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Novel chemical strategy for the synthesis of RGDCySS tetrapeptide

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Abstract

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).

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Authors and Affiliations

  1. Key Laboratory for Molecular Enzymology and Engineering, Ministry of Education, College of Life Science, Jilin University, Changchun, 130012, P. R. China

    Sen Yang, Yudan Ma, Yi Guo & Li Xu

  2. Neurosurgery Department of the First Hospital of Jilin University, Changchun, 130021, P. R. China

    Baofeng Xu & Gang Zhao

  3. The Second Hospital of Jilin University, Changchun, 130041, P. R. China

    Jinming Zhu

Authors
  1. Baofeng Xu
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  2. Sen Yang
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  3. Jinming Zhu
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  4. Yudan Ma
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  5. Gang Zhao
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  6. Yi Guo
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  7. Li Xu
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Corresponding author

Correspondence to Yi Guo.

Additional information

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(No.20100061120077) and the Social Development Project of Science and Technology Department of Jilin Province, China(Nos.20106031, 20120967, YYZX2012).

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Xu, B., Yang, S., Zhu, J. et al. Novel chemical strategy for the synthesis of RGDCySS tetrapeptide. Chem. Res. Chin. Univ. 30, 103–107 (2014). https://doi.org/10.1007/s40242-014-3228-6

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  • DOI: https://doi.org/10.1007/s40242-014-3228-6

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