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Author Spotlight: In Silico Creation and Impact of Carbonylated Amino Acids on Protein Structure and Function
Published on: April 26, 2024
Fine-Tuning Electroauxiliary-Mediated Peptide Modifications Using Second-Generation Electroactive Amino Acids
Dhanya Karipal Padinjare Veedu1,2, Luke A Connal1, Lara R Malins1,2
1Research School of Chemistry, Australian National University, Canberra, ACT 2601, Australia.
Abstract:
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.
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