CN103614449A - Resolution method for Se-methylselenocysteine - Google Patents

Resolution method for Se-methylselenocysteine Download PDF

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CN103614449A
CN103614449A CN201310502507.2A CN201310502507A CN103614449A CN 103614449 A CN103614449 A CN 103614449A CN 201310502507 A CN201310502507 A CN 201310502507A CN 103614449 A CN103614449 A CN 103614449A
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methylselenocysteinefrom
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王玲
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Abstract

The invention discloses a resolution method for Se-methylselenocysteine. The resolution method includes subjecting N-acetyl-DL-Se-methylselenocysteine to enzymolysis by using aspergillus oryzae amino-acylase or immobilized aspergillus oryzae enzyme to obtain L-Se-methylselenocysteine and N-acetyl-D-Se-methylselenocysteine and then performing acid hydrolysis to obtain D-Se-methylselenocysteine; or includes subjecting the N-acetyl-DL-Se-methylselenocysteine to an enzymatic reaction by using papain and aniline to obtain aniline N-acetyl-L-Se-methylselenocysteine salt and N-acetyl-D-Se-methylselenocysteine and then performing acid hydrolysis to obtain the D-Se-methylselenocysteine and the L-Se-methylselenocysteine.

Description

The method for splitting of methylselenocysteinefrom
Technical field
The invention belongs to amino acid field, relate to the method for splitting of methylselenocysteinefrom.
Background technology
Selenium is the necessary trace element of human body, has anticancer, anti-cancer, cardioprotection, prevents and treats cataract, Keshan disease and Kaschin-Beck disease, delays senility, separates the functions such as heavy metal poison.Selenium deficiency will cause selenoenzyme activity decreased, and oxygen radical removing is obstructed, biomembrane damage, and a series of body function obstacles such as removing toxic substances and immunocyte decline, thus cause various diseases to occur.Supplement selenium element is that prevention lacks the effective ways that selenium disease occurs.At present, domestic selenium component extender has Sodium Selenite, sodium selenate, selenocarrageenan, selenomethionine and methylselenocysteinefrom etc.Methylselenocysteinefrom is a kind of containing selenium natural amino acid, be present in the plants such as garlic and onion, it has supplement selenium element, anti-curing cancers, anti-oxidant, anti-ageing, control cardiovascular and cerebrovascular diseases, separates the effects such as heavy metal poison, can be applicable to the aspects such as medicine and nutritive health-care.Methylselenocysteinefrom as selenium component extender is generally L-type, and natural methylselenocysteinefrom is generally L-type, and the methylselenocysteinefrom of chemosynthesis is generally D, L mixed type.For preparing optical purity L-type methylselenocysteinefrom and D type methylselenocysteinefrom, the invention provides the method for splitting of methylselenocysteinefrom, the method is easy to operate, cost is lower, be applicable to preparation of industrialization optical purity L-type and D type methylselenocysteinefrom.
Summary of the invention
The present invention includes following content:
1, the fractionation of DL-methylselenocysteinefrom
(1) Aminoacylase from A.Oryzae Split Method
DL-methylselenocysteinefrom is dissolved in to aqueous sodium hydroxide solution, drips excess acetyl chloride and obtain N-acetyl-DL-methylselenocysteinefrom sodium, then with hydrochloric acid or sulfuric acid acidation, obtain N-acetyl-DL-methylselenocysteinefrom;
The western Se-Methylselenocysteine of N-acetyl-DL-is dissolved in to buffered soln, add Aminoacylase from A.Oryzae, carry out enzyme digestion reaction, after enzymolysis, solution is separated with storng-acid cation exchange resin, and water and ammoniacal liquor wash-out obtain N-acetyl-D-methylselenocysteinefrom and L-methylselenocysteinefrom; By N-acetyl-D-methylselenocysteinefrom strong acid, example hydrochloric acid, Hydrogen bromide, hydroiodic acid HI or sulfuric acid etc., heating hydrolysis is complete, then with ammonia neutralization, obtains D-methylselenocysteinefrom; Described enzyme digestion reaction is to carry out under pH4-10, temperature are the condition of 10-60 ℃.
