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*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

9 Citations (Scopus)
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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.

Original languageEnglish
Pages (from-to)11120-11126
Number of pages7
JournalAngewandte Chemie - International Edition
Issue number20
Publication statusPublished - 10-May-2021


  • amino acid
  • chiral amplification
  • origin of life
  • phosphoramidate
  • phosphorylation

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