Late-stage modification pathways are undeniably valuable for the incorporation of diverse functionalities into peptide sequences.1 General modification strategies, including bioconjugation, ligation, macrocyclization, and stapling techniques, have enabled the construction of peptide-based natural products, as well as diverse structural analogues, that are implicated in important biochemical processes and serve as promising therapeutic leads.2 Despite the general appeal of electro-organic synthesis,3 electrochemistry is scarcely employed as a modification approach for peptides. Nonetheless, electro-organic methods, especially oxidation reactions, are highly desirable approaches owing to the ability to avoid toxic reagents, to minimize step count, and importantly to tune conditions by varying the oxidation potential. Reported methods which leverage the reactivity of compounds bearing amide and carbamate functionalities—relevant motifs for the modification of peptide substrates—include the anodic oxidation of proline derivatives reported by Kim et al.4 and the anodic functionalization of polylactams, demonstrated by Aubé, Moeller and coworkers.5 Building off of these technologies, herein we disclose the development of an electro-auxiliary based anodic oxidation strategy for the functionalization of amino acid derivatives and peptide model systems with diverse nucleophiles