title: Oxyazapeptides: synthesis, structure determination, and conformational analysis.
abstract: Herein we report the synthesis, X-ray structure determination, and conformational analysis of a novel class of heteroatom-modified peptidomimetics, which we shall call "oxyazapeptides". Substituting the typical native N-C(α) bond with an O-N(α) bond creates a completely new, previously unknown family of peptidomimetics, which are hydrolytically stable and display very interesting conformational behavior. Force field calculations revealed that the barrier to rotation around the O-N(α) bond in oxyazapeptides is five times lower than that around the N-N(α) bond in azapeptides. Also, conformational analysis supported by X-ray suggests that the oxyaza moiety can effectively induce β-turns, which can make the newly discovered oxyazapeptide scaffold a useful tool for drug discovery and for design of biologics.
authors.affiliation: Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA.
authors.forename: Suvendu
authors.initials: S
authors.lastname: Biswas
authors.forename: Nader E
authors.initials: NE
authors.lastname: Abo-Dya
authors.forename: Alexander
authors.initials: A
authors.lastname: Oliferenko
authors.forename: Amir
authors.initials: A
authors.lastname: Khiabani
authors.forename: Peter J
authors.initials: PJ
authors.lastname: Steel
authors.forename: Khalid A
authors.initials: KA
authors.lastname: Alamry
authors.forename: Alan R
authors.initials: AR
authors.lastname: Katritzky
mesh_terms: D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D001372:Aza Compounds; D010455:Peptides