Building functionalized peptidomimetics: Use of electroauxiliaries for introducing N-acyliminium ions into peptides

Haizhou Sun, Connor Martin, David Kesselring, Rebecca Keller, Kevin D. Moeller

Research output: Contribution to journalArticlepeer-review

75 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)13761-13771
Number of pages11
JournalJournal of the American Chemical Society
Volume128
Issue number42
DOIs
StatePublished - Oct 25 2006

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