(2) produce the immobilization aspergillus oryzae cell Split Method of L-Aminoacylase
Adopt ordinary method that the aspergillus oryzae cell that produces L-Aminoacylase is fixed with gelatin-glutaraldehyde or gelatin-formaldehyde, obtain immobilization aspergillus oryzae cell, and dress up column type reactor, allow the solution stream that contains N-acetyl-DL-methylselenocysteinefrom cross immobilization aspergillus oryzae cell column type reactor, collect and split effluent liquid, to split effluent liquid separated with storng-acid cation exchange resin, water and ammoniacal liquor wash-out obtain N-acetyl-D-methylselenocysteinefrom and L-methylselenocysteinefrom; By N-acetyl-D-methylselenocysteinefrom strong acid, example hydrochloric acid, Hydrogen bromide, hydroiodic acid HI or sulfuric acid, heating hydrolysis is complete, then with ammonia neutralization, obtains D-methylselenocysteinefrom; Described resolution reaction is to carry out under pH4-10, temperature are the condition of 10-60 ℃.
(3) papoid Split Method
N-acetyl-DL-methylselenocysteinefrom is dissolved in buffered soln, add aniline or to monomethylaniline, add again papoid, carry out enzymatic reaction, after completion of the reaction, filter, insolubles is that N-acetyl-L-methylselenocysteinefrom aniline or N-acetyl-L-methylselenocysteinefrom are to monomethylaniline, complete with hydrochloric acid or sulfuric acid heating hydrolysis, then with ammonia neutralization, obtain L-methylselenocysteinefrom; Filtrate is containing N-acetyl-D-methylselenocysteinefrom, complete with hydrochloric acid or sulfuric acid heating hydrolysis after concentrating under reduced pressure, then with ammonia neutralization, obtains D-methylselenocysteinefrom; Described enzymatic reaction is to carry out under 20-70 ℃ of condition in pH3-9, temperature.
Embodiment
Below in conjunction with embodiment, the present invention is described in further detail, but should understands the non-scope that only limits to these embodiment of scope of the present invention.
Embodiment 1:
Aminoacylase from A.Oryzae splits DL-methylselenocysteinefrom:
0.1mol DL-methylselenocysteinefrom is dissolved in to 200ml20% aqueous sodium hydroxide solution, under ice-water bath, slowly drip 0.15mol Acetyl Chloride 98Min., then be warming up to 25 ℃ of reaction 6h, with triketohydrindene hydrate, detect to without amino acid reaction, with concentrated hydrochloric acid, regulate pH to 1-2, then be extracted with ethyl acetate, evaporated under reduced pressure solvent after organic phase is merged, obtains 20.1 grams of N-acetyl-DL-methylselenocysteinefroms, yield 89.73%.
0.1mol N-acetyl-DL-methylselenocysteinefrom is dissolved in to the HAc-NaAc buffered soln of 500ml pH4; add 22.4mg Aminoacylase from A.Oryzae; control 10 ℃ of temperature; react after approximately 12 hours solution is made to enzyme denaturation precipitation in 90 ℃ of heating; filter; filtrate is separated with storng-acid cation exchange resin, water and 5% ammoniacal liquor wash-out.By after water elution liquid evaporated under reduced pressure, obtain N-acetyl-D-methylselenocysteinefrom, be dissolved in 200 milliliters of concentrated hydrochloric acids, complete in 95 ℃ of hydrolysis in 3 hours that reflux, with ammonia neutralization, evaporated under reduced pressure solvent obtains solid, with dissolve with methanol, elimination insolubles, concentrates to obtain D-methylselenocysteinefrom 7.5g, yield 82.42%.By after 5% ammoniacal liquor elutriant evaporated under reduced pressure, obtain 7.7 grams of L-methylselenocysteinefroms, yield 84.62%.
