title: Tandem thiol switch synthesis of peptide thioesters via N-S acyl shift on thiazolidine.
abstract: An efficient "thiol switch" approach for the synthesis of peptide thioesters via an acid-catalyzed N-S acyl shift and a thioester exchange reaction in tandem with concurrent removal of protecting groups is described. This method employs novel 2-(thiomethyl)thiazolidine (TMT)-anchored resins and is fully compatible with Fmoc chemistry.
authors: School of Biological Sciences, Nanyang Technological University, 60 Nanyang Drive, Singapore 637551.
authors: Rohit K
authors: RK
authors: Sharma
authors: James P
authors: JP
authors: Tam
mesh_terms: D000215:Acylation; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D010455:Peptides / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry; D053778:Thiazolidines / Q000737:chemistry*
chemical_list: D004952:Esters; D010455:Peptides; D013438:Sulfhydryl Compounds; D053778:Thiazolidines; D013455:Sulfur; D009584:Nitrogen