title: Transfer of Asymmetry between Proteinogenic Amino Acids under Harsh Conditions.
abstract: 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. The presence during the sublimation-decomposition of enantioenriched valine or isoleucine leads to the enantioenrichment of all sublimable amino acids independently of the presence of many decomposition products coming from the unstable derivative. All these studies give information on a potentially prebiotic key-reaction of abiotic transformations between α-amino acids and their evolution to homochirality.
authors.affiliation: Boreskov Institute of Catalysis of the Siberian Branch of the Russian Academy of Sciences, pr. Lavrentieva, 5, 630090, Novosibirsk, Russia.|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.
authors.forename: Arkadii V
authors.initials: AV
authors.lastname: Tarasevych
authors.affiliation: 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.
authors.forename: Thomas
authors.initials: T
authors.lastname: Vives
authors.affiliation: Boreskov Institute of Catalysis of the Siberian Branch of the Russian Academy of Sciences, pr. Lavrentieva, 5, 630090, Novosibirsk, Russia.|Novosibirsk State University, Pirogova str. 2, 630090, Novosibirsk, Russia.
authors.forename: Valeriy N
authors.initials: VN
authors.lastname: Snytnikov
authors.affiliation: 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. jean-claude.guillemin@ensc-rennes.fr.
authors.forename: Jean-Claude
authors.initials: JC
authors.lastname: Guillemin
mesh_terms: D000409:Alanine / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D000613:Aminobutyrates / Q000737:chemistry*; D019418:Evolution, Chemical; D006358:Hot Temperature; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D000613:Aminobutyrates; C012223:alpha-aminobutyric acid; D000409:Alanine
keywords: Amino acid; Enantioenrichment; Sublimation; Transfer of asymmetry