JPWO2017195884A1 - 多孔質セルロース媒体の製造方法 - Google Patents
多孔質セルロース媒体の製造方法 Download PDFInfo
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- JPWO2017195884A1 JPWO2017195884A1 JP2018517092A JP2018517092A JPWO2017195884A1 JP WO2017195884 A1 JPWO2017195884 A1 JP WO2017195884A1 JP 2018517092 A JP2018517092 A JP 2018517092A JP 2018517092 A JP2018517092 A JP 2018517092A JP WO2017195884 A1 JPWO2017195884 A1 JP WO2017195884A1
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- cellulose
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- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000004964 aerogel Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229940125644 antibody drug Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229960000074 biopharmaceutical Drugs 0.000 description 1
- PFYXSUNOLOJMDX-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O PFYXSUNOLOJMDX-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
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- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
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- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
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- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
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- 150000008163 sugars Chemical class 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000002463 transducing effect Effects 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
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Abstract
Description
前記セルロースアセテート溶液と、脱アセチル化剤と、触媒とを混合して混合溶液を得る工程、
を備える、多孔質セルロース媒体の製造方法。
項2. 前記触媒が、アルコキシド、アミン化合物、弱塩基性無機化合物、及びN−ヒドロキシアミン誘導体からなる群より選択される少なくとも1種である、項1に記載の多孔質セルロース媒体の製造方法。
項3. 前記アミン化合物が第3級アミンであり、前記弱塩基性無機化合物が炭酸塩である、項2に記載の多孔質セルロース媒体の製造方法。
項4. 前記混合溶液を成形容器内で静置した状態で、前記セルロースアセテートの脱アセチル化反応を進行させて、多孔質セルロース媒体により構成された多孔質セルロースモノリスを得る、項1〜3のいずれかに記載の多孔質セルロース媒体の製造方法。
項5. 前記混合溶液と、前記混合溶液とは混和しない分散媒体とを混合し、前記混合溶液が分散した状態で、前記セルロースアセテートの脱アセチル化反応を進行させて、多孔質セルロース媒体により構成された多孔質セルロース粒子を得る、項1〜4のいずれかに記載の多孔質セルロース媒体の製造方法。
項6. 前記分散媒体が流動パラフィンである、項5に記載の多孔質セルロース媒体の製造方法。
項7. 項1〜6のいずれかに記載の製造方法により得られた多孔質セルロース媒体に、アフィニティーリガンドを固定化する工程を備える、吸着体の製造方法。
項8. 前記アフィニティーリガンドが、プロテインA、プロテインG、プロテインL、及びこれらの機能性変異体からなる群より選ばれる少なくとも1種である、項7に記載の吸着体の製造方法。
項9. 項1〜6のいずれかに記載の製造方法により得られた多孔質セルロース媒体にアフィニティーリガンドを結合させて得られた吸着体と、標的物質を含む混合物とを接触させて、前記アフィニティーリガンドに前記標的物質を結合させる第一の工程、及び
前記吸着体の前記アフィニティーリガンドに結合した前記標的物質を分離する第二の工程
を含む、標的物質の精製方法。
セルロースジアセテート(酢化度55% 置換度2.5)0.40gをDMSO4.65gに溶解した。ここに1.00mLのメタノールを加えると、いったん沈殿が生成したが、よくかき混ぜると再び均一な溶液(セルロースジアセテート溶液)となり、これを氷冷静置した。一方、DMSOとメタノールをそれぞれ0.50mLずつ混和し、これに20%ナトリウムエトキシド/エタノール溶液(和光純薬社製)1.04mgを混ぜ、氷冷した。次に、この溶液と、セルロースジアセテート溶液とを手早く混ぜ、1cm角の柱状セルに流し込み、引き続き氷冷した。柱状セル内の液は、約2時間で固化した。更に2時間氷冷後、一夜室温に置いた後、柱状セルから四角柱状の多孔質セルロースモノリスを取り出し、繰り返し水洗した。得られた多孔質セルロースモノリスは、7.0mm角の柱状であった。
