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通过乙烯基-C-糖苷的氢二氟乙酰化光催化合成二氟糖基氨基酸和新糖肽。

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

作者信息

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

机构信息

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

Department of Chemistry, Johannes Gutenberg-University, Duesbergweg 10-14, 55128 Mainz, Germany.

出版信息

J Org Chem. 2025 Mar 14;90(10):3733-3738. doi: 10.1021/acs.joc.5c00030. Epub 2025 Mar 4.

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.

摘要

本文介绍了一种通过光催化方法,从溴二氟乙酰胺和糖衍生的烯烃合成二氟代糖氨基酸和新糖肽的方法。该方法因其操作简单、原子经济性高以及反应条件温和而脱颖而出,能够与天然和非天然氨基酸及肽兼容。此外,它对多种碳水化合物都有效,包括呋喃糖、吡喃糖、戊糖、己糖和二糖,即使在其去保护形式下也能适应广泛的保护基团。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c5f7/11915378/ee2325b62109/jo5c00030_0002.jpg

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