Chemical synthesis of the crustacean insulin‐like peptide with four disulfide bonds

March 6, 2019

Title

Chemical synthesis of the crustacean insulin‐like peptide with four disulfide bonds

Author

Hidekazu Katayama, Takafumi Mukainakano, Junya Kogure, Tsuyoshi Ohira

Year

2018

Journal

Journal of Peptide Science

Abstract

Among the insulin‐family peptides, two additional cysteine residues other than six conserved cysteines are sometimes found in invertebrate insulin‐like peptides (ILPs), although the synthetic method for such four disulfide ILPs has not yet been well established. In this study, we synthesized a crustacean insulin‐like androgenic gland factor with four disulfides by the regioselective disulfide bond formation reactions using four orthogonal Cys‐protecting groups. Its disulfide isomer could be also synthesized by the same method, indicating that the synthetic strategy developed in this study might be useful for the synthesis of other four disulfide ILPs.

Instrument

J-820

Keywords

Circular dichroism, Secondary structure, Biochemistry