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Chiral Amplification of Phosphoramidates of Amines and Amino Acids in Water
Author(s) -
Dašková Vanda,
Buter Jeffrey,
Schoonen Anne K.,
Lutz Martin,
Vries Folkert,
Feringa Ben L.
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202014955
Subject(s) - homochirality , enantiopure drug , chemistry , phosphoramidate , amino acid , chirality (physics) , organic chemistry , combinatorial chemistry , stereochemistry , enantioselective synthesis , catalysis , biochemistry , chiral symmetry , nambu–jona lasinio model , physics , quantum mechanics , quark
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.