Novel Chemical Strategy for the Synthesis of RGDCySS Tetrapeptide  

作　　者：XU Baofeng YANG Sen ZHU Jinming MA Yudan ZHAO Gang GUO Yi XU Li 

机构地区：[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

出　　处：《Chemical Research in Chinese Universities》2014年第1期103-107,共5页高等学校化学研究（英文版）

基　　金：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 Tech- nology Department of Jilin Province, China（Nos.20106031, 20120967, YYZX2012）.

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-a-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）.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-a-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-a-amino acid anhydride（NCA） 

分 类 号：TQ630.49[化学工程—精细化工] O6-1[理学—化学]