title: A thioethylalkylamido (TEA) thioester surrogate in the synthesis of a cyclic peptide via a tandem acyl shift.
abstract: The cyclic cystine-knot peptide, kalata B1, was synthesized by employing a novel Fmoc-compatible thioethylalkylamido (TEA) thioester surrogate via an N-S acyl shift followed by a thiol-thioester exchange reaction. TEA thioester surrogate is cost-effective, conveniently prepared in one-step with starting materials, readily available from commercial sources, and highly efficient in preparing peptide thioesters.
authors.affiliation: School of Biological Sciences, Nanyang Technological University, 60 Nanyang Drive, Singapore 637551.
authors.forename: Misako
authors.initials: M
authors.lastname: Taichi
authors.forename: Xinya
authors.initials: X
authors.lastname: Hemu
authors.forename: Yibo
authors.initials: Y
authors.lastname: Qiu
authors.forename: James P
authors.initials: JP
authors.lastname: Tam
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D047169:Cyclotides / Q000138:chemical synthesis* / Q000737:chemistry; D010455:Peptides / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000577:Amides; D047169:Cyclotides; D010455:Peptides; D010456:Peptides, Cyclic; D013438:Sulfhydryl Compounds; C091930:kalata B1