JP6081515B2 - イオン液体を用いた生体触媒溶液および生体触媒用溶媒を使用する方法 - Google Patents
イオン液体を用いた生体触媒溶液および生体触媒用溶媒を使用する方法 Download PDFInfo
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- JP6081515B2 JP6081515B2 JP2015081210A JP2015081210A JP6081515B2 JP 6081515 B2 JP6081515 B2 JP 6081515B2 JP 2015081210 A JP2015081210 A JP 2015081210A JP 2015081210 A JP2015081210 A JP 2015081210A JP 6081515 B2 JP6081515 B2 JP 6081515B2
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/96—Stabilising an enzyme by forming an adduct or a composition; Forming enzyme conjugates
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/10—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with one amino group and at least two hydroxy groups bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/12—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/40—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton
Description
これらのヒドロキシアルキル基の中でも、2,3−ジヒドロキシプロパン−1−イル基、1,3−ジヒドロキシプロパン−2−イル基、1,3−ジヒドロキシ−2−エチルプロパン−2−イル基、1,3−ジヒドロキシ−2−ヒドロキシメチルプロパン−2−イル基、ペンタヒドロキシヘキサン−1−イル基が好ましい。
<実施例1> 化合物1
FT−IR(KBr):3392cm−1:O−H伸縮振動 2950cm−1:C−H伸縮振動 1579cm−1:COO−伸縮振動
1H−NMR (D2O 400MHz): δ 1.24 (d, 3H, CH 3 CH), δ 3.01 (t, 2H, N+CH 2 CH2OH), δ 3.71 (t, 2H, N+CH2CH 2 OH), δ 4.00 (m, 1H, CH3CH(OH)COO−).
13C−NMR (D2O 100MHz): δ 20.1 (CH3CH), δ 41.4 (N+ CH2CH2OH), δ 58.3 (N+CH2 CH2OH), δ 68.5 (CH3 CH(OH)COO−) , δ 182.5 (CH3CH(OH)COO−).
<実施例2> 化合物2
FT−IR(KBr):3392cm−1:O−H伸縮振動 2950cm−1:C−H伸縮振動 1584cm−1:COO−伸縮振動
1H−NMR (D2O 400MHz): δ 1.26 (d, 3H, CH 3 CH), δ 3.13 (t, 4H, N+CH 2 CH2OH), δ 3.79 (t, 4H, N+CH2CH 2 OH), δ 4.02 (m, 1H, CH3CH(OH)COO−).
13C−NMR (D2O 100MHz): δ 20.1 (CH3CH), δ 49.0 (N+ CH2CH2OH), δ 56.9 (N+CH2 CH2OH), δ 68.5 (CH3 CH(OH)COO−) , δ 182.5 (CH3CH(OH)COO−).
<実施例3> 化合物3
FT−IR(KBr):3360cm−1:O−H伸縮振動 2950cm−1:C−H伸縮振動 1558cm−1:COO−伸縮振動
1H−NMR (D2O 400MHz): δ 1.84 (s, 3H, CH 3 COO−), δ 3.31(t, 6H, N+CH 2 CH2OH), δ 3.85 (t, 6H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 23.3 (CH3COO−), δ 55.4 (N+ CH2CH2OH), δ 55.6 (N+CH2 CH2OH), δ 181.4 (CH3 COO−).
<実施例4> 化合物4
FT−IR(KBr):3313cm−1:O−H伸縮振動 2939cm−1:C−H伸縮振動 1591cm−1:COO−伸縮振動
1H−NMR (D2O 400MHz): δ 1.25 (d, 3H, CH 3 CH), δ 3.32 (t, 6H, N+CH 2 CH2OH), δ 3.86 (t, 6H, N+CH2CH 2 OH), δ 4.01 (m, 1H, CH3CH(OH)COO−).
13C−NMR (D2O 100MHz): δ 20.1 (CH3CH), δ 55.4 (N+ CH2CH2OH), δ 55.6 (N+CH2 CH2OH), δ 68.5 (CH3 CH(OH)COO−) , δ 182.5 (CH3CH(OH)COO−).