セルロースジアセテート(酢酸含量55%)のDMSO溶液(セルロースジアセテート:7.88質量%)51.6gにメタノール10mLを加え、よく攪拌して均一な透明溶液とし、これを氷冷した(溶液1)。一方、流動パラフィン約1000mLにDMSO/メタノール46.5:15(v/v)の混合溶液(約50ml)を1日接触させた後、後者を分液除去することにより、DMSO/メタノールを飽和させた流動パラフィン(関東化学(株)製、比重0.89−0.91)800mlを得た。これを1L容器中にいれて、氷冷した(溶液2)。また、DMSO5.0mL、メタノール5.0mL、20%ナトリウムエトキシド/エタノール溶液(和光純薬社製)187mgを混合し、氷冷した(溶液3)。次に、溶液1と溶液3を混合して、良く攪拌した後、溶液2に投入し、直径2cmの攪拌羽を用い、740rpm、5分間の条件で攪拌した。攪拌後、4時間静置氷冷した後、室温で一夜放置した。次に、水を約200mL加え、穏やかに攪拌した後、下層(水相)を別の容器に吸い上げた。水を加えて下層を吸い上げる操作を合計3回繰り返して、セルロース成分を抽出した。次に、得られた水相を静置し、上澄みを傾瀉して、200mLほどにまで濃縮した後、1gのNaOHを加えて更に一夜静置し、多孔質セルロース粒子を得た。得られたゲル粒子の光学顕微鏡写真を図2に示す。光学顕微鏡写真から、多孔質セルロース粒子の直径は、約50μm以下程度の球状粒子が主であることが確認された。
セルロースジアセテート16.03gをDMSO129.42gに溶かし、溶液を調製した。本溶液3.04gにメタノール7.6mLをゆっくり混和し、透明な溶液を得、氷冷した。一方でリチウムメトキシドの10%メタノール溶液(和光純薬(株)製)0.117gをメタノール1.94g、DMSO2.77gに希釈した液を調製し、氷冷した。このリチウムメトキシドの希釈液の1.00mLを前記のセルローシジアセテート溶液に混和し、手早く混ぜた後、二つの1cm角柱型のセルに分注した。セルの一方は氷冷したところ、約3時間後に流動性を失い、一方は約20度の水に浸漬したところ、30分後に流動性を失い、いずれも白色半透明のゲル状固体を与えた。
セルロースジアセテート(酢酸含量55%)7.22gをホルムアミド112.21gに分散し、攪拌しながら約30分125℃に加熱すると、透明な溶液になり、これを室温に冷却した。翌日、やわらかいゲル状となったこの溶液の8.68gを採取し、メタノール1.58gを混和すると、最終的に流動性の溶液となった。一方で、炭酸カリウム120mgをホルムアミド2mLに溶解し、両液を氷冷した。炭酸カリウム溶液の溶液1.00mLを、前記のメタノールを添加した溶液に加え、よく攪拌しながら、3分間0℃に保ったのち、1辺が1.00cmの四角柱状のプラスチックセル2本に注いだ。1本は0℃に保つと、2時間後に流動性を失った。もう1本は室温、23℃に静置すると、23分で流動性を失った。一昼夜放置した後、少し収縮して容器から離れたゲル状固体を、純水中で、水を入れ替えながら2日間、良く洗浄した。得られたゲルは、いずれも不透明白色固体であった。ゲルの一部を切り取り、表面に付着した水をろ紙で吸い取った後に秤量し、更に80℃、常圧で3時間、ついで80℃、減圧(約1Torr)で3時間乾燥し、収縮して小さく透明になったものを秤量し、元のゲルの含水率を調べた。0℃でゲル化したものは163.2mgであり、乾燥後に11.8gとなったため、含水率は92.8%であった。また、23℃でゲル化したもの133.5mgが乾燥後に9.5mgとなったため、含水率は92.9%であった。
実施例2と同様に事前にホルムアミドとメタノールの1:4v/v混合液と接触させ、これらを飽和させた流動パラフィン790mLに、日本エマルジョン社製TSG−10 384mgを加えて60℃に加温して後者を溶解させた後、20℃に保温した(溶液5)。一方、実施例4で用いたセルロースジアセテートのホルムアミド溶液109.2gに、メタノール19.3gを混和し、流動性の溶液とし、20℃に保温した(溶液4)。溶液4に、炭酸カリウム620mgをホルムアミド12.9gに溶解した液(溶液6)を投入、混和した。混和後、速やかに混合液を溶液5中に投入、攪拌翼を用いて約400rpmで8分間攪拌した。一昼夜静置した後、水150mLを加え、容器を回転して生成した白色粉末状のビーズを水に抽出、分液した。同じ操作を更にもう2回繰り返し、水抽出液を併せた。水中での沈降、上澄みの傾寫を繰り返し、沈降体積70mLのビーズを得た。この光学顕微鏡写真を図3に示す。また、得られた粒子をメタノールと2−プロパノールで逐次洗浄後、乾燥、KBrディスク法で測定した赤外吸収スペクトルを図4に示す。赤外吸収スペクトルにおいて、1735cm-1付近にアセチル基のカルボニル基と思われる吸収を示すが、2920cm-1付近の本来弱い吸収より更に弱く、実質的にセルロースであると見做せる。
Claims (9)
- セルロースアセテートが溶媒に溶解したセルロースアセテート溶液を準備する工程、及び
前記セルロースアセテート溶液と、脱アセチル化剤と、触媒とを混合して混合溶液を得る工程、
を備える、多孔質セルロース媒体の製造方法。 - 前記触媒が、アルコキシド、アミン化合物、弱塩基性無機化合物、及びN−ヒドロキシアミン誘導体からなる群より選択される少なくとも1種である、請求項1に記載の多孔質セルロース媒体の製造方法。
- 前記アミン化合物が第3級アミンであり、前記弱塩基性無機化合物が炭酸塩である、請求項2に記載の多孔質セルロース媒体の製造方法。
- 前記混合溶液を成形容器内で静置した状態で、前記セルロースアセテートの脱アセチル化反応を進行させて、多孔質セルロース媒体により構成された多孔質セルロースモノリスを得る、請求項1〜3のいずれかに記載の多孔質セルロース媒体の製造方法。
- 前記混合溶液と、前記混合溶液とは混和しない分散媒体とを混合し、前記混合溶液が分散した状態で、前記セルロースアセテートの脱アセチル化反応を進行させて、多孔質セルロース媒体により構成された多孔質セルロース粒子を得る、請求項1〜4のいずれかに記載の多孔質セルロース媒体の製造方法。
- 前記分散媒体が流動パラフィンである、請求項5に記載の多孔質セルロース媒体の製造方法。
- 請求項1〜6のいずれかに記載の製造方法により得られた多孔質セルロース媒体に、アフィニティーリガンドを固定化する工程を備える、吸着体の製造方法。
- 前記アフィニティーリガンドが、プロテインA、プロテインG、プロテインL、及びこれらの機能性変異体からなる群より選ばれる少なくとも1種である、請求項7に記載の吸着体の製造方法。
- 請求項1〜6のいずれかに記載の製造方法により得られた多孔質セルロース媒体にアフィニティーリガンドを結合させて得られた吸着体と、標的物質を含む混合物とを接触させて、前記アフィニティーリガンドに前記標的物質を結合させる第一の工程、及び
前記吸着体の前記アフィニティーリガンドに結合した前記標的物質を分離する第二の工程、
を含む、標的物質の精製方法。
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