August 15, 2003

Building Functionalized Peptidomimetics: New Electroauxiliaries and the Use of a Chemical Oxidant for Introducing N-Acyliminium Ions into Peptides

Haizhou Sun and Kevin D. Moeller
Org. Lett., 2003, 5 (18), pp 3189–3192

The removal of electroauxiliaries from peptide substrates with chemical oxidants has been examined as a method for inserting N-acyliminium ions into the peptides. To this end, it was found that both 4-methoxyphenyldimethylsilyl and 2,4-dimethoxyphenyldimethylsilyl electroauxiliaries were readily cleaved with the use of ceric ammonium nitrate. Of the two groups, the 2,4-dimethoxyphenyldimethylsilyl electroauxiliary was the most labile under the oxidative conditions. The oxidation reactions were shown to be compatible with the use of a solid-phase substrate.