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Physical Chemistry of Cold Gas-Phase Functional Molecules and Clusters pp 63–87Cite as

Chirality Effects in Jet-Cooled Cyclic Dipeptides

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Abstract

Jet-cooled bichromophoric cyclic dipeptides built on a diketopiperazine (DKP) ring are studied by combining conformer-specific vibrational spectroscopy with quantum chemical calculations. The dependence of the c-LL and c-LD dipeptides structure upon relative absolute configuration, L or D, of the residues is investigated for two residues: phenylalanine (Phe) and tyrosine (Tyr). A folded-extended structure is systematically observed for all systems, like in solution or in the solid. This structure is stabilized by NH…π and CH…π interactions and shows limited stereoselectivity; the only difference between c-LL and c-LD is the nature of the CH…π interaction—Cα…π in c-LD and Cβ…π in c-LL—and a stronger NH…π interaction in c-LD. For all the species studied, the electronic excitation and the charge in the radical cation are localized on the extended ring. The c-LL diastereomer of cyclo di-tyrosyl stands out by the existence of a stacked structure, in which formation of an OH…O hydrogen bond stabilizes parallel aromatic rings orientation. In this structure, the electronic excitation and the major part of the charge in the cation are localized on the H-bond donor. The OH…O H-bond is possible in c-LL and not c-LD, which explains the high stereoselectivity.

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  1. Institut des Sciences Moléculaires d’Orsay (ISMO), CNRS, Univ. Paris-Sud, Université Paris-Saclay, 91405, Orsay, France

    Ariel Pérez-Mellor & Anne Zehnacker

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  1. Ariel Pérez-Mellor
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  2. Anne Zehnacker
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  1. Hiroshima University, Higashi-hiroshima, Japan

    Takayuki Ebata

  2. Tokyo Institute of Technology, Yokohama, Japan

    Masaaki Fujii

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Pérez-Mellor, A., Zehnacker, A. (2019). Chirality Effects in Jet-Cooled Cyclic Dipeptides. In: Ebata, T., Fujii, M. (eds) Physical Chemistry of Cold Gas-Phase Functional Molecules and Clusters. Springer, Singapore. https://doi.org/10.1007/978-981-13-9371-6_3

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