Organic Letters 2003-09-04

Building functionalized peptidomimetics: new electroauxiliaries and the use of a chemical oxidant for introducing N-acyliminium ions into peptides.

Haizhou Sun, Kevin D Moeller

Index: Org. Lett. 5(18) , 3189-92, (2003)

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Abstract

[reaction: see text] 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.