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

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.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-03-04
DOI
https://doi.org/10.1021/acs.joc.5c00030
Citations
3
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
2.37

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article

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

Márcio W. Paixão, Emanuele F. Pissinati, Till Opatz, Lívia M. S. Barreto
3 citations
The Journal of Organic Chemistry
Fluorine in Organic Chemistry
2.37
article

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

Márcio W. Paixão, Emanuele F. Pissinati, Till Opatz, Lívia M. S. Barreto
article en
3 citations

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.

The Journal of Organic ChemistryVol. 90(10)
Universidade Federal de São Carlos (BR), Johannes Gutenberg University Mainz (DE), Laboratoire de Synthèse Organique (FR)
Fundação de Amparo à Pesquisa do Estado de São Paulo, Coordenação de Aperfeiçoamento de Pessoal de Nível Superior, Conselho Nacional de Desenvolvimento Científico e Tecnológico
Clean water and sanitation
Openalex Percentile: Top 13%
Fluorine in Organic Chemistry
2.37
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