Light-Driven Site-Selective Glycosylation of Native Carbohydrates

João A. Pacheco, Nuno R. Candeias

Research output: Contribution to journalArticleScientificpeer-review

Abstract

Carbohydrates constitute the largest source of biomass on Earth, but their synthetic modification is challenging due to their high content in oxygen functionalities. The site- and stereoselective modification of native sugars is a definite goal of glycochemistry research. Recent efforts to bypass the need for protecting groups, leveraging selective activation through photochemical mechanisms for site-selective C−C bond formation from native sugars, are likely to largely impact all glycochemistry-related areas. Davis, Koh, and co-workers have recently presented their use of photocatalysis to develop a “cap and glycosylate” approach for the site- and stereoselective C-glycosylation of native sugars. A modernized direct radical functionalization of in situ formed thioglycoside using photocatalysis was used in the synthetic manipulation of unprotected carbohydrates. This allowed reaching complex saccharides, and post-translational modification of proteins.

Original languageEnglish
Article numbere202414424
JournalAngewandte Chemie - International Edition
Volume63
Issue number50
DOIs
Publication statusPublished - 9 Dec 2024
Publication typeA1 Journal article-refereed

Funding

We thank Funda\u00E7\u00E3o para a Ci\u00EAncia e Tecnologia e Minist\u00E9rio da Ci\u00EAncia, Tecnologia e Ensino Superior (FCT/MCTES) for the financial support through national funds within the scope of funding LA/P/0008/2020, UIDB/50006/2020, UIDP/50006/2020, PTDC/QUI-QOR/1131/2020. NC thanks FCT for the grant on scientific employment stimulus (institutional call, reference CEECINST/00026/2018). JP thanks FCT for his PhD grant UI/BD/153616/2022. We thank Funda\u00E7\u00E3o para a Ci\u00EAncia e Tecnologia e Minist\u00E9rio da Ci\u00EAncia, Tecnologia e Ensino Superior (FCT/MCTES) for the financial support through national funds within the scope of funding LA/P/0008/2020, UIDB/50006/2020, UIDP/50006/2020, PTDC/QUI\u2010QOR/1131/2020. NC thanks FCT for the grant on scientific employment stimulus (institutional call, reference CEECINST/00026/2018). JP thanks FCT for his PhD grant UI/BD/153616/2022.

FundersFunder number
Fundação para a Ciência e a Tecnologia
Fundação para a Ciência e Tecnologia e Ministério da Ciência, Tecnologia e Ensino Superior
MCTESLA/P/0008/2020, UIDP/50006/2020, CEECINST/00026/2018, UIDB/50006/2020, PTDC/QUI-QOR/1131/2020, UI/BD/153616/2022

    Keywords

    • Carbohydrates
    • Photocatalysis
    • Radicals
    • Renewable resources
    • Sustainable Chemistry

    Publication forum classification

    • Publication forum level 3

    ASJC Scopus subject areas

    • Catalysis
    • General Chemistry

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