Direct radical functionalization of native sugars

Jiang, Yi1,2,3; Wei, Yi1; Zhou, Qian-Yi1; Sun, Guo-Quan1; Fu, Xia-Ping2,3; Levin, Nikita2,3; Zhang, Yijun1,4; Liu, Wen-Qiang1; Song, Ningxi1; Mohammed, Shabaz2,5,6; Davis, Benjamin G.2,3,5; Koh, Ming Joo1

2024-06-01

10.1038/s41586-024-07548-0

NATURE   影响因子和分区

0028-0836

1476-4687

["Naturally occurring (native) sugars and carbohydrates contain numerous hydroxyl groups of similar reactivity 1,2 . Chemists, therefore, rely typically on laborious, multi-step protecting-group strategies 3 to convert these renewable feedstocks into reagents (glycosyl donors) to make glycans. The direct transformation of native sugars to complex saccharides remains a notable challenge. Here we describe a photoinduced approach to achieve site- and stereoselective chemical glycosylation from widely available native sugar building blocks, which through homolytic (one-electron) chemistry bypasses unnecessary hydroxyl group masking and manipulation. This process is reminiscent of nature in its regiocontrolled generation of a transient glycosyl donor, followed by radical-based cross-coupling with electrophiles on activation with light. Through selective anomeric functionalization of mono- and oligosaccharides, this protecting-group-free 'cap and glycosylate' approach offers straightforward access to a wide array of metabolically robust glycosyl compounds. Owing to its biocompatibility, the method was extended to the direct post-translational glycosylation of proteins.","A radical-based method for functionalizing native sugars shows a way to remove typical protecting-group manipulations."]

SCI

英语

其他

Ministry of Education of Singapore[A-8000941-00-00] ; Engineering and Physical Sciences Research Council[V011359/1]

Science & Technology - Other Topics

Multidisciplinary Sciences

WOS:001262428800014

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BIOLOGY & BIOCHEMISTRY ; CLINICAL MEDICINE ; MULTIDISCIPLINARY ; PLANT & ANIMAL SCIENCE ; ENVIRONMENT/ECOLOGY ; SOCIAL SCIENCES, GENERAL ; MICROBIOLOGY ; ECONOMICS BUSINESS ; IMMUNOLOGY ; MATERIALS SCIENCE ; COMPUTER SCIENCE ; SPACE SCIENCE ; MOLECULAR BIOLOGY & GENETICS ; CHEMISTRY ; NEUROSCIENCE & BEHAVIOR ; PHYSICS ; GEOSCIENCES ; ENGINEERING

Web of Science

1.Natl Univ Singapore, Dept Chem, Singapore, Singapore
2.Rosalind Franklin Inst, Harwell Sci & Innovat Campus, Didcot, England
3.Univ Oxford, Dept Pharmacol, Oxford, England
4.Southern Univ Sci & Technol, Dept Chem, Shenzhen, Peoples R China
5.Univ Oxford, Dept Chem, Oxford, England
6.Univ Oxford, Dept Biochem, Oxford, England

Jiang, Yi,Wei, Yi,Zhou, Qian-Yi,et al. Direct radical functionalization of native sugars[J]. NATURE,2024.

Jiang, Yi.,Wei, Yi.,Zhou, Qian-Yi.,Sun, Guo-Quan.,Fu, Xia-Ping.,...&Koh, Ming Joo.(2024).Direct radical functionalization of native sugars.NATURE.

Jiang, Yi,et al."Direct radical functionalization of native sugars".NATURE (2024).