<実施例5> 化合物5
FT−IR(KBr):3360m−1:O−H伸縮振動 2939cm−1:C−H伸縮振動 1714cm−1:COOH伸縮振動 1563cm−1:COO−伸縮振動
1H−NMR (D2O 400MHz): δ 2.51 (s, 4H, HOOCCH 2 CH 2 COO−), δ 3.22 (t, 6H, N+CH 2 CH2OH), δ 3.84 (t, 6H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 31.4 (HOOCCH2 CH2COO−), δ 48.9 (N+ CH2CH2OH), δ 56.5 (N+CH2 CH2OH), δ 179.7 (COOH, COO−).
<実施例6> 化合物6
FT−IR(KBr):3313m−1:O−H伸縮振動 2939cm−1:C−H伸縮振動 1717cm−1:COOH伸縮振動 1588cm−1:COO−伸縮振動
1H−NMR (D2O 400MHz): δ 2.63 (m, 4H, HOOCCH 2 C(OH)(COO−)CH 2 COOH), δ 3.37 (t, 6H, N+CH 2 CH2OH), δ 3.84 (t, 6H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 43.7 (HOOCCH2C(OH)(COO−)CH2COOH), δ 55.0 (N+ CH2CH2OH), δ 55.3 (N+CH2 CH2OH), δ 73.8 (HOOCCH2 C(OH)(COO−)CH2COOH), δ 174.8 (HOOCCH2C(OH)(COO−)CH2 COOH), δ 178.7 (HOOCCH2C(OH)(COO−)CH2COOH).
<実施例7> 化合物7
FT−IR(KBr):3312m−1:O−H伸縮振動 2950cm−1:C−H伸縮振動 1593cm−1:COO−伸縮振動
1H−NMR (D2O 400MHz): δ 3.28 (t, 3H, CH 3 OCH2COO−), δ 3.39 (t, 6H, N+CH 2 CH2OH), δ 3.78 (s, 2H, CH3OCH 2 COO−), δ 3.87 (t, 6H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 55.1 (N+ CH2CH2OH), δ 55.3 (N+CH2 CH2OH), δ 58.1 (CH3OCH2COO−), δ 71.2 (CH3OCH2COO−), δ 178.0 (CH3OCH2 COO−).
<実施例8> 化合物8
FT−IR(KBr):3231cm−1:O−H伸縮振動 2972cm−1:C−H伸縮振動 1571cm−1:COO−伸縮振動
1H−NMR (D2O 400MHz): δ 1.17−1.24 (m, 3H, CH 3 CH(OH)COO−), δ 3.22−3.27 (m, 1H, CH3CH(OH)COO−), δ 3.55−3.71 (m, 1H, HOCH2CH(N+H3)CH2OH), δ 3.97−4.02 (m, 4H, HOCH 2 CH(N+H3)CH 2 OH).
13C−NMR (D2O 100MHz): δ 20.0 (CH3CH(OH)COO−), δ 53.9 (HOCH2 CH(N+H3)CH2OH), δ 59.3 (HOCH2CH(N+H3)CH2OH), δ 68.4 (CH3 CH(OH)COO−), δ 182.4 (CH3CH(OH)COO−).
<実施例9> 化合物9
FT−IR(KBr):3231cm−1:O−H伸縮振動 2937cm−1:C−H伸縮振動 1571cm−1:COO−伸縮振動
1H−NMR (D2O 400MHz): δ 0.77−0.81 (m, 3H, NH3 +C(CH2OH)2CH2CH 3 ), δ 1.17−1.24 (m, 3H, CH 3 CH(OH)COO−), δ 1.51−1.57 (m, 2H, NH3 +C(CH2OH)2CH 2 CH3), δ 3.52 (s, 4H, NH3 +C(CH 2 OH)2CH2CH3), δ 3.94−3.99 (m, 1H, CH3CH(OH)COO−).
13C−NMR (D2O 100MHz): δ 6.3 (NH3 +C(CH2OH)2CH2 CH3), δ 20.0 (CH3CH(OH)COO−), δ 23.5 (NH3 +C(CH2OH)2 CH2CH3), δ 60.3 (NH3 + C(CH2OH)2CH2CH3), δ 61.0 (NH3 +C(CH2OH)2CH2CH3), δ 68.5 (CH3 CH(OH)COO−) , δ 182.4 (CH3CH(OH)COO−).
