Work

Orthogonal Electrochemical Amine Deprotection: Toward Sustainable Strategies for Peptide Synthesis

Year: 2026

Type: article

Abstract: Deprotection steps employed in peptide synthesis often require harsh conditions and excess reagents, limiting substrate compatibility and sustainability. Electrochemically cleavable protecting groups (e-PGs) offer an attractive alternative. Here, we report the use of 1,3-dithiane-based e-PGs for orthogonal protection of lysine ε-amines in peptide synthesis. Under constant potential electrolysis, deprotection proceeds selectively and orthogonally to other common amino acid protecting groups (Alloc, Boc, Dde, Fmoc, Trt, Pbf, tBu), highlighting potential applications in sustainable peptide synthesis.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c05353

Authors: Esteban Suárez-Picado, Saurabh K. Ahirwar, Lara R. Malins

Institutions: Australian National University, Australian Research Council, ARC Centre of Excellence for Innovations in Peptide and Protein Science

Language: English

Topic: Chemical Synthesis and Analysis

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

Funders: Consellería de Cultura, Educación e Ordenación Universitaria, Xunta de Galicia, Xunta de Galicia, Snow Medical, Australian Research Council

Awards: Backbone Editing Strategies: Underutilised Tools for Peptide Drug Discovery, ARC Centre of Excellence for Innovations in Peptide and Protein Science, G4294722962, G5368869171, G659153159