Embodiment 2:
Aminoacylase from A.Oryzae splits DL-methylselenocysteinefrom:
0.1mol DL-methylselenocysteinefrom is dissolved in to 200ml20% aqueous sodium hydroxide solution, under ice-water bath, slowly drip 0.15mol Acetyl Chloride 98Min., then be warming up to 45 ℃ of reaction 4h, with triketohydrindene hydrate, detect to without amino acid reaction, with concentrated hydrochloric acid, regulate pH to 1-2, then be extracted with ethyl acetate, evaporated under reduced pressure solvent after organic phase is merged, obtains 20.3 grams of N-acetyl-DL-methylselenocysteinefroms, yield 90.62%.
0.1mol N-acetyl-DL-methylselenocysteinefrom is dissolved in to the KH of 500ml pH7 2pO 4-Na 2hPO 4buffered soln, adds 0.224g Aminoacylase from A.Oryzae, controls 40 ℃ of temperature, reacts after approximately 10 hours solution is made to enzyme denaturation precipitation in 90 ℃ of heating, filters, and filtrate is separated with storng-acid cation exchange resin, water and 5% ammoniacal liquor wash-out.By after water elution liquid evaporated under reduced pressure, obtain N-acetyl-D-methylselenocysteinefrom, be dissolved in 200 milliliter of 30% Hydrogen bromide, complete in 95 ℃ of hydrolysis in 3 hours that reflux, with ammonia neutralization, evaporated under reduced pressure solvent obtains solid, with dissolve with methanol, elimination insolubles, concentrates to obtain D-methylselenocysteinefrom 7.8g, yield 85.71%.By after 5% ammoniacal liquor elutriant evaporated under reduced pressure, obtain 8.0 grams of L-methylselenocysteinefroms, yield 87.91%.
Embodiment 3:
Aminoacylase from A.Oryzae splits DL-methylselenocysteinefrom:
0.1mol DL-methylselenocysteinefrom is dissolved in to 200ml20% aqueous sodium hydroxide solution, under ice-water bath, slowly drip 0.15mol Acetyl Chloride 98Min., then be warming up to 65 ℃ of reaction 3h, with triketohydrindene hydrate, detect to without amino acid reaction, with concentrated hydrochloric acid, regulate pH to 1-2, then be extracted with ethyl acetate, evaporated under reduced pressure solvent after organic phase is merged, obtains 19.0 grams of N-acetyl-DL-methylselenocysteinefroms, yield 84.82%.
0.1mol N-acetyl-DL-methylselenocysteinefrom is dissolved in to the NaHCO of 500ml pH10 3-NaHCO 3buffered soln, adds 2.24g Aminoacylase from A.Oryzae, controls temperature 60 C, reacts after approximately 8 hours solution is made to enzyme denaturation precipitation in 90 ℃ of heating, filters, and filtrate is separated with storng-acid cation exchange resin, water and 5% ammoniacal liquor wash-out.By after water elution liquid evaporated under reduced pressure, obtain N-acetyl-D-methylselenocysteinefrom, be dissolved in 200 milliliter of 30% hydroiodic acid HI, complete in 95 ℃ of hydrolysis in 3 hours that reflux, with ammonia neutralization, evaporated under reduced pressure solvent obtains solid, with dissolve with methanol, elimination insolubles, concentrates to obtain D-methylselenocysteinefrom 8.1g, yield 89.01%.By after 5% ammoniacal liquor elutriant evaporated under reduced pressure, obtain 8.4 grams of L-methylselenocysteinefroms, yield 92.31%.
Embodiment 4:
Aminoacylase from A.Oryzae splits DL-methylselenocysteinefrom:
0.1mol N-acetyl-DL-methylselenocysteinefrom is dissolved in to the KH of 500ml pH7 2pO 4-Na 2hPO 4buffered soln, adds 0.224g Aminoacylase from A.Oryzae, controls 40 ℃ of temperature, reacts after approximately 10 hours solution is made to enzyme denaturation precipitation in 90 ℃ of heating, filters, and filtrate is separated with storng-acid cation exchange resin, water and 5% ammoniacal liquor wash-out.By after water elution liquid evaporated under reduced pressure, obtain N-acetyl-D-methylselenocysteinefrom, be dissolved in 200 milliliter of 50% sulfuric acid, complete in 95 ℃ of hydrolysis in 3 hours that reflux, with ammonia neutralization, concentrating under reduced pressure obtains solid, with dissolve with methanol, elimination insolubles, concentrates to obtain D-methylselenocysteinefrom 6.8g, yield 74.72%.By after 5% ammoniacal liquor elutriant evaporated under reduced pressure, obtain 7.4 grams of L-methylselenocysteinefroms, yield 81.34%.