<実施例10> 化合物10
FT−IR(KBr):3228cm−1:O−H伸縮振動 2935cm−1:C−H伸縮振動 1571cm−1:COO−伸縮振動
1H−NMR (D2O 400MHz): δ 1.15−1.17 (m, 3H, CH 3 CH(OH)COO−), δ 3.53 (s, 6H, NH3 +C(CH 2 OH)3), δ 3.91−4.11 (m, 1H, CH3CH(OH)COO−).
13C−NMR (D2O 100MHz): δ 20.0 (CH3CH(OH)COO−), δ 59.8 (NH3 + C(CH2OH)3), δ 60.7 (NH3 +C(CH2OH)3), δ 68.4 (CH3 CH(OH)COO−), δ 182.4 (CH3CH(OH)COO−).
<実施例11> 化合物11
FT−IR(KBr):3145cm−1:O−H伸縮振動 2946cm−1:C−H伸縮振動 1711cm−1:COOH伸縮振動 1572cm−1:COO−伸縮振動
1H−NMR (D2O 400MHz): δ 2.58−2.75 (m, 4H, HOOCCH 2 C(OH)(COO−)CH 2 COOH), δ 3.57 (s, 6H, NH3 +C(CH 2 OH)3).
13C−NMR (D2O 100MHz): δ 43.7 (HOOCCH2C(OH)(COO−)CH2COOH), δ 59.2 (NH3 + C(CH2OH)3), δ 61.4 (NH3 +C(CH2OH)3), δ 73.8 (HOOCCH2 C(OH)(COO−)CH2COOH), δ 174.8 (HOOCCH2C(OH)(COO−)CH2 COOH), δ 178.6 (HOOCCH2C(OH)(COO−)CH2COOH).
<実施例12> 化合物12
FT−IR(KBr):3148cm−1:O−H伸縮振動 2928cm−1:C−H伸縮振動 1574cm−1:COO−伸縮振動
1H−NMR (D2O 400MHz): δ 0.95 (t, 3H, CH 3 OCH2COO−),δ 3.48 (s, 6H, NH3 +C(CH 2 OH)3), δ 3.66 (s, 2H, CH3OCH 2 COO−).
13C−NMR (D2O 100MHz): δ 14.0 (CH3O), δ 59.2 (NH3 + C(CH2OH)3), δ 61.3 (NH3 +C(CH2OH)3),δ 69.1 (CH3OCH2COO−), δ 178.1 (CH3OCH2 COO−).
<実施例13> 化合物13
FT−IR(KBr):3388cm−1:O−H伸縮振動 2959cm−1:C−H伸縮振動
1H−NMR (D2O 400MHz): δ 2.72 (s, 3H, CH 3 SO3 −), δ 3.65 (s, 6H, NH3 +C(CH 2 OH)3).
13C−NMR (D2O 100MHz): δ 38.5 (CH3SO3 −), δ 59.4 (NH3 + C(CH2OH)3), δ 61.4 (NH3 +C(CH2OH)3).
<実施例14> 化合物14
FT−IR(KBr):3152cm−1:O−H伸縮振動 2921cm−1:C−H伸縮振動 1549cm−1:COO−伸縮振動
1H−NMR (D2O 400MHz): δ 1.76 (s, 3H, CH 3 COO−), δ 2.89−3.09 (m, 2H, HOCH2(CH(OH))3CH(OH)CH 2 NH3 +), δ 3.47−3.68 (m, 5H, HOCH 2 (CH(OH))3CH(OH)CH2NH3 +), δ 3.86−3.90 (m, 1H, HOCH2(CH(OH))3CH(OH)CH2NH3 +).
13C−NMR (D2O 100MHz): δ 23.2 (CH3COO−), δ 41.6 (HOCH2(CH(OH))3CH(OH)CH2NH3 +), δ 62.6 (HOCH2(CH(OH))3CH(OH)CH2NH3 +), δ 68.9−70.8 (HOCH2(CH(OH))3 CH(OH)CH2NH3 +), δ 181.4 (CH3 COO−).
