Chemical Synthesis of Human Insulin-Like Peptide-6

Wu Fangzhou; Mayer John P.; Zaykov Alexander N.; Zhang Fa; Liu Fa; DiMarchi Richard D.

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Chemical Synthesis of Human Insulin-Like Peptide-6

机译：人胰岛素样肽-6的化学合成

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Human insulin-like peptide-6 (INSL-6) belongs to the insulin superfamily and shares the distinctive disulfide bond configuration of human insulin. In this report we present the first chemical synthesis of INSL-6 utilizing fluorenyl-methyloxycarbonyl-based (Fmoc) solid-phase peptide chemistry and regioselective disulfide bond construction protocols. Due to the presence of an oxidation-sensitive tryptophan residue, two new orthogonal synthetic methodologies were developed. The first method involved the identification of an additive to suppress the oxidation of tryptophan during iodine-mediated S-acetamidomethyl (Acm) deprotection and the second utilized iodine-free, sulfoxide-directed disulfide bond formation. The methodologies presented here offer an efficient synthetic route to INSL-6 and will further improve synthetic access to other multiple-disulfide-containing peptides with oxidation-sensitive residues.

机译：人胰岛素样肽6（INSL-6）属于胰岛素超家族，具有人胰岛素独特的二硫键构型。在本报告中，我们介绍了基于芴基-甲氧羰基（Fmoc）固相肽化学和区域选择性二硫键构建方案的INSL-6的首次化学合成。由于存在对氧化敏感的色氨酸残基，因此开发了两种新的正交合成方法。第一种方法涉及鉴定在碘介导的S-乙酰氨基甲基（Acm）脱保护过程中抑制色氨酸氧化的添加剂，第二种方法利用无碘，亚砜导向的二硫键形成。本文介绍的方法学为INSL-6提供了有效的合成途径，并将进一步改善对具有氧化敏感性残基的其他含多二硫键的肽的合成途径。

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《Chemistry: A European journal》 |2016年第28期|共7页
作者
Wu Fangzhou; Mayer John P.; Zaykov Alexander N.; Zhang Fa; Liu Fa; DiMarchi Richard D.;
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chemical synthesis; insulin-like peptides; insulin-super family; peptides; proteins;

机译：化学合成胰岛素样肽胰岛素超家族肽蛋白;

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1. Chemical Synthesis of Human Insulin-Like Peptide-6 [J] . Wu Fangzhou, Mayer John P., Zaykov Alexander N., Chemistry: A European journal . 2016,第28期

机译：人胰岛素样肽-6的化学合成
2. Drosophila insulin-like peptide-6 (dilp6) expression from fat body extends lifespan and represses secretion of Drosophila insulin-like peptide-2 from the brain [J] . Hua Bai Ping Kang Marc Tatar Aging Cell . 2012,第6期

机译：果蝇的果蝇胰岛素样肽6（dilp6）表达延长了寿命并抑制了果蝇胰岛素样肽2从大脑的分泌
3. Growth hormone-releasing peptide-6 increases insulin-like growth factor-I mRNA levels and activates Akt in RCA-6 cells as a model of neuropeptide Y neurones. [J] . Frago LM, Paneda C, Argente J, Journal of neuroendocrinology . 2005,第11期

机译：作为神经肽Y神经元的模型，生长激素释放肽-6增加胰岛素样生长因子-I mRNA水平并激活RCA-6细胞中的Akt。
4. Improvements in the Chemical Synthesis of Insulin-Like Peptides [C] . Panagiota Tsetseni, Aggeliki Karkantzou, Spyros Markos American Peptide Symposium . 2009

机译：胰岛素样肽的化学合成的改善
5. Chemical synthesis and characterizations of novel insulin-like peptides. [D] . Wu, Fangzhou. 2016

机译：新型胰岛素样肽的化学合成和表征。
6. Total Chemical Synthesis of a Heterodimeric Interchain Bis-Lactam-Linked Peptide: Application to an Analogue of Human Insulin-Like Peptide 3 [O] . John Karas, Fazel Shabanpoor, Mohammed Akhter Hossain, 2013

机译：全化学合成的异二聚体链间双内酰胺连接的肽：类人胰岛素样肽3的应用。
7. Total chemical synthesis of a heterodimeric interchain Bis-Lactam-linked peptide: application to an analogue of human insulin-like peptide 3 [O] . Karas J., Shabanpoor F., Hossain M., 2013

机译：异二聚体链间双内酰胺连接肽的总化学合成：应用于人类胰岛素样肽3的类似物

Chemical Synthesis of Human Insulin-Like Peptide-6

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