title: Microwave-assisted chemical ligation of S-acyl peptides containing non-terminal cysteine residues.
abstract: An efficient approach for the synthesis of a series of S-acyl peptides containing internal cysteine residues has been developed and the chemical long-range ligation of these S-acyl peptides via 5-, 8-, 11- and 14-membered cyclic transition states has been investigated. Our results include the first examples of successful isopeptide ligations starting from S-acyl peptides containing non-terminal cysteine residues and indicate that the cyclic transition states studied in this present paper are decreasingly favored in the order of their sizes 5≫14>11≫8.
authors: Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA.
authors: Finn K
authors: FK
authors: Hansen
authors: Khanh
authors: K
authors: Ha
authors: Ekaterina
authors: E
authors: Todadze
authors: Aaron
authors: A
authors: Lillicotch
authors: Alexander
authors: A
authors: Frey
authors: Alan R
authors: AR
authors: Katritzky
mesh_terms: D000215:Acylation; D003545:Cysteine / Q000737:chemistry; D008872:Microwaves; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis*
chemical_list: D010455:Peptides; D003545:Cysteine