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Low-Energy Collisions of Protonated Enantiopure Amino Acids with Chiral Target Gases
Stockholm University, Faculty of Science, Department of Physics. SCA R&D Centre, Sweden.ORCID iD: 0000-0002-6770-1595
Stockholm University, Faculty of Science, Department of Physics.
Stockholm University, Faculty of Science, Department of Physics.
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Number of Authors: 62017 (English)In: Journal of the American Society for Mass Spectrometry, ISSN 1044-0305, E-ISSN 1879-1123, Vol. 28, no 12, p. 2686-2691Article in journal (Refereed) Published
Abstract [en]

Here we report on the gas-phase interactions between protonated enantiopure amino acids (l- and d-enantiomers of Met, Phe, and Trp) and chiral target gases [(R)- and (S)-2-butanol, and (S)-1-phenylethanol] in 0.1-10.0 eV low-energy collisions. Two major processes are seen to occur over this collision energy regime, collision-induced dissociation and ion-molecule complex formation. Both processes were found to be independent of the stereo-chemical composition of the interacting ions and targets. These data shed light on the currently debated mechanisms of gas-phase chiral selectivity by demonstrating the inapplicability of the three-point model to these interactions, at least under single collision conditions.

Place, publisher, year, edition, pages
2017. Vol. 28, no 12, p. 2686-2691
Keywords [en]
Collision induced dissociation, Chiral target gases, Chirality, Low-energy collisions, Enantiopure amino acids, Gas-phase complexes
National Category
Physical Sciences Chemical Sciences
Research subject
Physics
Identifiers
URN: urn:nbn:se:su:diva-150878DOI: 10.1007/s13361-017-1796-7ISI: 000416567600016PubMedID: 28936701OAI: oai:DiVA.org:su-150878DiVA, id: diva2:1172551
Available from: 2018-01-10 Created: 2018-01-10 Last updated: 2018-08-27Bibliographically approved
In thesis
1. Interactions of chiral ions and molecules in gas phase: Towards an understanding of chiral recognition mechanism
Open this publication in new window or tab >>Interactions of chiral ions and molecules in gas phase: Towards an understanding of chiral recognition mechanism
2018 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis comprises the research related to interactions of enantiopure amino acids with chiral and achiral molecules in gas phase. The investigation of the mechanism responsible for chiral discrimination is of the special interest in this work. An electrospray ion source platform (Stockholm University), quadrupole time-of-flight mass spectrometer (University of Oslo) and Fourier-transform ion cyclotron resonance mass spectrometer in combination with OPO laser (Centre Laser Infrarouge d'Orsay (CLIO), France)  have been used in our studies. Results of experiments on collisions of enantiopure amino acids, namely phenylalanine (Phe), tryptophan (Trp), and methionine (Met) with chiral and achiral targets in high and low energy regimes are presented. The fragmentation process is discussed in detail and compared with generally accepted models of amino acid fragmentation. Formation of proton bound diastereomeric adducts of amino acid and chiral alcohols (2-butanol and 1-phenylethanol) in single collisions is reported. The emphasis was given to reveal stereochemical effects in above mentioned reactions. The structure and vibrational properties of diastereomeric dimers of tryptophan studied using infrared multiphoton dissociation (IRMPD) spectrometry are presented. Structures and energies of most stable conformers obtained with quantum chemical calculations are described and compared to the experimental data. The stereo-dependent features are underlined and the chiral discrimination using IRMPD is addressed.

Place, publisher, year, edition, pages
Stockholm: Department of Physics, Stockholm University, 2018. p. 76
National Category
Atom and Molecular Physics and Optics
Research subject
Physics
Identifiers
urn:nbn:se:su:diva-159310 (URN)978-91-7797-354-6 (ISBN)978-91-7797-355-3 (ISBN)
Public defence
2018-10-16, sal FB54, AlbaNova universitetscentrum, Roslagstullsbacken 21, Stockholm, 10:00 (English)
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Supervisors
Note

At the time of the doctoral defense, the following papers were unpublished and had a status as follows: Paper 4: Manuscript. Paper 5: Manuscript.

Available from: 2018-09-21 Created: 2018-08-27 Last updated: 2018-09-21Bibliographically approved

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