title: Long-range intramolecular S → N acyl migration: a study of the formation of native peptide analogues via 13-, 15-, and 16-membered cyclic transition states.
abstract: The intramolecular long-range S → N acyl migration via 13-, 15-, and 16-membered cyclic transition states to form native tetra- and pentapeptide analogues was studied on S-acylcysteine peptides containing β- or γ-amino acids. The pH-dependency study of the acyl migration via a 15-membered cyclic transition state indicated that the reaction is favored at a pH range from 7.0 to 7.6. Experimental observations are supported by structural and computational investigations.
authors.affiliation: Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA.
authors.forename: Khanh
authors.initials: K
authors.lastname: Ha
authors.forename: Mamta
authors.initials: M
authors.lastname: Chahar
authors.forename: Jean-Christophe M
authors.initials: JC
authors.lastname: Monbaliu
authors.forename: Ekaterina
authors.initials: E
authors.lastname: Todadze
authors.forename: Finn K
authors.initials: FK
authors.lastname: Hansen
authors.forename: Alexander A
authors.initials: AA
authors.lastname: Oliferenko
authors.forename: Charles E
authors.initials: CE
authors.lastname: Ocampo
authors.forename: David
authors.initials: D
authors.lastname: Leino
authors.forename: Aaron
authors.initials: A
authors.lastname: Lillicotch
authors.forename: Christian V
authors.initials: CV
authors.lastname: Stevens
authors.forename: Alan R
authors.initials: AR
authors.lastname: Katritzky
mesh_terms: D000595:Amino Acid Sequence; D039301:Computers, Molecular; D003545:Cysteine / Q000737:chemistry*; D015394:Molecular Structure; D009842:Oligopeptides / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*
chemical_list: D009842:Oligopeptides; D010455:Peptides; D003545:Cysteine