916049-43-9Relevant articles and documents
Building functionalized peptidomimetics: Use of electroauxiliaries for introducing N-acyliminium ions into peptides
Sun, Haizhou,Martin, Connor,Kesselring, David,Keller, Rebecca,Moeller, Kevin D.
, p. 13761 - 13771 (2007/10/03)
A series of silyl-substituted amino acids have been synthesized, inserted into peptides, and then employed as precursors for oxidatively generating reactive N-acyliminium ions. Both electrochemical and chemical oxidation procedures have been employed. N-Acyliminium ion generation in a solid-phase substrate as well as application to a small library of functionalized dipeptides has been demonstrated. Limitations in terms of how electron-rich the silyl groups can be as well as the compatibility of multiple silyl groups within a longer peptide are defined.