Chiral Amplification of Phosphoramidates of Amines and Amino Acids in Water

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

    Research output: Contribution to journalArticleAcademicpeer-review

    Abstract

    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
    Volume60
    Issue number20
    DOIs
    Publication statusPublished - 10 May 2021

    Bibliographical note

    Funding Information:
    This work was supported financially by the Netherlands Organization for Scientific Research (NWO‐CW), and the Ministry of Education, Culture and Science (Gravitation Program no. 024.001.035). The X‐ray diffractometer at Utrecht University has been financed by the Netherlands Organization for Scientific Research (NWO).

    Funding Information:
    This work was supported financially by the Netherlands Organization for Scientific Research (NWO-CW), and the Ministry of Education, Culture and Science (Gravitation Program no. 024.001.035). The X-ray diffractometer at Utrecht University has been financed by the Netherlands Organization for Scientific Research (NWO).

    Publisher Copyright:
    © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH

    Keywords

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

    Fingerprint

    Dive into the research topics of 'Chiral Amplification of Phosphoramidates of Amines and Amino Acids in Water'. Together they form a unique fingerprint.

    Cite this