Enantioselective Complexation of Protonated Tyrosine by a Chiral Crown-ether: The Nature of the Hydrogen Bonds Makes the Difference.

Autor: Vo KX; School of Life Science and Technology, Institute of Science Tokyo, 4259 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa, 226-8503, Japan., Hirata K; Department of Chemistry, School of Science, Institute of Science Tokyo, 2-12-1 Ookayama, Meguro-ku, Tokyo, 152-8550, Japan., Martínez-Haya B; Center for Nanoscience and Sustainable Technologies, Universidad Pablo de Olavide, E-41013, Seville, Spain., Oomens J; FELIX Laboratory, Institute for Molecules and Materials, Radboud University, Toernooiveld 7, NL-6525 ED, Nijmegen, The Netherlands., Ishiuchi SI; Department of Chemistry, School of Science, Institute of Science Tokyo, 2-12-1 Ookayama, Meguro-ku, Tokyo, 152-8550, Japan., Fujii M; Laboratory for Chemistry and Life Science, Institute of Innovative Research, Institute of Science Tokyo, 4259 Nagatsuta-cho, Midori-ku, Yokohama, 226-8503, Japan.; International Research Frontiers Initiative (IRFI), Institute of Innovative Research, Institute of Science Tokyo, 4259 Nagatsuta-cho, Midori-ku, Yokohama, Japan.; Research and Development Initiative, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo, 112-8551, Japan., Zehnacker A; International Research Frontiers Initiative (IRFI), Institute of Innovative Research, Institute of Science Tokyo, 4259 Nagatsuta-cho, Midori-ku, Yokohama, Japan.; Institut des Sciences Moléculaires d'Orsay (ISMO), CNRS, Université Paris-Saclay, F-91405, Orsay, France.
Jazyk: angličtina
Zdroj: Chemphyschem : a European journal of chemical physics and physical chemistry [Chemphyschem] 2024 Nov 15, pp. e202400880. Date of Electronic Publication: 2024 Nov 15.
DOI: 10.1002/cphc.202400880
Abstrakt: The complexes formed between (18-crown-6)-tetracarboxylic acid, denoted as 18C6TA, and the two enantiomers of protonated tyrosine, L- and D-Tyr, are studied in a cryogenic ion trap by combining mass spectrometry, laser spectroscopy, and DFT calculations. Both UV and IR photodissociation spectra indicate the formation of multiple isomers for each complex, some of them interconverting upon IR irradiation. Conformer-selective vibrational spectroscopy reveals that all structures involve an internally hydrogen-bonded folded structure of the crown ether. The complexes formed with L-Tyr involve two NH…O interactions with the ether oxygen atoms, accompanied by two hydrogen bonds to the crown ether carboxylic function, one from the NH group and the other from the COOH group of tyrosine. The complexes formed with D-Tyr show more conformational mobility: two out of the three lowest energy conformers observed are tripodal, with three NH…O interactions between the amino acid ammonium and the crown ether oxygens. An additional conformer shows only one NH…O interaction, but has two interactions involving one of the cavity COOH moieties, one with the NH and one with the phenol OH. The increased calculated stability of the complex made from (-) 18C6TA and L-Tyr parallels its higher abundance in the mass spectrum of an isotopically labelled racemic mixture.
(© 2024 The Author(s). ChemPhysChem published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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