<実施例15> 化合物15
FT−IR(KBr):3234cm−1:O−H伸縮振動 2926cm−1:C−H伸縮振動 1572cm−1:COO−伸縮振動
1H−NMR (D2O 400MHz): δ 1.14 (m, 3H, CH 3 CH(OH)COO−), δ 2.83−3.02 (m, 2H, HOCH2(CH(OH))3CH(OH)CH 2 NH3 +), δ 3.45−3.66 (m, 5H, HOCH 2 (CH(OH))3CH(OH)CH2NH3 +), δ 3.81−3.85 (m, 1H, HOCH2(CH(OH))3CH(OH)CH2NH3 +), δ 3.90−3.95 (m, 1H, CH3CH(OH)COO−).
13C−NMR (D2O 100MHz): δ 20.1 (CH3CH(OH)COO−), δ 41.7 (HOCH2(CH(OH))3CH(OH)CH2NH3 +), δ 62.6 (HOCH2(CH(OH))3CH(OH)CH2NH3 +), δ 68.4 (CH3 CH(OH)COO−), δ 68.9−70.9 (HOCH2(CH(OH))3 CH(OH)CH2NH3 +), δ 182.5 (CH3CH(OH)COO−).
<実施例16> 化合物16
FT−IR(KBr):3177cm−1:O−H伸縮振動 2925cm−1:C−H伸縮振動 1709cm−1:COOH伸縮振動 1551cm−1:COO−伸縮振動
1H−NMR (D2O 400MHz): δ 2.42 (s, 4H, HOOCCH 2 CH 2 COO−), δ 2.89−3.08 (m, 2H, HOCH2(CH(OH))3CH(OH)CH 2 NH3 +), δ 3.46−3.67 (m, 5H, HOCH 2 (CH(OH))3CH(OH)CH2NH3 +), δ 3.85−3.89 (m, 1H, HOCH2(CH(OH))3CH(OH)CH2NH3 +).
13C−NMR (D2O 100MHz): δ 31.2 (HOOCCH2 CH2COO−), δ 41.6 (HOCH2(CH(OH))3CH(OH)CH2NH3 +), δ 62.6 (HOCH2(CH(OH))3CH(OH)CH2NH3 +), δ 68.9−70.8 (HOCH2(CH(OH))3 CH(OH)CH2NH3 +), δ 179.6 (HOOCCH2CH2 COO−).
<実施例17> 化合物17
FT−IR(KBr):3226cm−1:O−H伸縮振動 2931cm−1:C−H伸縮振動 1711cm−1:COOH伸縮振動 1575cm−1:COO−伸縮振動
1H−NMR (D2O 400MHz): δ 2.66−2.83 (m, 4H, HOOCCH 2 C(OH)(COO−)CH 2 COOH), δ 2.90−3.10 (m, 2H, HOCH2(CH(OH))3CH(OH)CH 2 NH3 +), δ 3.48−3.68 (m, 5H, HOCH 2 (CH(OH))3CH(OH)CH2NH3 +), δ 3.86−3.90 (m, 1H, HOCH2(CH(OH))3CH(OH)CH2NH3 +).
13C−NMR (D2O 100MHz): δ 41.7 (HOCH2(CH(OH))3CH(OH)CH2NH3 +), δ 43.6 (HOOCCH2C(OH)(COO−)CH2COOH), δ 62.6 (HOCH2(CH(OH))3CH(OH)CH2NH3 +), δ 68.9−70.8 (HOCH2(CH(OH))3 CH(OH)CH2NH3 +), δ 73.8 (HOOCCH2 C(OH)(COO−)CH2COOH), δ 174.6 (HOOCCH2C(OH)(COO−)CH2 COOH), δ 178.6 (HOOCCH2C(OH)(COO−)CH2COOH).
<実施例18> 化合物18
FT−IR(KBr):3174cm−1:O−H伸縮振動 2924cm−1:C−H伸縮振動 1577cm−1:COO−伸縮振動
1H−NMR (D2O 400MHz): δ 2.89−3.09 (m, 2H, HOCH2(CH(OH))3CH(OH)CH 2 NH3 +), δ 3.20 (s, 3H, CH 3 OCH2COO−), δ 3.48−3.69 (m, 5H, HOCH 2 (CH(OH))3CH(OH)CH2NH3 +), δ 3.72 (s, 2H, CH3OCH 2 COO−), δ 3.86−3.90 (m, 1H, HOCH2(CH(OH))3CH(OH)CH2NH3 +).
