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制备对映体纯苯丙氨酸的廉价化学方法。

Inexpensive chemical method for preparation of enantiomerically pure phenylalanine.

作者信息

Moriwaki Hiroki, Resch Daniel, Li Hengguang, Ojima Iwao, Takeda Ryosuke, Aceña José Luis, Soloshonok Vadim

机构信息

Department of Chemistry, Institute of Chemical Biology and Drug Discovery, State University of New York at Stony Brook, Stony Brook, NY, 11794-3400, USA.

出版信息

Amino Acids. 2014 Apr;46(4):945-52. doi: 10.1007/s00726-013-1656-0. Epub 2014 Jan 3.

Abstract

Here, we report the most inexpensive procedure for chemical synthesis of enantiomerically pure phenylalanine. As a source of chirality, we use the ultimately inexpensive chiral auxiliary, 1-(phenyl)ethylamine, incorporated into the specially designed ligands which form the corresponding intermediate Ni(II) complexes with racemic phenylalanine. Diastereomerically pure Ni(II) complexes, containing either (S)- or (R)-phenylalanine, were disassembled to produce enantiomerically pure target amino acid, along with recycling the chiral ligand. All reactions were conducted under operationally convenient conditions, featuring high yields and thus underscoring attractive cost structure of this method.

摘要

在此,我们报道了对映体纯苯丙氨酸化学合成中成本最低的方法。作为手性源,我们使用了成本极低的手性助剂1-(苯基)乙胺,它被引入到经过特殊设计的配体中,这些配体与外消旋苯丙氨酸形成相应的中间体镍(II)配合物。含有(S)-或(R)-苯丙氨酸的非对映体纯镍(II)配合物被拆解,以生成对映体纯的目标氨基酸,同时实现手性配体的循环利用。所有反应均在操作简便的条件下进行,产率高,从而突出了该方法极具吸引力的成本结构。

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