Katayama Hidekazu, Mukainakano Takafumi, Kogure Junya, Ohira Tsuyoshi
Department of Applied Biochemistry, School of Engineering, Tokai University, Hiratsuka, Japan.
Department of Biological Sciences, Faculty of Science, Kanagawa University, Hiratsuka, Japan.
J Pept Sci. 2018 Dec;24(12):e3132. doi: 10.1002/psc.3132. Epub 2018 Oct 22.
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.
在胰岛素家族肽中，除了六个保守的半胱氨酸残基外，有时还能在无脊椎动物胰岛素样肽（ILP）中发现另外两个半胱氨酸残基，尽管这种具有四个二硫键的ILP的合成方法尚未完全确立。在本研究中，我们通过使用四个正交的半胱氨酸保护基团进行区域选择性二硫键形成反应，合成了一种具有四个二硫键的甲壳类胰岛素样雄激素腺因子。其二硫键异构体也可以通过相同的方法合成，这表明本研究中开发的合成策略可能对其他具有四个二硫键的ILP的合成有用。
