Conformation control through concurrent N–H⋯S and N–H⋯OC hydrogen bonding and hyperconjugation effects
Zeynab Imani, Venkateswara Rao Mundlapati, Gildas Goldsztejn, Valérie Brenner, Eric Gloaguen, Régis Guillot, Jean‐Pierre Baltaze, Katia Le Barbu‐Debus, Sylvie Robin, Anne Zehnacker, Michel Mons, David J. Aitken
Abstract
In addition to N–H⋯OC bonds, less conventional N–H⋯S hydrogen bonds are found to stabilize extended backbone geometries in derivatives of a thietane α-amino acid, providing a promising tool for the design of new peptidomimetic architectures.
Topics & Concepts
HyperconjugationHydrogen bondPeptidomimeticChemistryStereochemistryMoleculeOrganic chemistryPeptideBiochemistryChemical Synthesis and AnalysisCrystallography and molecular interactionsSynthesis and Catalytic Reactions