title: Peptide 2-formylthiophenol esters do not proceed through a Ser/Thr ligation pathway, but participate in a peptide aminolysis to enable peptide condensation and cyclization.
abstract: Peptide thiol salicylaldehyde (SAL) esters unexpectedly do not follow a Ser/Thr ligation pathway to react with peptides containing N-terminal Ser/Thr, but proceed towards a peptide aminolysis in DMSO. The reaction takes place even at a low substrate concentration (1 mM). The method has been successfully used to synthesize several natural cyclic peptides, with a high ratio of monocyclic to dimeric products.
authors.affiliation: Department of Chemistry, State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, China. xuechenl@hku.hk.
authors.forename: Chun Ling
authors.initials: CL
authors.lastname: Tung
authors.forename: Clarence T T
authors.initials: CT
authors.lastname: Wong
authors.forename: Xuechen
authors.initials: X
authors.lastname: Li
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D000595:Amino Acid Sequence; D003500:Cyclization; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D008969:Molecular Sequence Data; D010455:Peptides / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D010636:Phenols / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000588:Amines; D004952:Esters; D010455:Peptides; D010456:Peptides, Cyclic; D010636:Phenols; D013438:Sulfhydryl Compounds; C013243:salicylaldehyde; C042983:thiophenol; D004121:Dimethyl Sulfoxide