CN1295214C - Synthesis of seleno-methionine - Google Patents
Synthesis of seleno-methionine Download PDFInfo
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- CN1295214C CN1295214C CN 200510012329 CN200510012329A CN1295214C CN 1295214 C CN1295214 C CN 1295214C CN 200510012329 CN200510012329 CN 200510012329 CN 200510012329 A CN200510012329 A CN 200510012329A CN 1295214 C CN1295214 C CN 1295214C
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- aminobutyrolactone
- selenomethionine
- hydrochloride
- sodium
- methionine
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- 229960002718 selenomethionine Drugs 0.000 title claims abstract description 20
- RJFAYQIBOAGBLC-BYPYZUCNSA-N Selenium-L-methionine Chemical compound C[Se]CC[C@H](N)C(O)=O RJFAYQIBOAGBLC-BYPYZUCNSA-N 0.000 title claims abstract description 19
- RJFAYQIBOAGBLC-UHFFFAOYSA-N Selenomethionine Natural products C[Se]CCC(N)C(O)=O RJFAYQIBOAGBLC-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 230000015572 biosynthetic process Effects 0.000 title description 5
- 238000003786 synthesis reaction Methods 0.000 title description 5
- XBKCXPRYTLOQKS-UHFFFAOYSA-N (2-oxooxolan-3-yl)azanium;chloride Chemical compound Cl.NC1CCOC1=O XBKCXPRYTLOQKS-UHFFFAOYSA-N 0.000 claims abstract description 16
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims abstract description 8
- 229930182817 methionine Natural products 0.000 claims abstract description 8
- MJEJPPQFUJAISK-UHFFFAOYSA-M sodium methaneselenolate Chemical compound [Na+].[Se-]C MJEJPPQFUJAISK-UHFFFAOYSA-M 0.000 claims abstract description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 4
- 238000010189 synthetic method Methods 0.000 claims description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- QJPWUUJVYOJNMH-UHFFFAOYSA-N homoserine lactone Chemical class NC1CCOC1=O QJPWUUJVYOJNMH-UHFFFAOYSA-N 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- OOYOEHGKYKMRJI-UHFFFAOYSA-N methylseleninylmethane Chemical compound C[Se](C)=O OOYOEHGKYKMRJI-UHFFFAOYSA-N 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 229910052711 selenium Inorganic materials 0.000 abstract description 11
- 239000011669 selenium Substances 0.000 abstract description 11
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 abstract description 10
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- 238000001308 synthesis method Methods 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 3
- 238000007363 ring formation reaction Methods 0.000 abstract description 2
- 238000007142 ring opening reaction Methods 0.000 abstract description 2
- -1 selenium amino acid Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229940091258 selenium supplement Drugs 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- PMYDPQQPEAYXKD-UHFFFAOYSA-N 3-hydroxy-n-naphthalen-2-ylnaphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(NC(=O)C3=CC4=CC=CC=C4C=C3O)=CC=C21 PMYDPQQPEAYXKD-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- BVTBRVFYZUCAKH-UHFFFAOYSA-L disodium selenite Chemical compound [Na+].[Na+].[O-][Se]([O-])=O BVTBRVFYZUCAKH-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229960001881 sodium selenate Drugs 0.000 description 2
- 235000018716 sodium selenate Nutrition 0.000 description 2
- 239000011655 sodium selenate Substances 0.000 description 2
- 229960001471 sodium selenite Drugs 0.000 description 2
- 235000015921 sodium selenite Nutrition 0.000 description 2
- 239000011781 sodium selenite Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VXVKGIZYLHTHMR-WCCKRBBISA-N (2s)-2-amino-4-methylselanylbutanoic acid;selenium Chemical compound [Se].C[Se]CC[C@H](N)C(O)=O VXVKGIZYLHTHMR-WCCKRBBISA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000036737 immune function Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 150000002742 methionines Chemical class 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及一种含硒化合物的合成方法，具体属于有机硒类氨基酸药物——硒代蛋氨酸的合成方法，即(1)由蛋氨酸经环合得α-氨基丁内酯盐酸盐；(2)由甲硒醇钠和α-氨基丁内酯盐酸盐进行加成开环制得硒代蛋氨酸。本发明反应条件温和，步骤简单，易于操作，产品总收率48.1%，适合于工业化生产。The invention relates to a synthesis method of a selenium-containing compound, specifically belonging to a synthesis method of an organic selenium amino acid drug—selenomethionine, that is, (1) α-aminobutyrolactone hydrochloride is obtained by cyclization of methionine; (2) ) to prepare selenomethionine by addition ring-opening of sodium methylselenide and α-aminobutyrolactone hydrochloride. The invention has mild reaction conditions, simple steps, easy operation, and a total product yield of 48.1%, which is suitable for industrial production.
Description
技术领域technical field
本发明涉及一种含硒的化合物，具体属于一种硒代蛋氨酸的合成方法。The invention relates to a selenium-containing compound, in particular to a synthesis method of selenomethionine.
背景技术Background technique
硒是人体必须的微量元素之一，有多种免疫与生物学功能，尤其是它的预防心血管病，抗肿瘤，对抗病毒性疾病以及抗衰老等功能，另外，硒对人体的营养作用以及补硒对某些疾病的防止作用也非常重要，近年来引起人们的特别关注。目前市场上的补硒制品分为无机和有机硒两大类，无机硒以硒酸钠和亚硒酸钠为主，有机硒则以硒代蛋氨酸为主。无机硒(硒酸钠和亚硒酸钠)易于制备，但是副作用大，而且人体的吸收和利用率低，因此在发达国家已不提倡使用。有机硒(硒代蛋氨酸)属于蛋氨酸的衍生物，毒副作用均很低，而且易于吸收，是一种较为安全可靠的补硒佳品。但是长期以来，由于硒代蛋氨酸的合成工艺复杂和产率低等原因，目前在世界上尚无工业化生产，仅有的供应商——美国的Sigma-Aldrich公司只提供试剂级的产品，价格更是高的吓人——每100毫克82美元，也就是1克合人民币大约6000多元，所以目前硒代蛋氨酸的生物、生理、药理活性研究的很多，但尚没有直接将其作为补硒商品。国际上最新的关于硒代蛋氨酸合成工艺(T.Koch and O.Buchardt，Synthesis，1993，1065-1067)的研究即从蛋氨酸出发经过7步反应得到目标化合物，总收率不到30％；国内也有人对硒代蛋氨酸的合成工艺进行了研究(宋连卿、林钰等，郑州粮食学院学报，1999，20，62-64)，即从γ-丁内酯出发，经过溴化、氨代加成等5步，总收率约33％。总之，现有的合成工艺均存在工艺路线复杂，收率低，而且设备投资大，很难实现工业化生产。Selenium is one of the essential trace elements for the human body. It has a variety of immune and biological functions, especially its functions of preventing cardiovascular disease, anti-tumor, anti-viral diseases and anti-aging. In addition, the nutritional effect of selenium on the human body and Selenium supplementation is also very important in the prevention of certain diseases, which has attracted special attention in recent years. At present, selenium supplement products on the market are divided into two categories: inorganic selenium and organic selenium. Inorganic selenium is mainly composed of sodium selenate and sodium selenite, while organic selenium is mainly composed of selenomethionine. Inorganic selenium (sodium selenate and sodium selenite) is easy to prepare, but its side effects are large, and the absorption and utilization rate of the human body is low, so it is not recommended to be used in developed countries. Organic selenium (selenomethionine) is a derivative of methionine, with low toxicity and side effects, and easy to absorb. It is a relatively safe and reliable selenium supplement. But for a long time, due to reasons such as the complex synthesis process and low yield of selenomethionine, there is no industrialized production in the world at present, and the only supplier—Sigma-Aldrich company in the United States only provides reagent-grade products, and the price is lower. It is frighteningly high - 82 US dollars per 100 mg, which is about 6,000 yuan per gram, so there are many studies on the biological, physiological, and pharmacological activities of selenomethionine, but it has not been directly used as a selenium supplement product. The latest international research on the synthesis process of selenomethionine (T.Koch and O.Buchardt, Synthesis, 1993, 1065-1067) is to obtain the target compound from methionine through 7 steps of reaction, and the total yield is less than 30%. Some people have also studied the synthesis process of selenomethionine (Song Lianqing, Lin Yu, etc., Journal of Zhengzhou Grain Institute, 1999, 20, 62-64), that is, starting from γ-butyrolactone, after bromination and amino addition After 5 steps, the total yield is about 33%. In a word, the existing synthetic processes all have complex process routes, low yields, and large investment in equipment, making it difficult to realize industrialized production.
发明内容Contents of the invention
本发明的目的在于提供一种反应条件温和，步骤简单，产品收率较高，利于工业化生产的硒代蛋氨酸合成方法。The object of the present invention is to provide a kind of selenomethionine synthetic method that reaction condition is mild, and step is simple, and product yield is higher, and is beneficial to industrial production.
本发明所提供的硒代蛋氨酸的合成方法包括如下步骤：The synthetic method of selenomethionine provided by the present invention comprises the steps:
(1)α-氨基丁内酯盐酸盐的制备：(1) Preparation of α-aminobutyrolactone hydrochloride:
将蛋氨酸与碘甲烷反应，然后用NaHCO3水溶液水解，加盐酸酸化、酯化得α-氨基丁内酯盐酸盐。React methionine with methyl iodide, then hydrolyze with NaHCO 3 aqueous solution, acidify and esterify with hydrochloric acid to obtain α-aminobutyrolactone hydrochloride.
具体步骤为：将蛋氨酸加入到甲醇水溶液中(甲醇∶水＝1∶5-8)，在搅拌下加入相当于2-3倍蛋氨酸摩尔量的碘甲烷；搅拌反应30-60小时，蒸馏将反应液浓缩到体积约原来的1/2-1/4，加NaHCO3水溶液水解，加热回流10-20小时，冷却，蒸馏除去溶剂，加浓盐酸酸化，同时加入适量的30％ H2O2，搅拌反应1-2.5小时，用乙醚萃取除去碘，将水相继续回流1-2小时，冷却，蒸馏除去溶剂，残余固体用乙醇提取，提取液浓缩后加浓盐酸并加热回流1-2小时，蒸馏除去溶剂，粗产物用乙醇水溶液重结晶得白色产品α-氨基丁内酯盐酸盐，反应方程式如下所示：The specific steps are: add methionine to methanol aqueous solution (methanol: water = 1: 5-8), add methyl iodide equivalent to 2-3 times the molar amount of methionine under stirring; stir and react for 30-60 hours, and distill the reaction Concentrate the solution to about 1/2-1/4 of its original volume, add NaHCO 3 aqueous solution to hydrolyze, heat and reflux for 10-20 hours, cool, distill off the solvent, add concentrated hydrochloric acid to acidify, and add an appropriate amount of 30% H 2 O 2 at the same time, Stir the reaction for 1-2.5 hours, remove iodine by extraction with ether, continue to reflux the water phase for 1-2 hours, cool, distill off the solvent, extract the residual solid with ethanol, concentrate the extract, add concentrated hydrochloric acid and heat to reflux for 1-2 hours, The solvent is distilled off, and the crude product is recrystallized with ethanol aqueous solution to obtain the white product α-aminobutyrolactone hydrochloride, and the reaction equation is as follows:
(2)硒代蛋氨酸的制备：(2) Preparation of selenomethionine:
在氮气保护和搅拌下，按摩尔比α-氨基丁内酯盐酸盐∶甲硒醇钠＝1∶1-2.5，将制备的α-氨基丁内酯盐酸盐加入到甲硒醇钠的无水乙醇溶液中，加热回流6-10小时，冷却，加乙酸中和至pH值为5.75，过滤得白色产品硒代蛋氨酸，反应方程式如下所示：Under nitrogen protection and stirring, according to the molar ratio of α-aminobutyrolactone hydrochloride: sodium methylselenide=1: 1-2.5, the prepared α-aminobutyrolactone hydrochloride is added to the sodium methylselenide In absolute ethanol solution, heat and reflux for 6-10 hours, cool, add acetic acid to neutralize to a pH value of 5.75, and filter to obtain the white product selenomethionine. The reaction equation is as follows:
优选步骤(2)中的按摩尔比α-氨基丁内酯盐酸盐∶甲硒醇钠＝1∶2-2.3。Preferably, the molar ratio of α-aminobutyrolactone hydrochloride: sodium methylselenide in step (2) is 1: 2-2.3.
本发明提供的合成方法反应条件温和，步骤简单，蛋氨酸经环合和加成开环两个主要步骤完成，产品收率较高(最高收率48.1％)，适于工业化生产。The synthesis method provided by the invention has mild reaction conditions and simple steps. The methionine is completed through two main steps of cyclization and addition ring opening, and the product yield is high (the highest yield is 48.1%), which is suitable for industrial production.
具体实施方式Detailed ways
实施例1Example 1
步骤(1)、α-氨基丁内酯盐酸盐的制备The preparation of step (1), α-aminobutyrolactone hydrochloride
将75g(0.50mol)蛋氨酸加入到甲醇水溶液中(甲醇/水＝200∶1400)，在搅拌下加入相当于75mL(1.21mol)的碘甲烷。搅拌反应48小时，蒸馏将反应液浓缩到体积约原来的1/3，加500mL水，42g(0.5mol)NaHCO3水溶液水解，加热回流15小时，冷却，蒸馏除去溶剂，加1000mL浓盐酸酸化，同时加入25mL30％的H2O2，搅拌反应1小时，用乙醚萃取除去碘，将水相继续回流1小时，冷却，蒸馏除去溶剂，残余固体用乙醇多次提取，提取液浓缩后加1000mL浓盐酸并加热回流1小时，蒸馏除去溶剂，粗产物用乙醇/水重结晶的白色产品α-氨基丁内酯盐酸盐50.6g，产率65％。75g (0.50mol) of methionine was added to methanol aqueous solution (methanol/water=200:1400), and 75mL (1.21mol) of methyl iodide was added under stirring. Stir the reaction for 48 hours, distill and concentrate the reaction solution to about 1/3 of its original volume, add 500mL of water, hydrolyze with 42g (0.5mol) NaHCO 3 aqueous solution, heat and reflux for 15 hours, cool, distill off the solvent, add 1000mL of concentrated hydrochloric acid to acidify, At the same time, 25 mL of 30% H 2 O 2 was added, stirred for 1 hour, extracted with ether to remove iodine, continued to reflux the water phase for 1 hour, cooled, distilled off the solvent, extracted the residual solid with ethanol several times, concentrated the extract and added 1000 mL concentrated hydrochloric acid and heated to reflux for 1 hour, the solvent was distilled off, and the crude product was recrystallized with ethanol/water to obtain 50.6 g of α-aminobutyrolactone hydrochloride, a yield of 65%.
步骤(2)、硒代蛋氨酸的制备The preparation of step (2), selenomethionine
在氮气保护和搅拌下，将上述制备的α-氨基丁内酯盐酸盐7.74g(0.056mol)加入到甲硒醇钠17.38g(0.118mol)的无水乙醇溶液中，加热回流8小时，冷却，加乙酸中和至pH值为5.75，过滤得白色产品硒代蛋氨酸，8.25g，产率74％。Under nitrogen protection and stirring, the α-aminobutyrolactone hydrochloride 7.74g (0.056mol) prepared above was added in the absolute ethanol solution of sodium methylselenide 17.38g (0.118mol), heated to reflux for 8 hours, Cool, add acetic acid to neutralize until the pH value is 5.75, and filter to obtain a white product, selenomethionine, 8.25 g, with a yield of 74%.
实施例2Example 2
步骤(1)、同实施例1。Step (1), with embodiment 1.
步骤(2)、在氮气保护和搅拌下，将上述制备的α-氨基丁内酯盐酸盐7.74g(0.056mol)加入到甲硒醇钠12.41g(0.084mol)的无水乙醇溶液中，加热回流8小时，冷却，加乙酸中和至pH值为5.75，过滤得白色产品硒代蛋氨酸，5.85g，产率53％。Step (2), under nitrogen protection and stirring, the α-aminobutyrolactone hydrochloride 7.74g (0.056mol) prepared above was added in the absolute ethanol solution of sodium methylselenide 12.41g (0.084mol), Heat to reflux for 8 hours, cool, add acetic acid to neutralize until the pH value is 5.75, and filter to obtain a white product, selenomethionine, 5.85 g, with a yield of 53%.
实施例3Example 3
步骤(1)、同实施例1。Step (1), with embodiment 1.
步骤(2)、在氮气保护和搅拌下，将上述制备的α-氨基丁内酯盐酸盐7.74g(0.056mol)加入到甲硒醇钠20.68g(0.141mol)的无水乙醇溶液中，加热回流8小时，冷却，加乙酸中和至pH值为5.75，过滤得白色产品硒代蛋氨酸，8.29g，产率74％。Step (2), under nitrogen protection and stirring, the α-aminobutyrolactone hydrochloride 7.74g (0.056mol) prepared above was added in the absolute ethanol solution of sodium methylselenide 20.68g (0.141mol), Heating to reflux for 8 hours, cooling, adding acetic acid to neutralize to a pH value of 5.75, and filtering to obtain a white product, selenomethionine, 8.29 g, with a yield of 74%.
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| BR112012022506A2 (en) * | 2010-03-09 | 2017-09-19 | Novus Int Inc | preparation of methionine or selenomethionine from homoserin via a lactone intermediate. |
| FR2965561B1 (en) * | 2010-10-05 | 2012-08-31 | Adisseo France Sas | PROCESS FOR PREPARING AN AMINO ACID FROM 2-AMINOBUTYROLACTONE |
| CN102321004A (en) * | 2011-06-04 | 2012-01-18 | 山西大学 | The compound method of a kind of L-(+)-selenomethionine |
| CN102558005A (en) * | 2012-01-11 | 2012-07-11 | 张家港阿拉宁生化技术有限公司 | Environmentally-friendly method for synthesizing selenomethionine |
| CN106220539B (en) * | 2016-07-25 | 2018-04-03 | 四川新一美生物科技有限公司 | A kind of preparation method of selenomethionine |
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