title: Accessing the disallowed conformations of peptides employing amide-to-imidate modification.
abstract: Selective modification of the C-terminal amide in peptides to dihydrooxazine (a novel stable imidate isostere) by intramolecular nucleophilic cyclo-O-alkylation of the corresponding N-(3-bromopropyl)amides results in constraining of the C-terminal residue in natively disallowed conformations both in crystals and in solution.
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, CV Raman Avenue, Bangalore, India 560012.
authors.forename: Damodara N
authors.initials: DN
authors.lastname: Reddy
authors.forename: Ravula
authors.initials: R
authors.lastname: Thirupathi
authors.forename: Erode N
authors.initials: EN
authors.lastname: Prabhakaran
mesh_terms: D000577:Amides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007096:Imidoesters / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D017434:Protein Structure, Tertiary; D012996:Solutions / Q000737:chemistry
chemical_list: D000577:Amides; D007096:Imidoesters; D010455:Peptides; D012996:Solutions