Crustacean insulin‐like androgenic gland factor (IAG) of Macrobrachium rosenbergii, a heterodimeric peptide having both four disulfide bonds and an N‐linked glycan, was synthesized by the combination of solid‐phase peptide synthesis and the regioselective disulfide formation reactions. The disulfide isomer of IAG could also be synthesized by the same manner. The conformational analysis of these peptides by circular dichroism (CD) spectral measurement indicated that the disulfide bond arrangement affected the peptide conformation in IAG. On the other hand, the N‐linked glycan attached at A chain showed no effect on CD spectra of IAG. This is the first report for the chemical synthesis of insulin‐like heterodimeric glycopeptide having three interchain disulfides, and the synthetic strategy shown here might be useful for the synthesis of other glycosylated four‐disulfide insulin‐like peptides.

中文翻译：

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从淡水虾罗氏沼虾化学合成N-糖基化胰岛素样雄激素腺因子。

罗氏沼虾（Macrobrachium rosenbergii）的甲壳类胰岛素样雄激素腺因子（IAG）是通过固相肽合成和区域选择性二硫键形成反应相结合而合成的，具有两个四个二硫键和一个N-连接的聚糖。IAG的二硫键异构体也可以通过相同的方式合成。通过圆二色性（CD）光谱测量对这些肽进行的构象分析表明，二硫键排列影响了IAG中的肽构象。另一方面，N连接在A链上的连接聚糖对IAG的CD谱没有影响。这是关于化学合成具有三个链间二硫键的胰岛素样异二聚糖肽的第一份报告，此处显示的合成策略可能对其他糖基化的四硫键胰岛素样肽的合成有用。