Chiral Amplification of Phosphoramidates of Amines and Amino Acids in Water. Issue 20 (6th April 2021)

• Record Type: Journal Article
• Authors: Dašková, Vanda; Buter, Jeffrey; Schoonen, Anne K.; Lutz, Martin; de Vries, Folkert; Feringa, Ben L.
• Is Part Of: Angewandte Chemie international edition. Volume 60:Issue 20(2021)
• Page Start: 11120
• Page End: 11126
• Publication Date: 2021-04-06
• Subjects: amino acid -- chiral amplification -- origin of life -- phosphoramidate -- phosphorylation; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202014955
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : The origin of homochirality is a fundamental scientific question. We show that dissolution behavior of racemic and enantiopure amines can be altered by conversion into phosphoramidates. Stirring a solid scalemic mixture in water leads to enantioenrichment of the solution phase (>90 % ee ). Amplification of amino acids and their derivatives show that phosphorylation can serve as a potentially viable source of prebiotic homochirality.