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Elucidating the multiple structures of pipecolic acid by rotational spectroscopy

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Abstract

The complex conformational space of the non-proteinogenic cyclic amino acid pipecolic acid has been explored in the gas phase for the first time. Solid pipecolic acid samples were vaporized by laser ablation and expanded in a supersonic jet where the rotational spectral signatures owing to nine different conformers were observed by Fourier transform microwave spectroscopy. All species were identified by comparison of the experimental rotational and nuclear quadrupole coupling constants with those predicted theoretically. Observation of type-III conformers, leading to a difference when compared against the conformational behavior of the analog amino acid proline, has been interpreted by an increment in steric hindrance when increasing the number of carbons present in the ring.

Graphical abstract: Elucidating the multiple structures of pipecolic acid by rotational spectroscopy

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Publication details

The article was received on 29 Sep 2018, accepted on 25 Nov 2018 and first published on 26 Nov 2018


Article type: Paper
DOI: 10.1039/C8CP06120C
Citation: Phys. Chem. Chem. Phys., 2019, Advance Article
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    Elucidating the multiple structures of pipecolic acid by rotational spectroscopy

    A. Simão, C. Cabezas, I. León, E. R. Alonso, S. Mata and J. L. Alonso, Phys. Chem. Chem. Phys., 2019, Advance Article , DOI: 10.1039/C8CP06120C

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