NDLI: Lariat ethers in the chiral recognition of amino acid esters:electrospray ionization mass spectrometry investigation

Content Provider	Springer Nature Link
Author	Bredikhina, Zemfira A. Sharafutdiva, Dilyara R. Bazava, Olga B. Babaev, Vasily M. Fayzullin, Robert R. Rizvav, Ildar Kh. Bredikhin, Alexander A.
Copyright Year	2014
Abstract	The ability of the crown ethers (1–4), containing the ortho- or para- methoxyphenoxy-methyl substituents in their structure, to chiral recognition in reference to amino acid esters has been investigated by electrospray ionization mass spectrometry (ESI-MS). The method allows registering the diastereomeric complexes between the studied crowns as hosts and the protonated alanine, phenylglycine and phenylalanine methyl esters as guests in the gas phase. ESI-MS experiments using isotopically labeled guests provide robust and reproducible results, indicating a moderate degree of chiral discrimination in the series of the studied crown ethers. ESI-MS experiments using achiral amine as a reference yielded the results comparable with the previous method. It has been found that (S)-enantiomers of the crowns bind predominately (S)-enantiomers of the amino acid esters, and vice-versa. It has been shown that the chiral ortho-substituted crown (S)-1 demonstrates the more pronounced values for chiral discrimination as compared with the para-substituted crown (S)-2. This fact indicates the interrelationship between the chiral recognition and the lariat nature of crown 1. Increasing the size of the cavity and the presence of a flat aromatic moiety in crowns 3 and 4 strengthens their complexing ability, simultaneously weakening the enantioselectivity of the complexation.
Starting Page	417
Ending Page	426
Page Count	10
File Format	PDF
ISSN	13883127
Journal	Journal of Inclusion Phenomena and Macrocyclic Chemistry
Volume Number	80
Issue Number	3-4
e-ISSN	15731111
Language	English
Publisher	Springer Netherlands
Publisher Date	2014-07-05
Publisher Place	Dordrecht
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Crown ethers Amino acids Host-guest chemistry Chiral recognition Lariat effect Electrospray ionization Organic Chemistry Food Science Crystallography
Content Type	Text
Resource Type	Article
Subject	Chemistry Condensed Matter Physics Food Science

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