Novel Chemical Strategy for the Synthesis of RGDCySS Tetrapeptide

doi:10.1007/s40242-014-3228-6

Chemical Research in Chinese Universities ›› 2014, Vol. 30 ›› Issue (1): 103-107.doi: 10.1007/s40242-014-3228-6

• Articles • Previous Articles Next Articles

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).

Abstract

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).

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]. Chemical Research in Chinese Universities, 2014, 30(1): 103-107.

References

[1] Sillerud L. O., Larson R. S., Curr. Protein Pept. Sci., 2005, 6, 151

[2] Guo W. J., Giancotti F. G., Nat. Rev. Mol. Cell Bio., 2004, 5, 816

[3] Smith A. E., Helenius A., Science, 2004, 304, 237

[4] Gabriel M., van Nieuw Amerongen G. P., van Hinsbergh V. W. M., van Nieuw Amerongen A. V., Zentner A., J. Biomater. Sci. Polymer Edn., 2006, 17, 567

[5] Yang R. S., Tang C. H., Chuang W. J., Huang T. H., Peng H. C., Huang T. F., Fu W. M., Toxicon, 2005, 45, 661

[6] Anselme K., Biomaterials, 2000, 21, 667

[7] Mastrobattista E., van der Aa M. A. E. M., Hennink W. E., Crommelin D. J. A., Nat. Rev. Drug Discov., 2006, 5, 115

[8] You M. L., Peng G. F., Li J. A., Ma P., Wang Z. H., Shu W. L., Peng S. W., Chen G. Q., Biomaterials, 2011, 32, 2305

[9] Zhang X. Z., Chen X. Y., Appl. Radiat. Isotopes, 2007, 65, 708

[10] Chan W. C. W., Nie S. M., Science, 1998, 281, 2016

[11] Kambe Y., Yamamoto K., Kojima K., Tamada Y., Tomita N., Biomaterials, 2010, 31, 7503

[12] Shi L. F., Rosenzweig N., Rosenzweig Z., Anal. Chem., 2007, 79, 208

[13] Wu X. Y., Liu H. J., Liu J. Q., Haley K. N., Treadway J. A., Larson J. P., Ge N. F., Peale F., Bruchez M. P., Nat. Biotechnol., 2003, 21, 41

[14] Du H. R., Cui C. Y., Wang L. L., Liu H., Cui G. H., Mol. Pharmaceut., 2011, 8, 1224

[15] Anderson G. W., Zimmerman J. E., Callahan F. M., J. Am. Chem. Soc., 1967, 89, 5012

[16] Kaiser E. T., Mihara H., Laforet G. A., Kelly J. W., Walters L., Findeis M. A., Sasak T., Science, 1989, 243, 187

[17] Stoev S., Cheng L. L., Manning M., Wo N. C., Szeto H. H., J. Pept. Sci., 2006, 12, 592

[18] Cen T., Zhou C., Wu X. M., Jiang B., Zhu S. M., Shen S. B., Chinese J. Org. Chem., 2010, 30, 837

[19] Gyanda R., Banerjee J., Chang Y. P., Phillips A. M., Toll L., Armishaw C. J., J. Pept. Sci., 2013, 19, 16

[20] Mollica A., Feliciani F., Stefanucci A., Fadeev E. A., Pinnen F., Protein Pept. Lett., 2012, 19, 1245

[21] Lalithamba H. S., Hemantha H. P., Sureshbabu V. V., Protein Pept. Lett., 2011, 18, 848

[22] Wei Y., Ji Y., Ji J., Chem. J. Chinese Universities, 2012, 33(1), 193

[23] Zheng Y., Wu G., Zhu X. R., Li Y. J., Ma Y. H., Zhao X., Lu T., Zhu Y. Q., Chem. Res. Chinese Universities, 2011, 27(2), 224

[24] Huang Y. B., Xiao Y. P., Wang H., Hou R. Z., Zhang N., Wu X. X., Xu L., Zhang X. Z., J. Biotechnol., 2005, 116, 51

[25] Bacheva A. V., Belyaeva A. V., Lysogorskaya E. N., Oksenoit E. S., Lozinsky V. I., Filippova I. Y., J. Mol. Catal. B Enzym., 2005, 32, 253

[26] Kaki S. S., Grey C., Adlercreutz P., J. Biotechnol., 2012, 157, 344

[27] Hou R. Z., Liu Y. J., Zhang N., Huang Y. B., Wang H., Yang Y., Xu L., Zhang X. Z., Prep. Biochem. Biotech., 2006, 36, 243

[28] Wang H., Zhao M. F., Ma C. Y., Jing W., Huang Y. B., Hou R. Z., Zeng H. B., Xu L., Zhang X. Z., Chem. Res. Chinese Universities, 2006, 22(5), 612

[29] Zhang X. Z., Hou R. Z., Xu L., Huang Y. B. ; Eds. Whittall J., Sutton P., Practical Methods for Biocatalysis and Biotransformations, John Wiley & Sons Ltd., Chichester, 2010, 165

[30] Huang Y. B., Cai Y., Yang S., Wang H., Hou R. Z., Xu L., Wu X. X., Zhang X. Z., J. Biotechnol., 2006, 125, 311

Novel Chemical Strategy for the Synthesis of RGDCySS Tetrapeptide

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 6

Recommended Articles

Metrics

Comments

[1]	WU Fanghui, XU Fan, CHEN Le, JIANG Binbin, SUN Wenbin, WEI Xianwen. Cuprous Oxide/Nitrogen-doped Graphene Nanocomposites as Electrochemical Sensors for Ofloxacin Determination [J]. Chemical Research in Chinese Universities, 2016, 32(3): 468-473.
[2]	FENG Jing, HOU Xiangyu, CHEN Tingting, LIU Shengna, FAN Zhuangjun, REN Yueming, LÜ Yanzhuo. Synthesis of NiFe₂O₄ Nanowires with NiO Nanosheet as Precursor via a Topochemical Solid State Method [J]. Chemical Research in Chinese Universities, 2015, 31(5): 885-889.
[3]	LIU Chunyu, WANG Shaoyan, FU Cuicui, LI Haibo, XU Shuping, XU Weiqing. Preparation of Surface-enhanced Raman Scattering(SERS)-active Optical Fiber Sensor by Laser-induced Ag Deposition and Its Application in Bioidentification of Biotin/Avidin [J]. Chemical Research in Chinese Universities, 2015, 31(1): 25-30.
[4]	GUO Yi, ZHANG Yong-xia, JIANG Xin, ZHANG Xue-zhong, WU Yi* and XU Li*. Chemo-enzymatic Synthesis of Z-Asp-Val-Tyr-NH2―A Precursor Tripeptide of Thymopentin [J]. Chemical Research in Chinese Universities, 2010, 26(6): 942-947.
[5]	HOU Rui-zhen , LI Hong-mei , LIU Yun-jia , ZHANG Long , XU Li , ZHANG Xue-zhong . Protease-catalyzed Synthesis of Bz-Arg-Gly-Asp-OMein Full Aqueous Medium [J]. Chemical Research in Chinese Universities, 2007, 23(6): 693-696.
[6]	ZOU Ming-zhu, SHENG Gui-hua, ZHENG Guo-dong, ZHFNG Yan-sheng . Studies on the Gold-Coated Electrode with Grid [J]. Chemical Research in Chinese Universities, 1992, 8(4): 461-464.