title: The application of an aryl hydrazine linker prevents beta-elimination side products in the SPPS of C-terminal cysteine peptides.
abstract: Solid-phase synthesis allows for the preparation of some complex cysteine-containing peptides with both a high yield and purity. However, side reactions during chain elongation such as modification of amino acid residues have been found in C-terminal cysteine peptides. We identified 3-(1-piperidinyl)-alanine peptides, corroborated the mechanism of the side reaction, and introduced an efficient approach for the Fmoc-based synthesis of C-terminal cysteine peptides using an aryl hydrazine linker.
authors.affiliation: Center for Drug Discovery, China Pharmaceutical University, Nanjing, China.
authors.forename: Shuaijian
authors.initials: S
authors.lastname: Ni
authors.forename: Huibin
authors.initials: H
authors.lastname: Zhang
authors.forename: Wenlong
authors.initials: W
authors.lastname: Huang
authors.forename: Jinpei
authors.initials: J
authors.lastname: Zhou
authors.forename: Hai
authors.initials: H
authors.lastname: Qian
authors.forename: Wei
authors.initials: W
authors.lastname: Chen
mesh_terms: D000409:Alanine / Q000737:chemistry; D000595:Amino Acid Sequence; D003545:Cysteine / Q000737:chemistry*; D006834:Hydrazines / Q000737:chemistry*; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D006834:Hydrazines; D010455:Peptides; C029424:hydrazine; D003545:Cysteine; D000409:Alanine