title: Serine/threonine ligation for the chemical synthesis of proteins.
abstract: Advances in the development of efficient peptide ligation methods have enabled the total synthesis of complex proteins to be successfully undertaken. Recently, a Ser/Thr ligation has emerged as a new tool in synthetic protein chemistry. The chemoselective reaction between an N-terminal serine or threonine of an unprotected peptide segment and a C-terminal salicylaldehyde ester of another unprotected peptide segment gives rise to an N,O-benzylidene acetal linked product, which upon acidolysis produces a native peptide bond at the site of ligation. Ser/Thr ligation has been used for the synthesis of the human erythrocyte acylphosphatase protein and MUC1 glycopeptide segments, semisynthesis of peptoid/PEG-RNase S protein hybrids, and cyclic peptide synthesis including cyclic tetrapeptides, cyclomontanin B, yunnanin C, mahafacyclin B, and daptomycin.
authors.affiliation: Department of Chemistry, The University of Hong Kong, Hong Kong, China.
authors.forename: Chi Lung
authors.initials: CL
authors.lastname: Lee
authors.affiliation: Department of Chemistry, The University of Hong Kong, Hong Kong, China; The State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Hong Kong, China. Electronic address: xuechenl@hku.hk.
authors.forename: Xuechen
authors.initials: X
authors.lastname: Li
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D000595:Amino Acid Sequence; D000818:Animals; D003500:Cyclization; D006801:Humans; D008958:Models, Molecular; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000737:chemistry; D011506:Proteins / Q000138:chemical synthesis* / Q000737:chemistry; D012694:Serine / Q000138:chemical synthesis / Q000737:chemistry*; D013912:Threonine / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D010455:Peptides; D010456:Peptides, Cyclic; D011506:Proteins; C013243:salicylaldehyde; D013912:Threonine; D012694:Serine