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Synthesis and secondary conformations of homochiral β-oligopeptides containing aryl side chains

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Abstract

A series of novel homochiral α-oligopeptides bearing aryl side chains was designed and synthesized from (S)-α-phenyl-α-amino acid derivatives by solution-phase methods. By means of circular dichroism(CD), Fouriertransform infrared spectrometry(FTIR), powder X-ray diffraction analysis(XRD) and density functional theory(DFT) calculations, we suggest that dipeptide P-2 and tripeptide P-3 adopt random coil-like conformations, pentapeptide P-5 and hexapeptide P-6 adopt stable 12-helix conformations in both solution and solid-state. Meanwhile, tetrapeptide P-4 adopt random coil-like conformation in solution and adopt 12-helix conformation in solid state.

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Authors and Affiliations

  1. Key Laboratory for Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, P. R. China

    Yonghong Zhang, Weicheng Yuan & Xiaomei Zhang

  2. University of Chinese Academy of Sciences, Beijing, 100049, P. R. China

    Yonghong Zhang

  3. School of Life Science and Engineering, Southwest University of Science and Technology, Mianyang, 621010, P. R. China

    Liangchun Li

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  1. Yonghong Zhang
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  2. Liangchun Li
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  3. Weicheng Yuan
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  4. Xiaomei Zhang
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Correspondence to Xiaomei Zhang.

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Supported by the National Natural Science Foundation of China(No.21172217).

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Zhang, Y., Li, L., Yuan, W. et al. Synthesis and secondary conformations of homochiral β-oligopeptides containing aryl side chains. Chem. Res. Chin. Univ. 31, 381–387 (2015). https://doi.org/10.1007/s40242-015-4423-9

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  • DOI: https://doi.org/10.1007/s40242-015-4423-9

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