Kinetic resolution of racemic alcohols catalyzed by minimal artificial acylases derived from L-histidine
Kinetic resolution of racemic alcohols catalyzed by minimal artificial acylases derived from L-histidine
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DOI：
10.1016/j.tet.2007.02.020
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发表时间：
2007-07-02
期刊：
影响因子：
2.1
通讯作者：
Ishihara, Kazuaki
中科院分区：
文献类型：
--
作者：
Kosugi, Yuji;Akakura, Matsujiro;Ishihara, Kazuaki
N(pi)-methyl-N(alpha)-(2，4，6-triisopropyl-benzenesulfonyl)-L-组氨酸的叔丁基二苯基硅基醚和三(三甲基硅基)硅基醚人工酰基酶是简单的小分子，只含有一个来自天然L组氨酸的手性碳中心。这些人工酰基酶催化外消旋仲醇与异丁酸酐的不对称酰化反应，得到旋光活性异丁酸酯和旋光活性醇，其S(k(快反应对映体)/k(慢反应对映体))值高达132。催化剂的磺胺基团与底物之间的氢键作用对于通过催化不对称酰化反应获得高水平的动力学拆分是必不可少的。此外，还开发了一种可重复使用的聚苯乙烯结合的人工酰基酶，以检验其实用性。(C)2007爱思唯尔有限公司。保留所有权利。
The artificial acylases, tert-butyldiphenylsilyl ether and tris(trimethylsilyl) silyl ether of N(pi)-methyl-N(alpha)-(2,4,6-triisopropyl-benzenesulfonyl)-L- histidinol, are simple and small molecules, which contain only one chiral carbon center that originates from natural L-histidine. Asymmetric acylation of racemic secondary alcohols with isobutyric anhydride induced by these artificial acylases gave optically active isobutyrates and optically active alcohols with an S(k(fast-reacting enantiomer)/k(slow-reacting enantiomer)) value of up to 132. One hydrogen bonding interaction between a sulfonamidyl group of the catalysts and a substrate should be essential for inducing the high level of kinetic resolution through catalytic asymmetric acylation. Furthermore, a reusable polystyrene-bound artificial acylase was developed to examine its practicality. (c) 2007 Elsevier Ltd. All rights reserved.