13C−NMR (D2O 100MHz): δ 41.6 (HOCH2(CH(OH))3CH(OH)CH2NH3 +), δ 58.0 (CH3OCH2COO−), δ 62.6 (HOCH2(CH(OH))3CH(OH)CH2NH3 +), δ 69.0−70.8 (HOCH2(CH(OH))3 CH(OH)CH2NH3 +), δ 71.1 (CH3OCH2COO−), δ 178.0 (CH3OCH2 COO−).
<実施例19> 化合物19
FT−IR(KBr):3388cm−1:O−H伸縮振動 2959cm−1:C−H伸縮振動
1H−NMR (D2O 400MHz): δ 2.71 (s, 3H, CH 3 SO3 −), δ 2.95−3.15 (m, 2H, HOCH2(CH(OH))3CH(OH)CH 2 NH3 +), δ 3.53−3.73 (m, 5H, HOCH 2 (CH(OH))3CH(OH)CH2NH3 +), δ 3.90−3.96 (m, 1H, HOCH2(CH(OH))3CH(OH)CH2NH3 +).
13C−NMR (D2O 100MHz): δ 38.5 (CH3SO3 −), δ 41.7 (HOCH2(CH(OH))3CH(OH)CH2NH3 +), δ 62.7 (HOCH2(CH(OH))3CH(OH)CH2NH3 +), δ 68.9−70.9 (HOCH2(CH(OH))3 CH(OH)CH2NH3 +).
<実施例20> 化合物20
FT-IR(KBr):3464cm-1:O-H伸縮振動 2920cm-1:C-H伸縮振動 1570cm-1:COO-伸縮振動
1H-NMR (D2O 400MHz): δ 1.30 (m, 3H, CH 3 CH(OH)COO−),δ3.07 (s, 9H, CH 3 N+), δ 3.38 (m, 2H, CH 2 N+), δ 3.92 (m, 2H, N+CH2CH 2 OH), δ 3.96 (m, 1H, CH3CH).
13C-NMR (D2O 100MHz): δ 20.1 (CH3CH(OH)COO−), δ53.9 (CH3N+), δ 55.6 (CH2N+), δ 68.4 (N+CH2 CH2OH), δ 72.8 (CH3 CH(OH)COO−), δ 182.3 (CH3CH(OH)COO−).
<実施例21> 化合物21
FT−IR(KBr):3177cm−1:O−H伸縮振動 2925cm−1:C−H伸縮振動 1709cm−1:COOH伸縮振動 1551cm−1:COO−伸縮振動
1H-NMR (D2O 400MHz): δ 2.43 (s, 4H, HOOCCH 2 CH 2 COO−), δ3.07 (s, 9H, CH 3 N+), δ 3.39 (m, 2H, CH 2 N+), δ 3.93 (m, 2H, N+CH2CH 2 OH).
13C-NMR (D2O 100MHz): δ 30.8 (HOOCCH2 CH2COO−), δ53.9 (CH3N+), δ 55.5 (CH2N+), δ 67.4 (N+CH2 CH2OH), δ 179.1 (HOOCCH2CH2 COO−).
<実施例22> 化合物22
FT-IR(KBr):3464cm-1:O-H伸縮振動 2920cm-1:C-H伸縮振動
1H-NMR (D2O 400MHz): δ 3.08 (s, 9H, CH 3 N+), δ 3.39 (m, 2H, CH 2 N+), δ 3.93 (m, 2H, N+CH2CH 2 OH).
13C-NMR (D2O 100MHz): δ 53.9 (CH3N+), δ 55.6 (CH2N+), δ 67.4 (N+CH2 CH2OH).
