1426326-86-4Relevant academic research and scientific papers
Peptide Head-to-Tail Cyclization: A “Molecular Claw” Approach
Yamagami, Sayuri,Okada, Yohei,Kitano, Yoshikazu,Chiba, Kazuhiro
, p. 3133 - 3138 (2021)
Both naturally occurring and artificial cyclic peptides are in high demand for a wide range of therapeutic applications due to the improvement of their enzymatic stability, cell permeability, and pharmacological activity compared to their linear counterparts. Among the simplest yet challenging cyclizations is the head-to-tail fashion, where linear peptides are cyclized via C- and N-termini, since most current peptide synthesis has been dominated by the use of C-terminal protecting supports. Herein, we demonstrate that a soluble-tag-assisted liquid-phase peptide synthesis in combination with a backbone amide linker strategy is applicable to the head-to-tail cyclization. The use of an amide “N-tag” instead of the general terminal C-tag enables an effective head-to-tail cyclization on-support. The key for successful cyclization is a tagging position that enables the center of the peptide to be grabbed.
Soluble tag-assisted peptide head-to-tail cyclization: Total synthesis of mahafacyclin B
Fujita, Yuko,Fujita, Shuji,Okada, Yohei,Chiba, Kazuhiro
supporting information, p. 1155 - 1157 (2013/05/09)
A soluble tag-assisted liquid-phase method was successfully applied to peptide head-to-tail cyclization, leading to the total synthesis of antimalarial cyclic heptapeptide, mahafacyclin B (1). The cyclization was carried out in the liquid phase with the tag remaining, which allowed rapid reaction workup and product isolation.
