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Photosensitizer-free visible-light-promoted glycosylation enabled by 2-glycosyloxy tropone donors

Photochemical glycosylation has attracted considerable attention in carbohydrate chemistry. However, to the best of our knowledge, visible-light-promoted glycosylation via photoactive glycosyl donor has not been reported. In the study, we report a photosensitizer-free visible-light-mediated glycosyl...

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Autores principales: Zhang, Jing, Luo, Zhao-Xiang, Wu, Xia, Gao, Chen-Fei, Wang, Peng-Yu, Chai, Jin-Ze, Liu, Miao, Ye, Xin-Shan, Xiong, De-Cai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10695961/
https://www.ncbi.nlm.nih.gov/pubmed/38049421
http://dx.doi.org/10.1038/s41467-023-43786-y
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author Zhang, Jing
Luo, Zhao-Xiang
Wu, Xia
Gao, Chen-Fei
Wang, Peng-Yu
Chai, Jin-Ze
Liu, Miao
Ye, Xin-Shan
Xiong, De-Cai
author_facet Zhang, Jing
Luo, Zhao-Xiang
Wu, Xia
Gao, Chen-Fei
Wang, Peng-Yu
Chai, Jin-Ze
Liu, Miao
Ye, Xin-Shan
Xiong, De-Cai
author_sort Zhang, Jing
collection PubMed
description Photochemical glycosylation has attracted considerable attention in carbohydrate chemistry. However, to the best of our knowledge, visible-light-promoted glycosylation via photoactive glycosyl donor has not been reported. In the study, we report a photosensitizer-free visible-light-mediated glycosylation approach using a photoactive 2-glycosyloxy tropone as the donor. This glycosylation reaction proceeds at ambient temperature to give a wide range of O-glycosides or oligosaccharides with yields up to 99%. This method is further applied in the stereoselective preparation of various functional glycosyl phosphates/phosphosaccharides, the construction of N-glycosides/nucleosides, and the late-stage glycosylation of natural products or pharmaceuticals on gram scales, and the iterative synthesis of hexasaccharide. The protocol features uncomplicated conditions, operational simplicity, wide substrate scope (58 examples), excellent compatibility with functional groups, scalability of products (7 examples), and high yields. It provides an efficient glycosylation method for accessing O/N-glycosides and glycans.
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spelling pubmed-106959612023-12-06 Photosensitizer-free visible-light-promoted glycosylation enabled by 2-glycosyloxy tropone donors Zhang, Jing Luo, Zhao-Xiang Wu, Xia Gao, Chen-Fei Wang, Peng-Yu Chai, Jin-Ze Liu, Miao Ye, Xin-Shan Xiong, De-Cai Nat Commun Article Photochemical glycosylation has attracted considerable attention in carbohydrate chemistry. However, to the best of our knowledge, visible-light-promoted glycosylation via photoactive glycosyl donor has not been reported. In the study, we report a photosensitizer-free visible-light-mediated glycosylation approach using a photoactive 2-glycosyloxy tropone as the donor. This glycosylation reaction proceeds at ambient temperature to give a wide range of O-glycosides or oligosaccharides with yields up to 99%. This method is further applied in the stereoselective preparation of various functional glycosyl phosphates/phosphosaccharides, the construction of N-glycosides/nucleosides, and the late-stage glycosylation of natural products or pharmaceuticals on gram scales, and the iterative synthesis of hexasaccharide. The protocol features uncomplicated conditions, operational simplicity, wide substrate scope (58 examples), excellent compatibility with functional groups, scalability of products (7 examples), and high yields. It provides an efficient glycosylation method for accessing O/N-glycosides and glycans. Nature Publishing Group UK 2023-12-04 /pmc/articles/PMC10695961/ /pubmed/38049421 http://dx.doi.org/10.1038/s41467-023-43786-y Text en © The Author(s) 2023 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Zhang, Jing
Luo, Zhao-Xiang
Wu, Xia
Gao, Chen-Fei
Wang, Peng-Yu
Chai, Jin-Ze
Liu, Miao
Ye, Xin-Shan
Xiong, De-Cai
Photosensitizer-free visible-light-promoted glycosylation enabled by 2-glycosyloxy tropone donors
title Photosensitizer-free visible-light-promoted glycosylation enabled by 2-glycosyloxy tropone donors
title_full Photosensitizer-free visible-light-promoted glycosylation enabled by 2-glycosyloxy tropone donors
title_fullStr Photosensitizer-free visible-light-promoted glycosylation enabled by 2-glycosyloxy tropone donors
title_full_unstemmed Photosensitizer-free visible-light-promoted glycosylation enabled by 2-glycosyloxy tropone donors
title_short Photosensitizer-free visible-light-promoted glycosylation enabled by 2-glycosyloxy tropone donors
title_sort photosensitizer-free visible-light-promoted glycosylation enabled by 2-glycosyloxy tropone donors
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10695961/
https://www.ncbi.nlm.nih.gov/pubmed/38049421
http://dx.doi.org/10.1038/s41467-023-43786-y
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