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

Emanuele F Pissinati, Lívia M S Barreto, Till Opatz, Márcio W Paixão

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Article in The Journal of organic chemistry, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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4 authors.

Emanuele F PissinatiLaboratory for Sustainable Organic Synthesis and Catalysis, Department of Chemistry, Federal University of São Carlos-UFSCar, 13565-905 São Carlos, São Paulo, Brazil.ORCID 0000-0002-5892-8528

Lívia M S BarretoLaboratory for Sustainable Organic Synthesis and Catalysis, Department of Chemistry, Federal University of São Carlos-UFSCar, 13565-905 São Carlos, São Paulo, Brazil.

Till OpatzDepartment of Chemistry, Johannes Gutenberg-University, Duesbergweg 10-14, 55128 Mainz, Germany.ORCID 0000-0002-3266-4050

Márcio W PaixãoLaboratory for Sustainable Organic Synthesis and Catalysis, Department of Chemistry, Federal University of São Carlos-UFSCar, 13565-905 São Carlos, São Paulo, Brazil.ORCID 0000-0002-0421-2831

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

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.

Identifiers

PMID40035229

DOI10.1021/acs.joc.5c00030

PMCPMC11915378

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