Chiral Amplification of Phosphoramidates of Amines and Amino Acids in Water

Vanda Dašková, Jeffrey Buter, Anne K. Schoonen, Martin Lutz, Folkert de Vries, Ben L. Feringa*

*Bijbehorende auteur voor dit werk

OnderzoeksoutputAcademicpeer review

9 Citaten (Scopus)
62 Downloads (Pure)


The origin of biomolecular homochirality continues to be one of the most fascinating aspects of prebiotic chemistry. Various amplification strategies for chiral compounds to enhance a small chiral preference have been reported, but none of these involves phosphorylation, one of nature's essential chemical reactions. Here we present a simple and robust concept of phosphorylation-based chiral amplification of amines and amino acids in water. By exploiting the difference in solubility of a racemic phosphoramidate and its enantiopure form, we achieved enantioenrichment in solution. Starting with near racemic, phenylethylamine-based phosphoramidates, ee's of up to 95 % are reached in a single amplification step. Particularly noteworthy is the enantioenrichment of phosphorylated amino acids and their derivatives, which might point to a potential role of phosphorus en-route to prebiotic homochirality.

Originele taal-2English
Pagina's (van-tot)11120-11126
Aantal pagina's7
TijdschriftAngewandte Chemie - International Edition
Nummer van het tijdschrift20
StatusPublished - 10-mei-2021


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