ArticleAngewandte Chemie (International ed. in English)2021
Chiral Amplification of Phosphoramidates of Amines and Amino Acids in Water.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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4 citing papers in PubMed.
- Toward Chiral Recognition by Design: Uncovering the Self-Enantioresolving Properties of Chiral Amine Derivatives.Journal of the American Chemical Society · 2025Article
- Ultrasensitive quantification of trace amines based onJournal of pharmaceutical analysis · 2023Article
- Turning Enantiomeric Relationships into Diastereomeric Ones: Self-Resolving α-Ureidophosphonates and Their Organocatalytic Enantioselective Synthesis.Journal of the American Chemical Society · 2022Article
- Chiral Amplification of Phosphoramidates of Amines and Amino Acids in Water.Angewandte Chemie (International ed. in English) · 2021Article
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6 authors.
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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.
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