Chemical Remodeling of Cell‐Surface Sialic Acids through a Palladium‐Triggered Bioorthogonal Elimination Reaction |
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| Authors: | Jie Wang Bo Cheng Jie Li Zhaoyue Zhang Weiyao Hong Prof?Dr Xing Chen Prof?Dr Peng R Chen |
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| Institution: | 1. Synthetic and Functional Biomolecules Center, Beijing National Laboratory for Molecular Sciences, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871 (China);2. Peking‐Tsinghua Center for Life Sciences, Beijing (China);3. Academy for Advanced Interdisciplinary Studies, Peking University (China) |
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| Abstract: | We herein report a chemical decaging strategy for the in situ generation of neuramic acid (Neu), a unique type of sialic acid, on live cells by the use of a palladium‐mediated bioorthogonal elimination reaction. Palladium nanoparticles (Pd NPs) were found to be a highly efficient and biocompatible depropargylation catalyst for the direct conversion of metabolically incorporated N‐(propargyloxycarbonyl)neuramic acid (Neu5Proc) into Neu on cell‐surface glycans. This conversion chemically mimics the enzymatic de‐N‐acetylation of N‐acetylneuramic acid (Neu5Ac), a proposed mechanism for the natural occurrence of Neu on cell‐surface glycans. The bioorthogonal elimination was also exploited for the manipulation of cell‐surface charge by unmasking the free amine at C5 to neutralize the negatively charged carboxyl group at C1 of sialic acids. |
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| Keywords: | bioorthogonal elimination cell surfaces metabolic oligosaccharide engineering palladium sialic acids |
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