JP WO2008029785 A1 JPWO2008029785 A1 JP WO2008029785A1 JP 2008533156 A JP2008533156 A JP 2008533156A JP 2008533156 A JP2008533156 A JP 2008533156A JP WO2008029785 A1 JPWO2008029785 A1 JP WO2008029785A1
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- substituent
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- amino group
- hydroxyl group
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- 150000004676 glycans Chemical class 0.000 title claims abstract 21
- 125000001424 substituent group Chemical group 0.000 claims abstract description 288
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 148
- 125000003277 amino group Chemical group 0.000 claims abstract description 141
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 31
- 125000006239 protecting group Chemical group 0.000 claims description 56
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- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 8
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- 239000013067 intermediate product Substances 0.000 description 83
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- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000010830 demodification reaction Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 150000002243 furanoses Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- AIHDCSAXVMAMJH-GFBKWZILSA-N levan Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@@H]1[C@@H](O)[C@H](O)[C@](CO)(CO[C@@H]2[C@H]([C@H](O)[C@@](O)(CO)O2)O)O1 AIHDCSAXVMAMJH-GFBKWZILSA-N 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 239000011654 magnesium acetate Substances 0.000 description 1
- 235000011285 magnesium acetate Nutrition 0.000 description 1
- 229940069446 magnesium acetate Drugs 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical class NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229920005640 poly alpha-1,3-glucan Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003214 pyranose derivatives Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 238000002444 silanisation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000007613 slurry method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000002463 transducing effect Effects 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
