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- Title
Chiral and Molecular Recognition through Protonation between Aromatic Amino Acids and Tripeptides Probed by Collision-Activated Dissociation in the Gas Phase.
- Authors
Fujihara, Akimasa; Inoue, Hikaru; Sogi, Masanobu; Tajiri, Michiko; Wada, Yoshinao
- Abstract
Chiral and molecular recognition through protonation was investigated through the collision-activated dissociation (CAD) of protonated noncovalent complexes of aromatic amino acid enantiomers with L-alanine- and L-serine-containing tripeptides using a linear ion trap mass spectrometer. In the case of L-alanine-tripeptide (AAA), NH3 loss was observed in the CAD of heterochiral H+(D-Trp)AAA, while H2O loss was the main dissociation pathways for L-Trp, D-Phe, and L-Phe. The protonation site of heterochiral H+(D-Trp)AAA was the amino group of D-Trp, and the NH3 loss occurred from H+(D-Trp). The H2O loss indicated that the proton was attached to the L-alanine tripeptide in the noncovalent complexes. With the substitution of a central residue of L-alanine tripeptide to L-Ser, ASA recognized L-Phe by protonation to the amino group of L-Phe in homochiral H+(L-Phe)ASA. For the protonated noncovalent complexes of His enantiomers with tripeptides (AAA, SAA, ASA, and AAS), protonated His was observed in the spectra, except for those of heterochiral H+(D-His)SAA and H+(D-His)AAS, indicating that D-His did not accept protons from the SAA and AAS in the noncovalent complexes. The amino-acid sequences of the tripeptides required for the recognition of aromatic amino acids were determined by analyses of the CAD spectra.
- Subjects
PROTON transfer reactions; AROMATIC amino acid decarboxylases; ENANTIOMERS; MOLECULAR evolution; CHIRALITY
- Publication
Molecules, 2018, Vol 23, Issue 1, p162
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules23010162