Building functionalized peptidomimetics: use of electroauxiliaries for introducing N-acyliminium ions into peptides.
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.
Sun
Haizhou
H
Department of Chemistry, Washington University, St. Louis, Missouri 63130, USA.
Martin
Connor
C
Kesselring
David
D
Keller
Rebecca
R
Moeller
Kevin D
KD
D000215:Acylation; D000596:Amino Acids / Q000737:chemistry*; D004151:Dipeptides / Q000737:chemistry; D004572:Electrolysis; D007097:Imines / Q000737:chemistry*; D007477:Ions; D008956:Models, Chemical; D018716:Molecular Mimicry; D017646:Organosilicon Compounds / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D010455:Peptides / Q000138:chemical synthesis*; D012825:Silicon / Q000737:chemistry*
D000596:Amino Acids; D004151:Dipeptides; D007097:Imines; D007477:Ions; D017646:Organosilicon Compounds; D010455:Peptides; D012825:Silicon