Building functionalized peptidomimetics: new electroauxiliaries and the use of a chemical oxidant for introducing N-acyliminium ions into peptides.
[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.
Sun
Haizhou
H
Department of Chemistry, Washington University, St. Louis, Missouri 63130, USA.
Moeller
Kevin D
KD
D000215:Acylation; D002563:Cerium / Q000737:chemistry; D004563:Electrochemistry; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry; D016877:Oxidants / Q000737:chemistry*; D010084:Oxidation-Reduction; D010452:Peptide Biosynthesis; D010455:Peptides / Q000737:chemistry*
D007097:Imines; D017646:Organosilicon Compounds; D016877:Oxidants; D010455:Peptides; D002563:Cerium; C004653:ceric ammonium nitrate