Embodiment 5:
The immobilization aspergillus oryzae cell that produces L-Aminoacylase splits DL-methylselenocysteinefrom:
Adopt ordinary method that the aspergillus oryzae cell that produces L-Aminoacylase is fixed with gelatin-glutaraldehyde or gelatin-formaldehyde, must produce the immobilization aspergillus oryzae cell of L-Aminoacylase, and immobilization aspergillus oryzae cell is dressed up to column type reactor.0.1mol N-acetyl-DL-methylselenocysteinefrom is dissolved in to the HAc-NaAc buffered soln of 500ml pH4, control 10 ℃ of temperature, slowly, by immobilization aspergillus oryzae cell column type reactor, split liquid separated with storng-acid cation exchange resin, water and 5% ammoniacal liquor wash-out.By after water elution liquid evaporated under reduced pressure, obtain N-acetyl-D-methylselenocysteinefrom, be dissolved in 200 milliliters of concentrated hydrochloric acids, complete in 95 ℃ of hydrolysis in 3 hours that reflux, with ammonia neutralization, evaporated under reduced pressure solvent obtains solid, with dissolve with methanol, elimination insolubles, concentrates to obtain D-methylselenocysteinefrom 7.8g, yield 85.71%.By after 5% ammoniacal liquor elutriant evaporated under reduced pressure, obtain 8.0 grams of L-methylselenocysteinefroms, yield 87.91%.
Embodiment 6:
The immobilization aspergillus oryzae cell that produces L-Aminoacylase splits DL-methylselenocysteinefrom:
0.1mol N-acetyl-DL-methylselenocysteinefrom is dissolved in to the KH of 500ml pH7 2pO 4-Na 2hPO 4buffered soln, controls 40 ℃ of temperature, slowly by immobilization aspergillus oryzae cell column type reactor, splits liquid separated with storng-acid cation exchange resin, water and 5% ammoniacal liquor wash-out.By after water elution liquid evaporated under reduced pressure, obtain N-acetyl-D-methylselenocysteinefrom, be dissolved in 200 milliliter of 30% Hydrogen bromide, complete in 95 ℃ of hydrolysis in 3 hours that reflux, with ammonia neutralization, evaporated under reduced pressure solvent obtains solid, with dissolve with methanol, elimination insolubles, concentrated D-methylselenocysteinefrom 7.5g, the yield 82.42% of separating out.By after 5% ammoniacal liquor elutriant evaporated under reduced pressure, obtain 8.4 grams of L-methylselenocysteinefroms, yield 92.31%.
Embodiment 7:
The immobilization aspergillus oryzae cell that produces L-Aminoacylase splits DL-methylselenocysteinefrom:
0.1mol N-acetyl-DL-methylselenocysteinefrom is dissolved in to the NaHCO of 500ml pH10 3-NaHCO 3buffered soln, controls temperature 60 C, slowly by immobilization aspergillus oryzae cell column type reactor, splits liquid separated with storng-acid cation exchange resin, water and 5% ammoniacal liquor wash-out.By after water elution liquid evaporated under reduced pressure, obtain N-acetyl-D-methylselenocysteinefrom, be dissolved in 200 milliliter of 30% hydroiodic acid HI, complete in 95 ℃ of hydrolysis in 3 hours that reflux, with ammonia neutralization, evaporated under reduced pressure solvent obtains solid, with dissolve with methanol, elimination insolubles, concentrated D-methylselenocysteinefrom 6.7g, the yield 73.63% of separating out.By after 5% ammoniacal liquor elutriant evaporated under reduced pressure, obtain 7.0 grams of L-methylselenocysteinefroms, yield 76.92%.
