Highly Enantioselective Extraction of Phenylglycine by a Chiral Macrocyclic Receptor Based on Supramolecular Interactions

María G Turiel; José J Garrido-González; Luis Simón; Francisca Sanz; Anna M Lithgow; Joaquín R Morán; Ángel L Fuentes de Arriba; Victoria Alcázar

doi:10.1021/acs.orglett.9b04379

Highly Enantioselective Extraction of Phenylglycine by a Chiral Macrocyclic Receptor Based on Supramolecular Interactions

Org Lett. 2020 Feb 7;22(3):867-872. doi: 10.1021/acs.orglett.9b04379. Epub 2020 Jan 13.

Authors

María G Turiel¹, José J Garrido-González¹, Luis Simón¹, Francisca Sanz², Anna M Lithgow³, Joaquín R Morán¹, Ángel L Fuentes de Arriba¹, Victoria Alcázar⁴

Affiliations

¹ Organic Chemistry Department , University of Salamanca , Plaza de los Caídos 1-5 , Salamanca E-37008 , Spain.
² X-Ray Diffraction Service , University of Salamanca , Plaza de los Caídos 1-5 , Salamanca E-37008 , Spain.
³ Nucleus Platform NMR Service , University of Salamanca , Plaza de los Caídos, 1-5 , Salamanca E-37008 , Spain.
⁴ Department of Chemical and Environmental Engineering , Polytechnical University of Madrid , C/José Gutiérrez Abascal 2 , Madrid E-28006 , Spain.

PMID: 31928015
DOI: 10.1021/acs.orglett.9b04379

Abstract

Using supramolecular interactions, a novel macrocyclic receptor is able to selectively extract zwitterionic phenylglycine from neutral aqueous solutions into chloroform with up to 91.8% ee. Modeling studies, nuclear magnetic resonance experiments, and X-ray diffraction analysis were carried out to explain the high enantioselectivity observed.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Chloroform / chemistry
Crystallography, X-Ray
Glycine / analogs & derivatives*
Glycine / chemistry
Glycine / isolation & purification
Macrocyclic Compounds / chemistry*
Models, Molecular
Molecular Structure
Stereoisomerism

Substances

Macrocyclic Compounds
2-phenylglycine
Chloroform
Glycine