Synthesis of O‐Acyl Isopeptides |
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Authors: | Youhei Sohma Yoshiaki Kiso |
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Institution: | 1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, , Bunkyo‐ku, Tokyo, 113‐0033 Japan;2. Kanai Life Science Catalysis Project, ERATO, Japan Science and Technology Agency (JST), , Kawaguchi‐shi, Saitama, 332‐0012 Japan;3. Laboratory of Peptide Science, Nagahama Institute of Bio‐Science and Technology, , Nagahama, Shiga, 526‐0829 Japan |
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Abstract: | O‐Acyl isopeptides, in which the N‐acyl linkage on the hydroxyamino acid residue (e.g., Ser and Thr) is replaced with an O‐acyl linkage, generally possess superior water‐solubility to their corresponding native peptides, as well as other distinct physicochemical properties. In addition, O‐acyl isopeptides can be rapidly converted into their corresponding native peptide under neutral aqueous conditions through an O‐to‐N acyl migration. By exploiting these characteristics, researchers have applied the O‐acyl isopeptide method to various peptide‐synthesis fields, such as the synthesis of aggregative peptides and convergent peptide synthesis. This O‐acyl‐isopeptide approach also serves as a means to control the biological function of the peptide in question. Herein, we report the synthesis of O‐acyl isopeptides and some of their applications. |
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Keywords: | acyl migration amyloids isopeptides ligation peptides |
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