Embodiment 8:
The immobilization aspergillus oryzae cell that produces L-Aminoacylase splits DL-methylselenocysteinefrom:
0.1mol N-acetyl-DL-methylselenocysteinefrom is dissolved in to the KH of 500ml pH7 2pO 4-Na 2hPO 4buffered soln, controls 40 ℃ of temperature, slowly by immobilization aspergillus oryzae cell column type reactor, splits liquid separated with storng-acid cation exchange resin, water and 5% ammoniacal liquor wash-out.By after water elution liquid evaporated under reduced pressure, obtain N-acetyl-D-methylselenocysteinefrom, be dissolved in 200 milliliter of 50% sulfuric acid, complete in 95 ℃ of hydrolysis in 3 hours that reflux, with ammonia neutralization, evaporated under reduced pressure solvent obtains solid, with dissolve with methanol, elimination insolubles, concentrated D-methylselenocysteinefrom 6.3g, the yield 69.23% of separating out.By after 5% ammoniacal liquor elutriant evaporated under reduced pressure, obtain 6.4 grams of L-methylselenocysteinefroms, yield 70.33%.
Embodiment 9:
Papoid splits DL-methylselenocysteinefrom:
0.1mol N-acetyl-DL-methylselenocysteinefrom is dissolved in the hydrochloric acid soln of 500ml pH3, adds 0.1mol aniline and 22.4mg papoid, control 20 ℃ of temperature, enzymatic reaction 10h, after completion of the reaction, filter, the insolubles of filtration with the hydrolysis of 200ml concentrated hydrochloric acid reflux completely, then use ammonia neutralization, evaporated under reduced pressure solvent obtains solid, with dissolve with methanol, and elimination insolubles, concentrate to obtain L-methylselenocysteinefrom 6.7g, yield 73.63%.After filtrate decompression is concentrated, add 200ml concentrated hydrochloric acid, reflux hydrolysis completely, is then used ammonia neutralization, and evaporated under reduced pressure solvent obtains solid, with dissolve with methanol, elimination insolubles, concentrates to obtain D-methylselenocysteinefrom 6.9g, yield 75.82%.
Embodiment 10:
Papoid splits DL-methylselenocysteinefrom:
0.1mol N-acetyl-DL-methylselenocysteinefrom is dissolved in the HAc-NaAc buffered soln of 500ml pH5, adds 0.2mol aniline and 0.224g papoid, control temperature 50 C, enzymatic reaction 8h, after completion of the reaction, filter, the insolubles of filtration with the hydrolysis of 200ml50% sulfuric acid reflux completely, then use ammonia neutralization, concentrating under reduced pressure obtains solid, with dissolve with methanol, and elimination insolubles, concentrate to obtain L-methylselenocysteinefrom 7.3g, yield 80.22%.After filtrate decompression is concentrated, add 200ml50% sulfuric acid, reflux hydrolysis completely, is then used ammonia neutralization, and concentrating under reduced pressure obtains solid, with dissolve with methanol, elimination insolubles, concentrates to obtain D-methylselenocysteinefrom 8.4g, yield 92.31%.
Embodiment 11:
Papoid splits DL-methylselenocysteinefrom:
0.1mol N-acetyl-DL-methylselenocysteinefrom is dissolved in to the NaHCO of 500ml pH9 3-NaHCO 3in buffered soln, add 0.4mol aniline and 2.24g papoid, control temperature 70 C, enzymatic reaction 8h, after completion of the reaction, filter, the insolubles of filtration with the hydrolysis of 200ml concentrated hydrochloric acid reflux completely, then use ammonia neutralization, evaporated under reduced pressure solvent obtains solid, with dissolve with methanol, and elimination insolubles, concentrate to obtain L-methylselenocysteinefrom 6.0g, yield 65.93%.After filtrate decompression is concentrated, add 200ml concentrated hydrochloric acid, reflux hydrolysis completely, is then used ammonia neutralization, and evaporated under reduced pressure solvent obtains solid, with dissolve with methanol, elimination insolubles, concentrates to obtain D-methylselenocysteinefrom 5.8g, yield 63.74%.
