Visible Light-Mediated Diastereoselective Synthesis of Novel Glycopeptide Mimetics

IF 3.7 2区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Chemistry - A European Journal Pub Date : 2025-02-27 DOI:10.1002/chem.202404457
Jeimy A. C. Vélez, Renan O. Gonçalves, Dr. Pedro H. R. Oliveira, Robert Forster, Stefanie I. Demel, Dr. Julio Z. Schpector, Prof. Dr. Till Opatz, Prof. Dr. Márcio W. Paixão
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Abstract

Herein, we introduce a mild and operationally simple visible-light photochemistry protocol for the synthesis of novel glycopeptide mimetics. This method capitalizes on the reaction between 1,4-dihydropyridine (DHP) containing amino acids and peptides with glycosyl nitrones, showing exceptional stereoselectivity and robust performance across a diverse array of substrates, encompassing both modified glycosides and intricate peptide structures. Furthermore, we underscore the versatility of the resultant compounds through their seamless integration and utility in bioconjugation strategies.

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可见光介导的新型糖肽模拟物的非对映选择性合成。
本文介绍了一种温和且操作简单的可见光光化学方法,用于合成新型糖肽模拟物。该方法利用含有氨基酸和肽的1,4-二氢吡啶(DHP)与糖基硝基之间的反应,在多种底物(包括修饰的糖苷和复杂的肽结构)上表现出优异的立体选择性和稳健的性能。此外,我们强调了合成化合物的多功能性,通过它们在生物偶联策略中的无缝整合和效用。
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来源期刊
Chemistry - A European Journal
Chemistry - A European Journal 化学-化学综合
CiteScore
7.90
自引率
4.70%
发文量
1808
审稿时长
1.8 months
期刊介绍: Chemistry—A European Journal is a truly international journal with top quality contributions (2018 ISI Impact Factor: 5.16). It publishes a wide range of outstanding Reviews, Minireviews, Concepts, Full Papers, and Communications from all areas of chemistry and related fields. Based in Europe Chemistry—A European Journal provides an excellent platform for increasing the visibility of European chemistry as well as for featuring the best research from authors from around the world. All manuscripts are peer-reviewed, and electronic processing ensures accurate reproduction of text and data, plus short publication times. The Concepts section provides nonspecialist readers with a useful conceptual guide to unfamiliar areas and experts with new angles on familiar problems. Chemistry—A European Journal is published on behalf of ChemPubSoc Europe, a group of 16 national chemical societies from within Europe, and supported by the Asian Chemical Editorial Societies. The ChemPubSoc Europe family comprises: Angewandte Chemie, Chemistry—A European Journal, European Journal of Organic Chemistry, European Journal of Inorganic Chemistry, ChemPhysChem, ChemBioChem, ChemMedChem, ChemCatChem, ChemSusChem, ChemPlusChem, ChemElectroChem, and ChemistryOpen.
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