α-Trialkylsilyl Amino Acid Stability

α-Trialkylsilyl amino acids have been evaluated for their stability toward methanolysis as a model for physiological conditions. The juxtaposition of amine and carbonyl groups significantly destabilizes the silicon−carbon bond, but changing a single methyl on silicon to an ethyl led to a dramatic stability enhancement. Converting the ester to an amide gave an additional jump in stability, suggesting broad potential for these novel amino acids in bioactive peptides and pharmaceuticals.

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