Embodiment 12:
Papoid splits DL-methylselenocysteinefrom:
0.1mol N-acetyl-DL-methylselenocysteinefrom is dissolved in the hydrochloric acid soln of 500ml pH3, adds 0.1mol to monomethylaniline and 22.4mg papoid, control 20 ℃ of temperature, enzymatic reaction 10h, after completion of the reaction, filter, the insolubles of filtration with the hydrolysis of 200ml concentrated hydrochloric acid reflux completely, then use ammonia neutralization, evaporated under reduced pressure solvent obtains solid, with dissolve with methanol, and elimination insolubles, concentrate to obtain L-methylselenocysteinefrom 7.9g, yield 86.81%.After filtrate decompression is concentrated, add 200ml concentrated hydrochloric acid, reflux hydrolysis completely, is then used ammonia neutralization, and evaporated under reduced pressure solvent obtains solid, with dissolve with methanol, elimination insolubles, concentrates to obtain D-methylselenocysteinefrom 7.1g, yield 78.02%.
Embodiment 13:
Papoid splits DL-methylselenocysteinefrom:
0.1mol N-acetyl-DL-methylselenocysteinefrom is dissolved in the HAc-NaAc buffered soln of 500ml pH5, adds 0.2mol to monomethylaniline and 0.224g papoid, control temperature 50 C, enzymatic reaction 8h, after completion of the reaction, filter, the insolubles of filtration with the hydrolysis of 200ml concentrated hydrochloric acid reflux completely, then use ammonia neutralization, evaporated under reduced pressure solvent obtains solid, with dissolve with methanol, and elimination insolubles, concentrate to obtain L-methylselenocysteinefrom 6.7g, yield 73.63%.After filtrate decompression is concentrated, add 200ml concentrated hydrochloric acid, reflux hydrolysis completely, is then used ammonia neutralization, and evaporated under reduced pressure solvent obtains solid, with dissolve with methanol, elimination insolubles, concentrates to obtain D-methylselenocysteinefrom 6.1g, yield 67.03%.
Embodiment 14:
Papoid splits DL-methylselenocysteinefrom:
0.1mol N-acetyl-DL-methylselenocysteinefrom is dissolved in to the NaHCO of 500ml pH9 3-NaHCO 3in buffered soln, add 0.4mol to monomethylaniline and 2.24g papoid, control temperature 70 C, enzymatic reaction 8h, after completion of the reaction, filter, the insolubles of filtration with the hydrolysis of 200ml concentrated hydrochloric acid reflux completely, then use ammonia neutralization, evaporated under reduced pressure solvent obtains solid, with dissolve with methanol, and elimination insolubles, concentrate to obtain L-methylselenocysteinefrom 5.4g, yield 59.34%.After filtrate decompression is concentrated, add 200ml concentrated hydrochloric acid, reflux hydrolysis completely, is then used ammonia neutralization, and evaporated under reduced pressure solvent obtains solid, with dissolve with methanol, elimination insolubles, concentrates to obtain D-methylselenocysteinefrom 5.1g, yield 56.04%.
Embodiment 15:
Papoid splits DL-methylselenocysteinefrom:
0.1mol N-acetyl-DL-methylselenocysteinefrom is dissolved in the HAc-NaAc buffered soln of 500ml pH5, adds 0.2mol to monomethylaniline and 0.224g papoid, control temperature 50 C, enzymatic reaction 8h, after completion of the reaction, filter, the insolubles of filtration with the hydrolysis of 200ml50% sulfuric acid reflux completely, then use ammonia neutralization, concentrating under reduced pressure obtains solid, with dissolve with methanol, and elimination insolubles, concentrate to obtain L-methylselenocysteinefrom 5.7g, yield 62.64%.After filtrate decompression is concentrated, add 200ml50% sulfuric acid, reflux hydrolysis completely, is then used ammonia neutralization, and concentrating under reduced pressure obtains solid, with dissolve with methanol, elimination insolubles, concentrates to obtain D-methylselenocysteinefrom 5.1g, yield 56.04%.

