Chiral discrimination between tyrosine and -cyclodextrin revealed by cryogenic ion trap infrared spectroscopy - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Physical Chemistry Chemical Physics Année : 2020

Chiral discrimination between tyrosine and -cyclodextrin revealed by cryogenic ion trap infrared spectroscopy

Keisuke Hirata
Yuta Mori
  • Fonction : Auteur
Shun-Ichi Ishiuchi
  • Fonction : Auteur
Masaaki Fujii
  • Fonction : Auteur

Résumé

Complexes of permethylated -cyclodextrin (-MCD) with the two enantiomers of protonated tyrosine (L-and D-TyrH +) are studied by cryogenic ion trap infrared photo-dissociation spectroscopy. The vibrational spectra in the OH/NH stretch and fingerprint regions are assigned based on density functional theory calculations. The spectrum of both Land D-TyrH + complexes contains features characteristic of a first structure with ammonium and acid groups of the amino acid simultaneously interacting with the -MCD, the phenolic OH remaining free. A second structure involving additional interaction between the phenolic OH and the -MCD is observed only for the complex with D-TyrH +. The larger abundance of the D-TyrH + complex in the mass spectrum is tentatively explained in terms of (1) better insertion of D-TyrH + within the cavity with the hydrophobic aromatic moiety less exposed to hydrophilic solvent molecules and (2) a stiff structure involving three interaction points, namely the ammonium, the phenolic OH and the carboxylic acid OH, which is not possible for the complex with L-TyrH +. The recognition process does not occur through size effects that induce complementarity to the host molecule but specific interactions. These results provide a comprehensive understanding of how the cyclodextrin recognises a chiral biomolecule. 2
Fichier principal
Vignette du fichier
Article_CD_HAL.pdf (1.08 Mo) Télécharger le fichier
Origine : Fichiers produits par l'(les) auteur(s)
Loading...

Dates et versions

hal-02993740 , version 1 (07-11-2020)

Identifiants

Citer

Keisuke Hirata, Yuta Mori, Shun-Ichi Ishiuchi, Masaaki Fujii, Anne Zehnacker. Chiral discrimination between tyrosine and -cyclodextrin revealed by cryogenic ion trap infrared spectroscopy. Physical Chemistry Chemical Physics, 2020, ⟨10.1039/d0cp02968h⟩. ⟨hal-02993740⟩
14 Consultations
106 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More