Photocatalytic Synthesis of Difluorinated Glycoamino Acids and Neoglycopeptides via Hydrodifluoroacetamidation of Vinyl-C-glycosides

Author(s)

Pissinati, Emanuele F. ; Barreto, Livia M. S. ; Opatz, Till ; Paixao, Maarcio W.

• Document type: Journal article
• Source: Journal of Organic Chemistry; v. 90, n. 10, p. 6-pg., 2025-03-04.

Abstract

A photocatalytic approach for the synthesis of difluorinated glycoamino acids and neoglycopeptides from bromodifluoroacetamides and sugar-derived olefins is presented. This method stands out because of its simplicity, atomic economy, and mild reaction conditions, allowing compatibility with both natural and unnatural amino acids and peptides. Additionally, it demonstrates efficacy across a variety of carbohydrates, including furanoses, pyranoses, pentose, hexoses, and disaccharides, accommodating an extensive range of protecting groups, even in their deprotected forms. (AU)

• FAPESP's process: 22/04597-0 - Synthesis of non-proteinogenic amino acids and modification of peptides using photocatalysis
• Grantee: Emanuele Ferrari Pissinati
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 21/06099-5 - Development of new photochemical methodologies for the synthesis of small molecule and biomolecule modifications
• Grantee: Márcio Weber Paixão
• Support Opportunities: Regular Research Grants
• FAPESP's process: 23/12718-5 - Bromodifluoroacetic acid derivatives as linkers for the synthesis of hybrid biomolecules using photoredox catalysis
• Grantee: Emanuele Ferrari Pissinati
• Support Opportunities: Scholarships abroad - Research Internship - Doctorate