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沙利度胺及其氟化类似物对映体的自歧化作用:重力驱动的非手性色谱法——作用机理及意义

Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue gravity-driven achiral chromatography: mechanistic rationale and implications.

作者信息

Maeno Mayaka, Tokunaga Etsuko, Yamamoto Takeshi, Suzuki Toshiya, Ogino Yoshiyuki, Ito Emi, Shiro Motoo, Asahi Toru, Shibata Norio

机构信息

Department of Nanopharmaceutical Sciences and Department of Frontier Materials , Nagoya Institute of Technology , Gokiso, Showa-ku , Nagoya 466-8555 , Japan . Email:

Department of Life Science and Medical Bioscience , Waseda University (TWIns) , Wakamatsu-cho 2-2, Shinjuku-ku , Tokyo 162-8480 , Japan . Email:

出版信息

Chem Sci. 2015 Feb 1;6(2):1043-1048. doi: 10.1039/c4sc03047h. Epub 2014 Oct 30.

Abstract

We report on the self-disproportionation of enantiomers (SDE) of non-racemic thalidomide () and 3'-fluorothalidomide () under the conditions of gravity-driven achiral silica-gel chromatography. The presence of a fluorine atom on the chiral center dramatically alters the structure and polarity of and , resulting in the opposite SDE profile on silica-gel.

摘要

我们报道了在重力驱动的非手性硅胶色谱条件下,非外消旋沙利度胺()和3'-氟沙利度胺()对映体的自歧化作用(SDE)。手性中心上氟原子的存在显著改变了和的结构与极性,导致在硅胶上出现相反的SDE图谱。

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