Citation: Jian Chen, Bei Zhang, Cao Xie, Yi Lu, Wei Wu. Synthesis of a highly hydrophobic cyclic decapeptide by solid-phase synthesis of linear peptide and cyclization in solution[J]. Chinese Chemical Letters, ;2010, 21(4): 391-394. doi: 10.1016/j.cclet.2009.11.026 shu

Synthesis of a highly hydrophobic cyclic decapeptide by solid-phase synthesis of linear peptide and cyclization in solution

School of Pharmacy, Fudan University, Shanghai 201203, China

Received Date: 17 August 2009

Fund Project: We would like to thank Dr. Wuyuan Lu, Institute of Human Virology, University of Maryland School of Medicine for his support of this effort and Zengyi Dai for her help with synthesis. This work was supported by National Natural Science Foundation (No. 30672546), Shanghai Municipal Committee of S & T (No. 0652nm013) and National Key Basic Research Program of China (No. 2007CB935800).

A general method was described to synthesize a highly hydrophobic cyclic peptide,cyclo[(L)W(L)W(L)W(L)W(L)Q]where underlines indicate D-configuration of the amino acid,by a two-step solid-phase/solution synthesis strategy.The linear decapeptide was assembled by standard Boc chemistry on solid-phase and subsequently cyclized in solution with high efficiency and reproducibility.In subsequent purification by semi-preparative HPLC,50%(v/v)DMF/H₂O was employed as the solvent to overcome the difficulty of solubilization for the hydrophobic cyclic decapeptide and achieved a total yield of 30-35% with a purity of over 98%.
- Cyclic peptide,
- Decapeptide,
- cyclo[(L)W(L)W(L)W(L)W(L)Q],
- Solid-phase synthesis,
- Cyclization,
- Purification
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