<実施例23〜27>
化合物23〜27は、特開2012−31137号公報に記載の方法で合成した。
<実施例23> 化合物23
<比較例2〜5>
化合物29のイオン液体は和光純薬工業(株)、化合物30〜32のイオン液体は関東化学(株)の試薬を用いた。
<比較例2> 化合物29:BMI−BF4
化合物33、34のイオン液体は特表2006−514832号公報に記載の方法に従って合成した。
<比較例6> 化合物33:HOPMI−PF6
和光純薬工業(株)の試薬を用いた。
<比較例9> 化合物36:バッファー
バッファーとして、ウレアーゼ、カタラーゼ保存試験においては、水酸化ナトリウムでpH調製したリン酸二水素カリウムの10mM水溶液(リン酸緩衝液:ウレアーゼ:pH7.5、カタラーゼ:pH7.0)を用いた。また、ヘキソキナーゼ、アルギン酸リアーゼ保存試験においては、塩酸でpH調製したトリスヒドロキシメチルアミノメタンの水溶液(トリス緩衝液:ヘキソキナーゼ:50mM(pH8.5)、アルギン酸リアーゼ:200mM(pH7.0))を用いた。また、シトクロムP450保存試験においては、水酸化ナトリウムでpH7.4に調製したリン酸二水素カリウムの100mM水溶液を用いた。
<比較例10> 化合物37:グリセリン水溶液
グリセリン(和光純薬工業(株))を水に溶解して10mg/mLに調製した。
<比較例11> 化合物38:グルコース水溶液
D(+)−グルコース(関東化学(株))を水に溶解して10mg/mLに調製した。
<比較例12> 化合物39:ウシ血清アルブミン水溶液
アルブミン(牛由来、一般グレード、pH5.2:ナカライテスク(株))を水に溶解して10mg/mLに調製した。
<比較例13> 化合物40:リシン水溶液
L(+)−リシン(和光純薬工業(株))を水に溶解して10mg/mLに調製した。
<比較例14> 化合物41:リシン、ウシ血清アルブミン水溶液
L(+)−リシン(和光純薬工業(株))とアルブミン(牛由来、一般グレード、pH5.2:ナカライテスク(株))を重量比54:46の混合物を水で10mg/mL水溶液に調製した。
<比較例15> 化合物42:アルギニン水溶液
L(+)−アルギニン(和光純薬工業(株))を水に溶解して10mg/mLに調製した。
<比較例16> 化合物43:20%グリセリン溶液
グリセリン(和光純薬工業(株))をpH7.4に調製したリン酸二水素カリウムの100mM水溶液に溶解して、20%溶液に調製した。
1.凝固点の測定
化合物1〜42をスクリュー管に添加して、−5℃及び−10℃に設定した低温恒温器に24時間放置し、性状(液体、固体)を確認して凝固点を測定した(表1〜3)。
2.酵素溶解試験
化合物1〜35(実施例1〜27、比較例1〜8)のウレアーゼ、α−アミラーゼ、カタラーゼ、クエン酸シンターゼ、アルギン酸リアーゼ、ホスホグルコースイソメラーゼ、アセチルCoAシンセターゼ、ヘキソキナーゼ、シトクロムP450に対する溶解濃度を測定した。表1〜3に示す含水率の化合物1〜35に、室温(25℃)で各酵素を所定濃度添加し、混合後、溶解を目視にて判別した(表1〜3)。
表4〜32中の化合物に、それぞれウレアーゼ、カタラーゼ、α−アミラーゼ、クエン酸シンターゼ、ヘキソキナーゼ、アルギン酸リアーゼ、ホスホグルコースイソメラーゼ、アセチルCoAシンセターゼを、表4〜31記載の酵素濃度で溶解して、一般的に、酵素を溶解、活性を保持する温度より高い25℃及び、更に高温条件、また安定性の促進試験として40℃の条件に設定した恒温器に放置した。また、安定性の特に低いシトクロムP450は、表32記載の酵素濃度で溶解して、一般的にシトクロムP450の活性を保持する温度より高い3℃の条件に設定した恒温器に放置した。
<加水分解酵素:ウレアーゼの活性測定:表4〜9>
ウレアーゼの活性は、ウレアーゼの酵素反応によって、尿素から分解生成するアンモニウムイオンをインドフェノール法によって定量して測定した。
<酸化還元酵素:カタラーゼの活性測定:表10〜15>
カタラーゼは過酸化水素を酸素と水素に分解する酵素である。その活性は、カタラーゼの反応基質である過酸化水素量を定量して測定した。
