Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 17, Issue 8, Pages 2099-2102Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8ob02999g
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Funding
- National Key R&D Program of China [2018YFA0507600]
- National Natural Science Foundation of China [21672125, 91753122]
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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 gamma-methyl C(sp(3))-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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