Claims (3)

1. the method for splitting of methylselenocysteinefrom, is characterized in that comprising the following steps:
DL-methylselenocysteinefrom is dissolved in to aqueous sodium hydroxide solution, drips excess acetyl chloride and obtain N-acetyl-DL-methylselenocysteinefrom sodium, then with hydrochloric acid or sulfuric acid acidation, obtain N-acetyl-DL-methylselenocysteinefrom;
N-acetyl-DL-methylselenocysteinefrom is dissolved in to buffered soln, add Aminoacylase from A.Oryzae, carry out enzyme digestion reaction, after enzymolysis, solution is separated with storng-acid cation exchange resin, and water and ammoniacal liquor wash-out obtain N-acetyl-D-methylselenocysteinefrom and L-methylselenocysteinefrom; By N-acetyl-D-methylselenocysteinefrom strong acid, example hydrochloric acid, Hydrogen bromide, hydroiodic acid HI or sulfuric acid etc., heating hydrolysis is complete, then with ammonia neutralization, obtains D-methylselenocysteinefrom; Described enzyme digestion reaction is to carry out under pH4-10, temperature are the condition of 10-60 ℃.
2. the method for splitting of methylselenocysteinefrom, is characterized in that comprising the following steps:
Adopt ordinary method that the aspergillus oryzae cell that produces L-Aminoacylase is fixed with gelatin-glutaraldehyde or gelatin-formaldehyde, must produce the immobilization aspergillus oryzae cell of L-Aminoacylase, and immobilization aspergillus oryzae cell is dressed up to column type reactor, allow the solution stream that contains N-acetyl-DL-methylselenocysteinefrom cross immobilization aspergillus oryzae cell column type reactor, collect and split effluent liquid, to split effluent liquid separated with storng-acid cation exchange resin, water and ammoniacal liquor wash-out obtain N-acetyl-D-methylselenocysteinefrom and L-methylselenocysteinefrom; By N-acetyl-D-methylselenocysteinefrom strong acid, example hydrochloric acid, Hydrogen bromide, hydroiodic acid HI or sulfuric acid, heating hydrolysis is complete, then with ammonia neutralization, obtains D-methylselenocysteinefrom; Described resolution reaction is to carry out under pH4-10, temperature are the condition of 10-60 ℃.
3. the method for splitting of methylselenocysteinefrom, is characterized in that comprising the following steps:
N-acetyl-DL-methylselenocysteinefrom is dissolved in buffered soln, add aniline or to monomethylaniline, add again papoid, carry out enzymatic reaction, after completion of the reaction, filter, insolubles is that N-acetyl-L-methylselenocysteinefrom aniline or N-acetyl-L-methylselenocysteinefrom are to monomethylaniline, complete with hydrochloric acid or sulfuric acid heating hydrolysis, then with ammonia neutralization, obtain L-methylselenocysteinefrom; Filtrate is containing N-acetyl-D-methylselenocysteinefrom, complete with hydrochloric acid or sulfuric acid heating hydrolysis after concentrating under reduced pressure, then with ammonia neutralization, obtains D-methylselenocysteinefrom; Described enzymatic reaction is to carry out under 20-70 ℃ of condition in pH3-9, temperature.
CN201310502507.2A 2010-02-10 2010-02-10 Resolution method for Se-methylselenocysteine Pending CN103614449A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110628839A (en) * 2019-11-04 2019-12-31 济源市万洋华康生物科技有限公司 Method for green and efficient preparation of L-selenium methyl selenocysteine

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110628839A (en) * 2019-11-04 2019-12-31 济源市万洋华康生物科技有限公司 Method for green and efficient preparation of L-selenium methyl selenocysteine
CN110628839B (en) * 2019-11-04 2023-05-30 河南希百康健康产业有限公司 Method for preparing L-selenomethylselenocysteine

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Application publication date: 20140305