One-pot, two-step cascade synthesis of naturally rare L-erythro (3S,4S) ketoses by coupling a thermostable transaminase and transketolase
One-pot, two-step cascade synthesis of naturally rare L-erythro (3S,4S) ketoses by coupling a thermostable transaminase and transketolase
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DOI：
10.1039/c6gc02015a
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发表时间：
2017-01-21
期刊：
影响因子：
9.8
通讯作者：
Hecquet, Laurence
中科院分区：
文献类型：
--
作者：
Lorilliere, Marion;De Sousa, Maxime;Hecquet, Laurence
在高温下进行由热稳定性转氨酶和转酮醇酶催化的两个酶促步骤的有效同时级联，从而允许合成天然稀有的L-β-（3S，4S）酮糖。L-核酮糖、5-脱氧-L-核酮糖、D-塔格糖和L-阿洛酮糖是一类具有重要生物活性的手性结构单元，具有良好的立体选择性和较高的收率。一种来自嗜热脂肪土芽孢杆菌的热稳定转酮醇酶，其在高温下催化由（2S）-羟基化醛和β-羟基丙酮酸立体特异性合成L-邻位（3S，4S）-构型的酮糖，其中后者是使用来自嗜热细菌嗜热菌嗜一氧化碳热菌的新型热稳定L-α-转氨酶以前所未有的方式由天然L-丝氨酸和丙酮酸原位产生的。总的来说，这种级联合成防止了不稳定的β-羟基丙酮酸酯的热分解，并提供了一种有效和环境友好的方法。
An efficient simultaneous cascade of two enzymatic steps catalyzed by a thermostable transaminase and transketolase was performed at elevated temperatures allowing the synthesis of naturally rare L-erythro (3S,4S) ketoses. L-ribulose, 5-deoxy-L-ribulose, D-tagatose and L-psicose, which are highly valuable chiral building blocks and display prominent biological properties, were obtained on a preparative scale with excellent stereoselectivities and good yields. A thermostable transketolase from Geobacillus stearothermophilus catalyzed at high temperatures the stereospecific synthesis of L-erythro (3S,4S)-configured ketoses from (2S)-hydroxylated aldehydes and beta-hydroxypyruvate in which the latter is generated in an unprecedented manner in situ from natural L-serine and pyruvate using a novel thermostable L-a-transaminase from the thermophilic bacterium Thermosinus carboxydivorans. Overall, this cascade synthesis prevents the thermal decomposition of the labile beta-hydroxypyruvate and offers an efficient and environmentally friendly procedure.