Novel Chemical Strategy for the Synthesis of RGDCySS Tetrapeptide

doi:10.1007/s40242-014-3228-6

高等学校化学研究 ›› 2014, Vol. 30 ›› Issue (1): 103-107.doi: 10.1007/s40242-014-3228-6

Novel Chemical Strategy for the Synthesis of RGDCySS Tetrapeptide

XU Baofeng², YANG Sen¹, ZHU Jinming³, MA Yudan¹, ZHAO Gang², GUO Yi¹, XU Li¹

1. Key Laboratory for Molecular Enzymology and Engineering, Ministry of Education, College of Life Science, Jilin University, Changchun 130012, P. R. China;
2. Neurosurgery Department of the First Hospital of Jilin University, Changchun 130021, P. R. China;
3. The Second Hospital of Jilin University, Changchun 130041, P. R. China

收稿日期:2013-05-20 修回日期:2013-06-18 出版日期:2014-02-01 发布日期:2013-07-22
通讯作者: GUO Yi,E-mail:guoyi@jlu.edu.cn E-mail:guoyi@jlu.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(No.81271697), the Science Foundation of Changchun City, China(No.09SF02), the China Postdoctoral Science Foundation(No.20100481048), the Specialized Research Fund for the Doctoral Program of Higher Education of China(No.20100061120077) and the Social Development Project of Science and Technology Department of Jilin Province, China(Nos.20106031, 20120967, YYZX2012).

Novel Chemical Strategy for the Synthesis of RGDCySS Tetrapeptide

XU Baofeng², YANG Sen¹, ZHU Jinming³, MA Yudan¹, ZHAO Gang², GUO Yi¹, XU Li¹

1. Key Laboratory for Molecular Enzymology and Engineering, Ministry of Education, College of Life Science, Jilin University, Changchun 130012, P. R. China;
2. Neurosurgery Department of the First Hospital of Jilin University, Changchun 130021, P. R. China;
3. The Second Hospital of Jilin University, Changchun 130041, P. R. China

Received:2013-05-20 Revised:2013-06-18 Online:2014-02-01 Published:2013-07-22
Contact: GUO Yi,E-mail:guoyi@jlu.edu.cn E-mail:guoyi@jlu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.81271697), the Science Foundation of Changchun City, China(No.09SF02), the China Postdoctoral Science Foundation(No.20100481048), the Specialized Research Fund for the Doctoral Program of Higher Education of China(No.20100061120077) and the Social Development Project of Science and Technology Department of Jilin Province, China(Nos.20106031, 20120967, YYZX2012).

摘要/Abstract

摘要：

A new route was described to synthesize Arg-Gly-Asp-X(RGDX, X=amino acid) tetrapeptide. To better understand the method, the tetrapeptide Arg-Gly-Asp-CySS(RGDCySS) was chosen as a model target for X. First, GDCySS was obtained in four steps, comprising the chloroacetylation of L-aspartic acid(ClCH₂COAsp), synthesis of chloroacetyl L-aspartic acid anhydride[ClCH₂COAsp(CO)₂O], formation of ClCH₂COAsp-CySS and ammonolysis of ClCH₂COAsp-CySS. Second, preparation of Arg-NCA, which was coupled with GDCySS to synthesize RGDCySS by the NCA method(Leuchs' anhydrides method, NCA: N-carboxy-α-amino acid anhydride). The purity of the product was analyzed by the high performance liquid chromatography(HPLC). Molecular weights of the peptide products were confirmed by mass spectroscopy. In the developed approach, less protected amino acids were used compared to conventional solid-phase synthesis. The new route offers advantages of low cost, simplicity and rapid synthesis with a reasonable yield of 63.0%(calculated according to arginine content).

关键词: Arg-Gly-Asp(RGD), Arg-Gly-Asp-X(RGDX), Peptide synthesis, Arg-Gly-Asp-CySS(RGDCySS), Chemical method, N-Carboxy-α-amino acid anhydride(NCA)

Abstract:

Key words: Arg-Gly-Asp(RGD), Arg-Gly-Asp-X(RGDX), Peptide synthesis, Arg-Gly-Asp-CySS(RGDCySS), Chemical method, N-Carboxy-α-amino acid anhydride(NCA)

XU Baofeng, YANG Sen, ZHU Jinming, MA Yudan, ZHAO Gang, GUO Yi, XU Li. Novel Chemical Strategy for the Synthesis of RGDCySS Tetrapeptide[J]. 高等学校化学研究, 2014, 30(1): 103-107.

XU Baofeng, YANG Sen, ZHU Jinming, MA Yudan, ZHAO Gang, GUO Yi, XU Li. Novel Chemical Strategy for the Synthesis of RGDCySS Tetrapeptide[J]. Chemical Research in Chinese Universities, 2014, 30(1): 103-107.

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Novel Chemical Strategy for the Synthesis of RGDCySS Tetrapeptide

Novel Chemical Strategy for the Synthesis of RGDCySS Tetrapeptide

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