Stereoselective synthesis of a phosphonate pThr mimetic via palladium-catalyzed γ-C(sp3)-H activation for peptide preparation.
Org Biomol Chem
; 17(8): 2099-2102, 2019 02 20.
Article
in En
| MEDLINE
| ID: mdl-30714601
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.
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MEDLINE
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En
Year:
2019
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Article