Fine-Tuning Electroauxiliary-Mediated Peptide Modifications Using Second-Generation Electroactive Amino Acids.

Dhanya Karipal Padinjare Veedu, Luke A Connal, Lara R Malins

Organic letters 2023 May 26

filter terms:

Arylthioether functional groups serve as effective electroauxiliaries for tunable oxidations. Herein, we disclose the synthesis of second-generation glutamine building blocks bearing 2,4-dimethoxythiophenyl and 2,4-dichlorothiophenyl-derived electroauxiliaries. These building blocks improve SPPS efficiency and enable fine-tuning of the electrochemical window for selective anodic oxidation reactions in comparison to first-generation 4-methoxythiophenyl- and 4-nitrothiophenyl-substituted variants. Installation onto a segment of involucrin, a protein component of human skin, emphasizes the practical application of the new building blocks for iterative functionalizations.

Citation

Dhanya Karipal Padinjare Veedu, Luke A Connal, Lara R Malins. Fine-Tuning Electroauxiliary-Mediated Peptide Modifications Using Second-Generation Electroactive Amino Acids. Organic letters. 2023 May 26;25(20):3633-3638