Chemical remodeling of cell-surface sialic acids through a palladium-triggered bioorthogonal elimination reaction

Angewandte Chemie
Jie WangPeng R Chen

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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Citations

Feb 18, 2016·Nature Chemical Biology·Jie Li, