L-硒代蛋氨酸的合成及工艺优化
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暨南大学理工学院

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Synthesis and process optimization of L-Selenomethionine
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1.Jinan University;2.College of Science and Engineering, Jinan University;3.College of Science and Engineering,Jinan University;4.College of Science and Engineering。Jinan University;5.College of Science and Engineering, Jinan University

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    摘要:

    将蛋氨酸(I)烷基化后再经过溴取代反应生成溴代高丝氨酸溴酸盐(III);接着将硒分别和三种还原剂反应得到二硒化二钠后与化合物III反应;得到的硒代高胱氨酸(IV)经由三乙酰氧基硼氢化钠还原、碘甲烷甲基化获得硒代蛋氨酸(V)。对其主要步骤进行优化筛选,获得最优的合成工艺条件:采用新型还原剂三乙酰氧基硼氢化钠制备二硒化二钠可以获得的中间产物IV收率较高,而且当氢氧化钠与三乙酰氧基硼氢化钠摩尔比为4.0:1.0时,化合物III的最高产率为62.42%;采用化合物IV、碘甲烷摩尔比1.0:2.0,以及氢氧化钠与三乙酰氧基硼氢化钠的摩尔比2.7:1.0,可获得终产物V的最高产率为75.79%;最终产物V的结构结晶纯化(纯度95%)后结合质谱、氢谱、碳谱进行确证。

    Abstract:

    Firstly, Methionine (I) is alkylated and then brominated to form bromohomoserine bromate (III). Secondly, Selenium reacts with three reducing agents to obtain disodium diselenide, and then reacts with compound III to obtain selenocysteine (IV); Finally, Selenomethionine (V) was formed by reduction of sodium triacetoxyborohydride and methyl iodide. The main steps were optimized and the optimal synthesis conditions were obtained: the preparation of disodium diselenide with a new reductant sodium triacetoxyborohydride could obtain a higher yield of intermediate product IV, and the highest yield of compound III was 62.42% when the molar ratio of sodium hydroxide to sodium triacetoxyborohydride was 4.0:1.0. When the molar ratio of compound IV to iodomethane was 1.0:2.0 and the molar ratio of sodium hydroxide to sodium triacetoxyborohydride was 2.7:1.0, the highest yield of final product V was 75.79%; The structure of the final product V was confirmed by mass spectrometry, hydrogen spectrum and carbon spectrum after crystallization and purification (purity 95%).

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戴扬晓,廖津,杨佩玲,李艺菲,欧仕益,周华. L-硒代蛋氨酸的合成及工艺优化[J].精细化工,2022,39(8):

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  • 收稿日期:2022-01-11
  • 最后修改日期:2022-03-06
  • 录用日期:2022-03-09
  • 在线发布日期: 2022-07-05
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