−CO−R (I)
−CO−NH−R (II)
−R (III)
−CO−R (I)
−CO−NH−R (II)
−R (III)
−CO−R (I)
−CO−NH−R (II)
−R (III)
すなわち、多糖の構成単位が有する2位の水酸基又はアミノ基を前記一般式(I)〜(III)で表される第一の置換基で修飾する工程と、次いで前記構成単位が有する3位の水酸基又はアミノ基を前記一般式(I)〜(III)で表される、前記第一の置換基とは異なる第二の置換基で修飾する工程とを含む方法によって本発明の多糖誘導体を製造することができる。前記第一の置換基は前記一般式(I)で表される置換基であることが好ましく、前記第二の置換基は、2位の修飾に用いられた置換基とは異なる構造の置換基であれば、前記一般式(I)で表される置換基であってもよい。
(1) 4−methoxytrityl chlorideによる6位の保護
DS3-=0.95(NMR)
DS6-=0.95(NMR)
DS3-=0.95(NMR)
DS6-=0.93(NMR)
DS(3,5-dimethyl)3-=0.51(NMR)
DS(3,5-dimethyl)6-=0.49(NMR)
DS2-=1.04/0.90(NMR/元素分析)
DS3,6-=1.96/2.10(NMR/元素分析)
元素分析: 分析値 C 66.32% H 5.80% N 5.12%
(計算値 C 66.42% H 5.75% N 5.00%)
DS2-=1.00/1.23(NMR/元素分析)
DS3,6-=2.00/1.77(NMR/元素分析)
元素分析: 分析値 C 50.49% H 3.20% N 4.14%
(計算値 C 50.49% H 3.14% N 4.36%)
得られたアミロース誘導体である目的化合物1〜5をそれぞれ表面処理したシリカゲルに担持し、Hexane/IPA=9/1の溶離液を用い、粒径分別を行った後、4.6mm(i.d.)×250mm又は2.0mm(i.d.)×250mmのカラムへ、スラリー法にて充填し、カラムを作製した。以下作製したカラムをそれぞれカラム1、2、3、4、5とする。
今回合成した、光学異性体用分離剤として新規なアミロース誘導体である目的化合物1〜5の光学分割能を、溶離液にHexane/IPA=9/1の混合溶剤を用い、下記構造式群に示す10種のラセミ体1〜10により評価した。カラム1〜7における多糖誘導体における置換基の位置と種類を表2に示し、光学分割能の評価結果を表3に示す。
k1’=(t1−t0)/t0 (1)
k2’=(t2−t0)/t0 (2)
α=k2’/k1’ (3)
合成例9で得られたアミロース誘導体である目的化合物6について、表面処理したシリカゲルに目的化合物6をコーティングし、得られたシリカゲルをカラムに充填し、カラム8を作製した。また合成例10で得られたアミロース誘導体である目的化合物7を表面処理したシリカゲルにコーティングし、得られたシリカゲルをカラムに充填し、カラム9を作製した。これらのカラムの光学分割能を、前記構造式で示した10種のラセミ体1〜10の光学分割により評価した。この光学分割は、カラム8については前記分離条件aの条件で、カラム9については前記分離条件aの条件でそれぞれ行った。カラム8及び9における多糖誘導体における置換基の位置と種類を表6に示し、光学分割能の評価結果を表7に示す。置換基の種類と位置との違いによる光学分割能を比べる観点から、表7には、2位がベンゾエートの誘導体を充填剤に用いたカラム(カラム2及び5)及び2、3、6位の置換基が全て同じである充填剤を用いたカラム(カラム6及び7)の結果も併せて示した。
Claims (22)
- 多糖の構成単位が有する水酸基又はアミノ基のうちの少なくとも2位と3位の水酸基又はアミノ基の水素原子が、下記一般式(I)〜(III)で表される異なる置換基に置き換えられた構造を含むことを特徴とする多糖誘導体。
−CO−R (I)
−CO−NH−R (II)
−R (III)
(一般式(I)〜(III)中、Rはヘテロ原子を含んでもよい脂肪族又は芳香族炭化水素基であり、さらに置換基を有していてもよい。) - 前記構成単位における2位の水酸基又はアミノ基の水素原子が前記一般式(I)で表される置換基に置き換えられた構造を含むことを特徴とする請求項1記載の多糖誘導体。
- 前記構成単位における2位の水酸基又はアミノ基の水素原子が前記一般式(II)で表される置換基に置き換えられた構造を含むことを特徴とする請求項1記載の多糖誘導体。
- 前記構成単位における3位の水酸基又はアミノ基の水素原子が前記一般式(II)で表される置換基に置き換えられた構造を含むことを特徴とする請求項1〜3のいずれか一項に記載の多糖誘導体。
- 前記構成単位は6位に水酸基又はアミノ基をさらに有する6炭糖であり、
