A real amplification of an initial enantiomeric excess can be detected when two amino acids are sublimed at high temperature, even if one of the components is a racemic compound that does not convert into a conglomerate by sublimation.
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The self-disproportionation of enantiomers (SDE) of amino acids and their derivatives.
Amino Acids
June 2019
Molecular Structure Analysis, German Cancer Research Center (DKFZ), Im Neuenheimer Feld 280, 69120, Heidelberg, Germany.
This review covers the phenomenon of the self-disproportionation of enantiomers (SDE) of amino acids and their derivatives in all its guises from phase transformations (recrystallization, sublimation, and distillation), to the application of force fields, through to chromatography including HPLC, MPLC, gravity-driven column chromatography, and SEC. The relevance of the SDE phenomenon to amino acid research and to marketed pharmaceuticals is clear given the potential for alteration of the enantiomeric excess of a portion of a scalemic sample. In addition, the possible contribution of the SDE phenomenon to the genesis of prebiotic homochirality is considered.
View Article and Find Full Text PDFThe self-disproportionation of enantiomers (SDE): The effect of scaling down, potential problems versus prospective applications, possible new occurrences, and unrealized opportunities?
Electrophoresis
August 2019
Molecular Structure Analysis, German Cancer Research Center (DKFZ), Heidelberg, Germany.
This commentary discusses an important, though not widely appreciated, chiral phenomenon of molecular chirality that effectively always occurs whenever nonracemic samples are subjected to practically any physicochemical process (e.g., force field, recrystallization, sublimation, even distillation, etc.
View Article and Find Full Text PDFThe self-disproportionation of enantiomers (SDE): a menace or an opportunity?
Chem Sci
February 2018
Department of Organic Chemistry I , Faculty of Chemistry , University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3 , 20018 San Sebastián , Spain . Email:
Herein we report on the well-documented, yet not widely known, phenomenon of the self-disproportionation of enantiomers (SDE): the spontaneous fractionation of scalemic material into enantioenriched and -depleted fractions when any physicochemical process is applied. The SDE has implications ranging from the origins of prebiotic homochirality to unconventional enantiopurification methods, though the risks of altering the enantiomeric excess (ee) unintentionally, regrettably, remain greatly unappreciated. While recrystallization is well known as an SDE process, occurrences of the SDE in other processes are much less recognized, sublimation and even distillation.
View Article and Find Full Text PDFTransfer of Asymmetry between Proteinogenic Amino Acids under Harsh Conditions.
Orig Life Evol Biosph
September 2017
Institut des Sciences Chimiques de Rennes, École Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, 11 allée de Beaulieu, CS 50837, 35708, Rennes Cedex 7, France.
The heating above 400 °C of serine, cysteine, selenocysteine and threonine leads to a complete decomposition of the amino acids and to the formation in low yields of alanine for the three formers and of 2-aminobutyric acid for the latter. At higher temperature, this amino acid is observed only when sublimable α-alkyl-α-amino acids are present, and with an enantiomeric excess dependent on several parameters. Enantiopure or enantioenriched Ser, Cys, Sel or Thr is not able to transmit its enantiomeric excess to the amino acid formed during its decomposition.
View Article and Find Full Text PDFHigh temperature sublimation of α-amino acids: a realistic prebiotic process leading to large enantiomeric excess.
Chem Commun (Camb)
April 2015
Institut des Sciences Chimiques de Rennes, Ecole Nationale Supérieure de Chimie de Rennes, CNRS UMR 6226, 11 Allée de Beaulieu, CS50837, 35708 Rennes Cedex 7, France.
The reiterative high temperature co-sublimation of an enantiopure or an enantioenriched α-amino acid mixed with racemic α-amino acids leads to deracemization of the latter. A synergistic effect is observed for complex mixtures, and the sense of the handedness is, for all compounds, identical to that of the enantioenriched starting material.
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