Issue 2, 2015
From the journal:

Chemical Science

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

Mayaka Maeno,a   Etsuko Tokunaga,a   Takeshi Yamamoto,a   Toshiya Suzuki,b   Yoshiyuki Ogino,b   Emi Ito,a   Motoo Shiro,c   Toru Asahi*b  and  Norio Shibata*a  

* Corresponding authors

a Department of Nanopharmaceutical Sciences and Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan
E-mail: nozshiba@nitech.ac.jp
Fax: +81-52-735-7543

b Department of Life Science and Medical Bioscience, Waseda University (TWIns), Wakamatsu-cho 2-2, Shinjuku-ku, Tokyo 162-8480, Japan
E-mail: tasahi@waseda.jp

c Consolidated Research Institute for Advanced Science and Medical Care, Waseda University (ASMeW), Waseda-tsurumaki-cho 513, Shinjuku-ku, Tokyo 162-0041, Japan

Abstract

We report on the self-disproportionation of enantiomers (SDE) of non-racemic thalidomide (1) and 3′-fluorothalidomide (2) 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 1 and 2, resulting in the opposite SDE profile on silica-gel.

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

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Article information

DOI
https://doi.org/10.1039/C4SC03047H
Article type
Edge Article
Submitted
03 Oct 2014
Accepted
30 Oct 2014
First published
30 Oct 2014
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2015,6, 1043-1048

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

M. Maeno, E. Tokunaga, T. Yamamoto, T. Suzuki, Y. Ogino, E. Ito, M. Shiro, T. Asahi and N. Shibata, Chem. Sci., 2015, 6, 1043 DOI: 10.1039/C4SC03047H

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