Synthesis of (Z)-alkene-containing cis-proline dipeptide mimetics using samarium(II) diiodide (SmI2)-mediated reductive alkylation reaction |
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Authors: | Yoshikazu Sasaki Akira Shigenaga Akira Otaka |
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Affiliation: | a Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan b Graduate School of Pharmaceutical Sciences, The University of Tokushima, Tokushima 770-8505, Japan |
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Abstract: | The amide bond between an amino acid and proline can take the trans- or cis-conformation. The conformation influences both the structure and function of peptides and proteins. Therefore, constrained mimetic, which corresponds to Pro-dipeptides whose amide bond is replaced with an (E)- or (Z)-alkene, is a useful bioprobe for elucidating the structure-function relationship of peptides and proteins. Herein, we report the synthesis of cis-(Z)-alkene-containing Pro-dipeptide mimetics via a samarium(II) diiodide (SmI2)-mediated reductive alkylation reaction. |
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Keywords: | Samarium diiodide Reductive alkylation reaction Dipeptide mimetic Proline |
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