Direct radical functionalization of native sugars

Yi Jiang, Yi Wei, Qian-Yi Zhou, Guo-Quan Sun, Xia-Ping Fu, Nikita Levin, Yijun Zhang, Wen-Qiang Liu, NingXi Song, Shabaz Mohammed, Benjamin G. Davis () and Ming Joo Koh ()
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Yi Jiang: National University of Singapore
Yi Wei: National University of Singapore
Qian-Yi Zhou: National University of Singapore
Guo-Quan Sun: National University of Singapore
Xia-Ping Fu: Harwell Science and Innovation Campus
Nikita Levin: Harwell Science and Innovation Campus
Yijun Zhang: National University of Singapore
Wen-Qiang Liu: National University of Singapore
NingXi Song: National University of Singapore
Shabaz Mohammed: Harwell Science and Innovation Campus
Benjamin G. Davis: Harwell Science and Innovation Campus
Ming Joo Koh: National University of Singapore

Nature, 2024, vol. 631, issue 8020, 319-327

Abstract: Abstract Naturally occurring (native) sugars and carbohydrates contain numerous hydroxyl groups of similar reactivity1,2. Chemists, therefore, rely typically on laborious, multi-step protecting-group strategies3 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.

Date: 2024
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DOI: 10.1038/s41586-024-07548-0

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