Abstract
This article is concerned with the chiral amplification of oligopeptides formed in the polymerization of chiral, nonracemic mixtures of the N-carboxyanhydride (NCA) of Leu and Glu in aqueous solution. Labeling (deuteration) of one enantiomer and reversed-phase and normal-phase high-performance liquid chromatography mass spectrometry (RP- and NP-HPLC/MS, respectively) were used to determine the product distribution, both with respect to oligopeptide chain length and stereoisomer distribution. Starting the polymerization with an enantiomeric excess (ee) of 20% of the L-enantiomer (L-amino acid/D-amino acid 6 : 4) leads to an ee of 73% at the level of the homochiral enantiomeric (Leu)5, and of 71% at the level of the homochiral enantiomeric (Glu)7. For the Leu system and in the presence of a solid support (quartz), the ee reached values of up to 100%. We argue that such amplification processes could be relevant for the chemical evolution towards single-handedness.
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