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

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...

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Autores principales: Maeno, Mayaka, Tokunaga, Etsuko, Yamamoto, Takeshi, Suzuki, Toshiya, Ogino, Yoshiyuki, Ito, Emi, Shiro, Motoo, Asahi, Toru, Shibata, Norio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5811091/
https://www.ncbi.nlm.nih.gov/pubmed/29560192
http://dx.doi.org/10.1039/c4sc03047h
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author Maeno, Mayaka
Tokunaga, Etsuko
Yamamoto, Takeshi
Suzuki, Toshiya
Ogino, Yoshiyuki
Ito, Emi
Shiro, Motoo
Asahi, Toru
Shibata, Norio
author_facet Maeno, Mayaka
Tokunaga, Etsuko
Yamamoto, Takeshi
Suzuki, Toshiya
Ogino, Yoshiyuki
Ito, Emi
Shiro, Motoo
Asahi, Toru
Shibata, Norio
author_sort Maeno, Mayaka
collection PubMed
description 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.
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spelling pubmed-58110912018-03-20 Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications Maeno, Mayaka Tokunaga, Etsuko Yamamoto, Takeshi Suzuki, Toshiya Ogino, Yoshiyuki Ito, Emi Shiro, Motoo Asahi, Toru Shibata, Norio Chem Sci Chemistry 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. Royal Society of Chemistry 2015-02-01 2014-10-30 /pmc/articles/PMC5811091/ /pubmed/29560192 http://dx.doi.org/10.1039/c4sc03047h Text en This journal is © The Royal Society of Chemistry 2014 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Maeno, Mayaka
Tokunaga, Etsuko
Yamamoto, Takeshi
Suzuki, Toshiya
Ogino, Yoshiyuki
Ito, Emi
Shiro, Motoo
Asahi, Toru
Shibata, Norio
Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications
title Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications
title_full Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications
title_fullStr Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications
title_full_unstemmed Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications
title_short Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications
title_sort self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5811091/
https://www.ncbi.nlm.nih.gov/pubmed/29560192
http://dx.doi.org/10.1039/c4sc03047h
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