<加水分解酵素:アミラーゼの活性測定:表16,17>
アミラーゼはデンプン中のアミロースやアミロペクチンを、単糖類であるブドウ糖や二糖類であるマルトースおよびオリゴ糖に変換する酵素である。その活性は、アミラーゼの反応基質であるでんぷんを定量して測定した。
<転移酵素:クエン酸シンターゼの活性測定:表18,19>
クエン酸シンターゼはオキサロ酢酸+アセチル補酵素A+H2O → クエン酸+補酵素A+H+の反応に寄与する酵素である。その活性は、反応によって生成する補酵素Aを、DTNB(5,5'−ジチオビス−2−ニトロ安息香酸)と反応して得られる生成物を定量して測定した。
※モル吸光係数13600 L/(M・cm)
なお、酵素活性保持率の基準となる酵素活性の値は、次のように算出した。適正温度で保存したクエン酸シンターゼをバッファー(pH8.0に調製した1Mトリス緩衝液)に溶解して酵素濃度0.1mg/mLの酵素溶液を調製した。調製後、直ちにその溶液を、上記と同様に、酵素量が0.1mgとなるように基質溶液に加え、酵素反応を行った後、上記と同様の方法で算出した生成物量を基準として、酵素活性保持率を算出した。
<転移酵素:ヘキソキナーゼの活性測定:表20〜23>
ヘキソキナーゼはATPの存在下、グルコースなどのヘキソースをリン酸化して、ヘキソース−6−リン酸とする反応に寄与する酵素である。その活性は、ヘキソキナーゼが分解したグルコースが、ATPと反応して生じたNADPH(ニコチンアミドアデニンジヌクレオチドリン酸還元型)を定量して測定した。
※NADPHの340nmにおけるミリモル分子吸光係数(L/(mM・cm))
なお、酵素活性保持率の基準となる酵素活性の値は、次のように算出した。適正温度で保存したヘキソキナーゼをバッファー(pH8.5に調製した50mMトリス緩衝液)に溶解して酵素濃度10.0mg/mLの酵素溶液を調製した。調製後、直ちにその溶液を、上記と同様に、酵素量が0.05mgとなるように基質溶液に加え、酵素反応を行った後、上記と同様の方法で算出したNADPH量を基準として、酵素活性保持率を算出した。
<脱離酵素:アルギン酸リアーゼの活性測定:表24〜27>
アルギン酸リアーゼはアルギン酸を分解反応に寄与する酵素である。その活性は、アルギン酸リアーゼがアルギン酸を分解することにより生成する2重結合を有する糖が、235nmに特異的な吸光度変化を示すことから、この生成物を定量して測定した。
<異性化酵素:ホスホグルコースイソメラーゼの活性測定:表28,29>
ホスホグルコースイソメラーゼはグルコースをフルクトースへ変換する酵素である。その活性は、ホスホグルコースイソメラーゼによって生成したフルクトース量を定量して測定した。
(pH7.2の200mMリン酸緩衝液90mL、100mM 硫酸マグネシウム
溶液 10mLにグルコース溶解して作成)
B:200mMリン酸緩衝液(pH7.2)
C:500mM過塩素酸水溶液
D:1.5%システイン水溶液
E:70% 硫酸水溶液
F:0.12%カルバゾール−エタノール溶液
続いて、10mLのスクリュー管にAを1.0mL採取して基質溶液とし、60℃で約30分間予備加温した。次に、表28,29中に記載の設定濃度及び温度で、所定期間放置したサンプル(化合物3〜6,10,11,13,18,22,23,27)を、酵素量が0.03mgとなるように上記の基質溶液に添加し、Bを1.0mL加え、60℃で60分間反応させた。反応後、Cを2.0mL加えて冷却し、50mLにメスアップした。そして、この溶液を1.0mL採取して、Dを0.2mL、Eを6.0mL加えて振り混ぜ、溶液を冷却後、Fを0.2mL加えて60℃で10分間反応させた。
<合成酵素:アセチルCoAシンセターゼの活性測定:表30,31>
アセチルCoAシンセターゼはATPのエネルギーを使い、補酵素A(CoA)と酢酸からアセチルCoAを合成する反応を触媒する酵素である。その活性は、アセチルCoAシンセターゼの反応基質である酢酸を定量して測定した。
<酸化還元酵素:シトクロムP450の活性測定:表32>
