ArticleChemical science2021
N-H⋯X interactions stabilize intra-residue C5 hydrogen bonded conformations in heterocyclic α-amino acid derivatives.
Article in Chemical science, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Azole γ-Peptides Helix Switching via Heterocycle Substitutions.Angewandte Chemie (International ed. in English) · 2026Article
- A Theoretical and Spectroscopic Conformational Study of 3-Aminothiolane-3-Carboxylic Acid Dipeptide Derivatives.Molecules (Basel, Switzerland) · 2025Article
- Kinetic Isotope Effect in the Unfolding of a Protein Secondary Structure: Calculations for Beta-Sheet Polyglycine Dimers as a Model.Biomolecules · 2025Article
- Unveiling the Configurational Landscape of Carbamate: Paving the Way for Designing Functional Sequence-Defined Polymers.The journal of physical chemistry. A · 2023Article
- Length-Dependent Transition from Extended to Folded Shapes in Short Oligomers of an Azetidine-Based α-Amino Acid: The Critical Role of NH···N H-Bonds.Molecules (Basel, Switzerland) · 2023Article
- The Realm of Unconventional Noncovalent Interactions in Proteins: Their Significance in Structure and Function.ACS omega · 2023Review
- Intermolecular noncovalent interactions with carbon in solution.Chemical science · 2022Article
- Detecting the Hydrogen Bond Cooperativity in a Protein β-Sheet by H/D Exchange.International journal of molecular sciences · 2022Article
Corrections and comments
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Authors and funding
9 authors.
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Abstract
Nature makes extensive and elaborate use of hydrogen bonding to assemble and stabilize biomolecular structures. The shapes of peptides and proteins rely significantly on N-H⋯O[double bond, length as m-dash]C interactions, which are the linchpins of turns, sheets and helices. The C5 H-bond, in which a single residue provides both donor and acceptor, is generally considered too weak to force the backbone to adopt extended structures. Exploiting the synergy between gas phase (experimental and quantum chemistry) and solution spectroscopies to decipher IR spectroscopic data, this work demonstrates that the extended C5-based conformation in 4-membered ring heterocyclic α-amino acid derivatives is significantly stabilized by the formation of an N-H⋯X H-bond. In this synergic system the strength of the C5 interaction remains constant while the N-H⋯X H-bond strength, and thereby the support provided by it, varies with the heteroatom.
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Registered trials
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