title: Alpha-trialkylsilyl amino acid stability.
abstract: Alpha-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. [structure: see text]
authors.affiliation: Department of Chemistry, Temple University, Philadelphia, PA 19010, USA.
authors.forename: Guodong
authors.initials: G
authors.lastname: Liu
authors.forename: Scott McN
authors.initials: SM
authors.lastname: Sieburth
mesh_terms: D000478:Alkylation; D000596:Amino Acids / Q000737:chemistry*; D004355:Drug Stability; D008697:Methane; D008958:Models, Molecular; D012821:Silanes; D012825:Silicon
chemical_list: D000596:Amino Acids; D012821:Silanes; D008697:Methane; D012825:Silicon