前記構成単位における6位の水酸基又はアミノ基の水素原子が前記一般式(I)〜(III)のいずれかで表される置換基に置き換えられた構造をさらに含むことを特徴とする請求項1〜4のいずれか一項に記載の多糖誘導体。 - 前記構成単位における3位及び6位の水酸基又はアミノ基の水素原子が前記一般式(II)で表される二つの置換基にそれぞれ置き換えられた構造を含むことを特徴とする請求項5記載の多糖誘導体。
- 前記構成単位における3位及び6位の水酸基又はアミノ基の水素原子が前記一般式(II)で表される一つの置換基に置き換えられた構造を含むことを特徴とする請求項5記載の多糖誘導体。
- 前記構成単位における3位及び6位の水酸基又はアミノ基の水素原子が前記一般式(II)で表される二以上の置換基に不規則に置き換えられた構造を含むことを特徴とする請求項5記載の多糖誘導体。
- 前記構成単位における2位及び6位の水酸基又はアミノ基の水素原子が前記一般式(II)で表される一つの置換基に置き換えられた構造を含むことを特徴とする請求項5記載の多糖誘導体。
- 前記構成単位における2位及び6位の水酸基又はアミノ基の水素原子が前記一般式(II)で表される二つの置換基に置き換えられた構造を含むことを特徴とする請求項6記載の多糖誘導体。
- 前記多糖がアミロースであることを特徴とする請求項1〜10のいずれか一項に記載の多糖誘導体。
- 多糖の構成単位が有する2位の水酸基又はアミノ基を下記一般式(I)〜(III)で表される第一の置換基で修飾する工程と、次いで前記構成単位が有する3位の水酸基又はアミノ基を下記一般式(I)〜(III)で表される、前記第一の置換基とは異なる第二の置換基で修飾する工程とを含む多糖誘導体の製造方法。
−CO−R (I)
−CO−NH−R (II)
−R (III)
(一般式(I)〜(III)中、Rはヘテロ原子を含んでもよい脂肪族又は芳香族炭化水素基であり、さらに置換基を有していてもよい。) - 前記第一の置換基が前記一般式(I)で表される置換基であることを特徴とする請求項12記載の方法。
- 前記構成単位が6位に水酸基又はアミノ基をさらに有する6炭糖であり、
2位の水酸基又はアミノ基の修飾後に、前記6位の水酸基又はアミノ基を保護基で保護する工程をさらに含むことを特徴とする請求項12又は13に記載の方法。 - 3位の水酸基又はアミノ基の修飾後に前記6位の前記保護基を外す工程と、保護基が外された6位の水酸基又はアミノ基を前記一般式(I)〜(III)で表される、前記第二の置換基とは異なる第三の置換基で修飾する工程とをさらに含むことを特徴とする請求項14記載の方法。
- 多糖の構成単位が有する2位の水酸基又はアミノ基を保護基で保護する2位保護工程と、2位が保護された前記構成単位が有する3位の水酸基又はアミノ基を下記一般式(I)〜(III)で表される第二の置換基で修飾する3位修飾工程と、3位が修飾された前記構成単位における2位の保護基を外す2位脱保護工程と、保護基が外された2位の水酸基又はアミノ基を、前記第二の置換基と同じ一般式で表されるが異なる置換基である第一の置換基で修飾する2位修飾工程とを含む多糖誘導体の製造方法。
−CO−R (I)
−CO−NH−R (II)
−R (III)
(一般式(I)〜(III)中、Rはヘテロ原子を含んでもよい脂肪族又は芳香族炭化水素基であり、さらに置換基を有していてもよい。) - 前記構成単位が6位に水酸基又はアミノ基をさらに有する6炭糖であり、
前記3位修飾工程は、前記構成単位が有する3位及び6位の両方の水酸基又はアミノ基を前記第二の置換基で修飾する工程であることを特徴とする請求項16記載の方法。 - 前記2位脱保護工程は、2位の保護基と6位の第二の置換基との両方を外す工程であり、
前記2位修飾工程は、2位及び6位の水酸基又はアミノ基の両方を前記第一の置換基で修飾する工程であることを特徴とする請求項17記載の方法。 - 前記第一及び第二の置換基が前記一般式(II)で表される置換基であることを特徴とする請求項16〜18のいずれか一項に記載の方法。
- 前記構成単位が6位に水酸基又はアミノ基をさらに有する6炭糖であり、
2位が保護された前記構成単位が有する6位の水酸基又はアミノ基を前記3位修飾工程前に保護基で保護する6位保護工程と、
前記3位修飾工程で3位が修飾された前記構成単位における6位の保護基を、前記2位脱保護工程の前に脱保護する6位脱保護工程と、
保護基が外された6位の水酸基又はアミノ基を、前記第一及び第二の置換基と同じ一般式で表されるが異なる置換基である第三の置換基で修飾する6位修飾工程とをさらに含み、
前記2位脱保護工程は、6位が修飾された前記構成単位における2位の保護基を外す工程であることを特徴とする請求項16記載の方法。 - 前記第一、第二、及び第三の置換基が前記一般式(II)で表される置換基であることを特徴とする請求項20記載の方法。
- 請求項1〜11のいずれか一項に記載の多糖誘導体を含有する光学異性体用分離剤。
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