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The self-disproportionation of enantiomers (SDE) of α-amino acid derivatives: facets of steric and electronic properties.
- Source :
-
Amino Acids . Feb2019, Vol. 51 Issue 2, p283-294. 12p. - Publication Year :
- 2019
-
Abstract
- α-Amino acids (α-AAs) are in extremely high demand in nearly every sector of the food and health-related chemical industries and continue to be the subject of intense multidisciplinary research. The self-disproportionation of enantiomers (SDE) is an emerging and one of the least studied areas of α-AA or enantiomeric properties, critically important for their production and application. In the present work, we report a detailed study of the SDE via achiral, gravity-driven column chromatography for a set of N-acylated, N-carbonylated, N-fluoroacylated, and N-thioacylated α-amino acid esters. As well as thioacylation, attention was paid to the effect of altering the R group of the ester functionality, the side chain, or that of the acyl group attached to the amide nitrogen, whereby it was found that electron-withdrawing groups in the latter moiety had a pronounced effect on the magnitude and behavior of the resulting SDE phenomenon. Intriguingly, in the case of N-fluoroacylated derivatives, by favoring the formation of dimeric associates and effecting a strong bias toward homochiral associates over heterochiral associates, the SDE magnitude was greatly reduced contrary to intuitive expectations. Energy estimates resulted from DFT calculations. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 09394451
- Volume :
- 51
- Issue :
- 2
- Database :
- Academic Search Index
- Journal :
- Amino Acids
- Publication Type :
- Academic Journal
- Accession number :
- 134892073
- Full Text :
- https://doi.org/10.1007/s00726-018-2664-x