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Amino Acids. 2016 Feb;48(2):605-13. doi: 10.1007/s00726-015-2152-5. Epub 2015 Dec 24.

Remarkable magnitude of the self-disproportionation of enantiomers (SDE) via achiral chromatography: application to the practical-scale enantiopurification of β-amino acid esters.

Author information

1
Institute of Chemistry, Jan Kochanowski University in Kielce, Świętokrzyska 15G, 25-406, Kielce, Poland. alicja.wzorek@ujk.edu.pl.
2
Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018, San Sebastián, Spain. alicja.wzorek@ujk.edu.pl.
3
Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018, San Sebastián, Spain.
4
Department of Chemistry, Tokyo Women's Medical University, 8-1 Kawada-cho, Shinjuku-ku, Tokyo, 162-8666, Japan.
5
Department of Heteroorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363, Łódź, Poland.
6
Institute of Chemistry, Environmental Protection and Biotechnology, Jan Dlugosz University in Czestochowa, Armii Krajowej 13/15, 42-201, Częstochowa, Poland.
7
Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018, San Sebastián, Spain. vadym.soloshonok@ehu.eus.
8
IKERBASQUE, Basque Foundation for Science, Alameda Urquijo 36-5, Plaza Bizkaia, 48011, Bilbao, Spain. vadym.soloshonok@ehu.eus.
9
Molecular Structure Analysis, German Cancer Research Center (DKFZ), Im Neuenheimer Feld 280, 69009, Heidelberg, Germany. k.klika@dkfz.de.

Abstract

We report the best performance yet for the self-disproportionation of enantiomers (SDE) via achiral chromatography as typically used in laboratories for the isolated yield of the excess enantiomer using N-acetyl β-amino acid ethyl esters. The results are the most convincing ever demonstration of the capability of the SDE for practical-scale enantiopurification as comparable, or even superior for some systems, to that of recrystallization. For example, from a sample of 94.4 % ee, a yield of 71 % of enantiopure material was isolated in a single chromatographic run. Moreover, the lack of an esoteric structural entity, e.g. strongly polarizing groups, such as, for instance CF3, highlights the fact that the phenomenon is not dependent on the presence of such and thus the process is relevant to any usual-type structure. In contrast to recrystallization, the procedure is predictable, general, and dependable, boding well for its widespread application in routine laboratory settings.

KEYWORDS:

Column chromatography; Enantiomeric enrichment; Recrystallization; Self-disproportionation of enantiomers (SDE)

PMID:
26704565
DOI:
10.1007/s00726-015-2152-5
[Indexed for MEDLINE]

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