The application of an aryl hydrazine linker prevents beta-elimination side products in the SPPS of C-terminal cysteine peptides.
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.
Ni
Shuaijian
S
Center for Drug Discovery, China Pharmaceutical University, Nanjing, China.
Zhang
Huibin
H
Huang
Wenlong
W
Zhou
Jinpei
J
Qian
Hai
H
Chen
Wei
W
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
D006834:Hydrazines; D010455:Peptides; C029424:hydrazine; D003545:Cysteine; D000409:Alanine