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

Abstract

We report a facile synthetic strategy toward CH2-substituted phosphothreonine mimetic. Herein, inexpensive valine with directing group was converted into homothreonine via palladium-catalyzed γ-methyl C(sp3)-H bond activation, followed by construction of phosphorus-carbon bond via 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 chances to prepare not only phosphopeptides but also phosphoproteins resistant to phosphatases.

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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, Accepted Manuscript
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    Stereoselective synthesis of phosphonate pThr mimetic via palladium-catalyzed γ-C(sp3)-H activation for peptide assembling

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

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