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Molecules 2018, 23(1), 162; https://doi.org/10.3390/molecules23010162

Chiral and Molecular Recognition through Protonation between Aromatic Amino Acids and Tripeptides Probed by Collision-Activated Dissociation in the Gas Phase

1
Department of Chemistry, Osaka Prefecture University, Osaka 599-8531, Japan
2
Department of Molecular Medicine, Osaka Women’s and Children’s Hospital, Osaka 594-1101, Japan
*
Author to whom correspondence should be addressed.
Received: 6 December 2017 / Revised: 6 January 2018 / Accepted: 11 January 2018 / Published: 13 January 2018
(This article belongs to the Special Issue Recent Advances in Chiroptical Spectroscopy)
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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. View Full-Text
Keywords: chemical evolution; molecular clouds; enantiomeric excess; homochirality chemical evolution; molecular clouds; enantiomeric excess; homochirality
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).
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Fujihara, A.; Inoue, H.; Sogi, M.; Tajiri, M.; Wada, Y. Chiral and Molecular Recognition through Protonation between Aromatic Amino Acids and Tripeptides Probed by Collision-Activated Dissociation in the Gas Phase. Molecules 2018, 23, 162.

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