シトクロムP450の活性は、シトクロムP450の酵素反応によって基質であるテストステロンから生成する6β−ヒドロキシテストステロンをHPLCによって定量して測定した。
4.−10℃保存試験
カタラーゼを本発明のイオン液体(化合物4,10,15:実施例28,29,30)に50mg/mL、従来の安定化剤を溶解した水溶液(化合物36〜41:比較例17〜22)に20mg/mLの濃度に溶解して、−10℃で設定した低温恒温器に24時間放置した。本発明のイオン液体溶液は液性を保持したのに対して、化合物36〜41の水溶液は凍結した。その後、25℃の恒温器に放置して昇温して(化合物36〜41の水溶液は溶解)、上記と同様にカタラーゼの活性を測定した。
5.低濃度保存試験
サンプル(化合物4〜6,10,18,22,23,27,29,35〜40,42)に濃度が10μg/mL、10ng/mLとなるようにウレアーゼを溶解して、25℃及び、40℃に設定した恒温器に放置し、180日後、上記と同様にウレアーゼの活性を測定した。
6.無水イオン液体保存性試験
無水イオン液体中のウレアーゼの保存性試験を、次のように実施した。まず、サンプル(化合物1〜6,8〜11,13,15,18,20,23,24,27,29,33〜35)をスクリュー管に入れ減圧脱水して無水イオン液体を作成し、そこに、表38,39中に記載の設定濃度となるようにウレアーゼを加えて溶解した。その後、それぞれのスクリュー管に水分が混入しないようにスクリュー管内を窒素置換し、密閉した。そして、25℃及び40℃に設定した恒温器中に放置し、上記と同様の方法でウレアーゼの活性を測定した。
Claims (11)
- 生体触媒の活性を保持した状態で使用するための生体触媒用溶媒であって、下記式(I):
- 式(I)のnが1〜3の整数である請求項1に記載の生体触媒溶液。
- 前記生体触媒用溶媒は、生体触媒の活性を保持した状態で保存することが可能な生体触媒用溶媒である請求項2に記載の生体触媒溶液。
- イオン液体のアニオンが、ハロゲン系アニオン、硫黄系アニオン、リン系アニオン、シアン系アニオン、ホウ素系アニオン、フッ素系アニオン、窒素酸化物系アニオン、及びカルボン酸アニオンから選ばれる少なくとも1種であり、
生体触媒が酵素である請求項2に記載の生体触媒溶液。 - イオン液体のアニオンが、ハロゲン系アニオン、リン系アニオン、シアン系アニオン、ホウ素系アニオン、フッ素系アニオン、窒素酸化物系アニオン、及びカルボン酸アニオンから選ばれる少なくとも1種であり、
生体触媒が酵素である請求項2に記載の生体触媒溶液。 - イオン液体のアニオンが、カルボン酸アニオン、スルホン酸アニオン、及びリン酸アニオンから選ばれる少なくとも1種であり、
生体触媒が酵素である請求項4に記載の生体触媒溶液。 - イオン液体のアニオンがカルボン酸アニオンであり、
生体触媒が酵素である請求項4に記載の生体触媒溶液。 - イオン液体のアニオンがヒドロキシカルボン酸アニオンであり、
生体触媒が酵素である請求項4に記載の生体触媒溶液。 - 前記生体触媒用溶媒は、ウレアーゼを30.0〜50.0mg/mLで溶解したときに温度25℃で保存した場合、30日後のウレアーゼの触媒活性保持率が90%以上である請求項1から8のいずれかに記載の生体触媒溶液。
- 以下の工程を含む、生体触媒用溶媒を使用する方法:
請求項1から9のいずれかに記載の、生体触媒用溶媒と生体触媒とを含む生体触媒溶液を調製する工程;及び、
前記生体触媒溶液を調製した後、前記生体触媒を反応触媒に用いて、この生体触媒が特異性を持つ生化学反応に供する工程。 - 以下の工程を含む、生体触媒用溶媒を使用する方法:
請求項1から9のいずれかに記載の、生体触媒用溶媒と生体触媒とを含む生体触媒溶液を調製する工程;
前記生体触媒溶液を調製した後、前記生体触媒溶液を保存する工程;及び、
前記保存した後、前記生体触媒を反応触媒に用いて、この生体触媒が特異性を持つ生化学反応に供する工程。
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