{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Imani Z"],"funding":["Agence Nationale de la Recherche"],"pagination":["9191-9197"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC8163419"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["11(34)"],"pubmed_abstract":["In addition to the classical N-H⋯O[double bond, length as m-dash]C non-covalent interaction, less conventional types of hydrogen bonding, such as N-H⋯S, may play a key role in determining the molecular structure. In this work, using theoretical calculations in combination with spectroscopic analysis in both gas phase and solution phase, we demonstrate that both these H-bonding modes exist simultaneously in low-energy conformers of capped derivatives of Attc, a thietane α-amino acid. 6-Membered ring inter-residue N-H⋯S interactions (C6<sup>γ</sup>), assisted by hyperconjugation between the thietane ring and the backbone, combine with 5-membered ring intra-residue backbone N-H⋯O[double bond, length as m-dash]C interactions (C5) to provide a C5-C6<sup>γ</sup> feature that stabilizes a planar "],"journal":["Chemical science"],"pubmed_title":["Conformation control through concurrent N-H⋯S and N-H⋯O[double bond, length as m-dash]C hydrogen bonding and hyperconjugation effects."],"pmcid":["PMC8163419"],"funding_grant_id":["ANR-17-CE29-0008","ANR-10-LABX-0039-PALM"],"pubmed_authors":["Le Barbu-Debus K","Mundlapati VR","Mons M","Robin S","Imani Z","Guillot R","Zehnacker A","Aitken DJ","Brenner V","Goldsztejn G","Baltaze JP","Gloaguen E"],"additional_accession":[]},"is_claimable":false,"name":"Conformation control through concurrent N-H⋯S and N-H⋯O[double bond, length as m-dash]C hydrogen bonding and hyperconjugation effects.","description":"In addition to the classical N-H⋯O[double bond, length as m-dash]C non-covalent interaction, less conventional types of hydrogen bonding, such as N-H⋯S, may play a key role in determining the molecular structure. In this work, using theoretical calculations in combination with spectroscopic analysis in both gas phase and solution phase, we demonstrate that both these H-bonding modes exist simultaneously in low-energy conformers of capped derivatives of Attc, a thietane α-amino acid. 6-Membered ring inter-residue N-H⋯S interactions (C6<sup>γ</sup>), assisted by hyperconjugation between the thietane ring and the backbone, combine with 5-membered ring intra-residue backbone N-H⋯O[double bond, length as m-dash]C interactions (C5) to provide a C5-C6<sup>γ</sup> feature that stabilizes a planar ","dates":{"release":"2020-01-01T00:00:00Z","publication":"2020 Aug","modification":"2025-04-19T09:08:23.074Z","creation":"2022-02-10T14:44:48.775Z"},"accession":"S-EPMC8163419","cross_references":{"pubmed":["34123167"],"doi":["10.1039/d0sc03339a"]}}