title: Peptidyl N,N-bis(2-mercaptoethyl)-amides as thioester precursors for native chemical ligation.
abstract: With two β-mercaptoethyl groups on the N, a tertiary amide of structure 1 is always poised for intramolecular thioesterification however it flips about the C-N bond. It is shown that a peptide with such a C-terminal N,N-bis(2-mercaptoethyl)-amide (BMEA) can be used directly for native chemical ligation (NCL). These BMEA peptides are easily prepared with standard Fmoc-solid phase peptide synthesis protocols, thus giving a very convenient access to the thioester components for NCL.
authors.affiliation: Division of Chemical Biology and Biotechnology, School of Biological Sciences, Nanyang Technological University, 60 Nanyang Drive, Singapore 637551.
authors.forename: Wen
authors.initials: W
authors.lastname: Hou
authors.forename: Xiaohong
authors.initials: X
authors.lastname: Zhang
authors.forename: Fupeng
authors.initials: F
authors.lastname: Li
authors.forename: Chuan-Fa
authors.initials: CF
authors.lastname: Liu
mesh_terms: D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000577:Amides; D004952:Esters; D010455:Peptides; D013457:Sulfur Compounds