title: N-Linked Glycosyl Auxiliary-Mediated Native Chemical Ligation on Aspartic Acid: Application towards N-Glycopeptide Synthesis.
abstract: A practical approach towards N-glycopeptide synthesis using an auxiliary-mediated dual native chemical ligation (NCL) has been developed. The first NCL connects an N-linked glycosyl auxiliary to the thioester side chain of an N-terminal aspartate oligopeptide. This intermediate undergoes a second NCL with a C-terminal thioester oligopeptide. Mild cleavage provides the desired N-glycopeptide.
authors.affiliation: School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371, Singapore.
authors.forename: Hua
authors.initials: H
authors.lastname: Chai
authors.affiliation: School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371, Singapore.
authors.forename: Kim
authors.initials: K
authors.lastname: Le Mai Hoang
authors.affiliation: School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371, Singapore.
authors.forename: Minh Duy
authors.initials: MD
authors.lastname: Vu
authors.affiliation: School of Biological Sciences, Nanyang Technological University, 60 Nanyang Drive, Singapore, 637551, Singapore.
authors.forename: Kalyan
authors.initials: K
authors.lastname: Pasunooti
authors.affiliation: School of Biological Sciences, Nanyang Technological University, 60 Nanyang Drive, Singapore, 637551, Singapore.
authors.forename: Chuan-Fa
authors.initials: CF
authors.lastname: Liu
authors.affiliation: School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371, Singapore. xuewei@ntu.edu.sg.
authors.forename: Xue-Wei
authors.initials: XW
authors.lastname: Liu
mesh_terms: D001224:Aspartic Acid / Q000737:chemistry*; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation
chemical_list: D006020:Glycopeptides; D001224:Aspartic Acid
keywords: CTLA-4; N-glycopeptide synthesis; aspartic acid; auxiliary mediation; dual native chemical ligation