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Issue 8, 2019
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Stereoselective synthesis of a phosphonate pThr mimetic via palladium-catalyzed γ-C(sp3)–H activation for peptide preparation

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Abstract

We report a facile synthetic strategy toward CH2-substituted phosphothreonine mimetics. Herein, inexpensive valine with a directing group was converted into homothreonine via palladium-catalyzed γ-methyl C(sp3)–H bond activation, followed by construction of a phosphorus–carbon bond via the well-developed Appel reaction and Michaelis–Becker reaction with a total yield of 30%. Furthermore, the derived mimetic was applied for solid-phase synthesis of two phosphopeptide inhibitors. This efficient synthesis provides a chance to prepare not only phosphopeptides but also phosphoproteins resistant to phosphatases.

Graphical abstract: Stereoselective synthesis of a phosphonate pThr mimetic via palladium-catalyzed γ-C(sp3)–H activation for peptide preparation

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Publication details

The article was received on 02 Dec 2018, accepted on 08 Jan 2019 and first published on 08 Jan 2019


Article type: Communication
DOI: 10.1039/C8OB02999G
Citation: Org. Biomol. Chem., 2019,17, 2099-2102

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    Stereoselective synthesis of a phosphonate pThr mimetic via palladium-catalyzed γ-C(sp3)–H activation for peptide preparation

    H. Duan, H. Chen, Q. Yu, J. Hu, Y. Li and Y. Chen, Org. Biomol. Chem., 2019, 17, 2099
    DOI: 10.1039/C8OB02999G

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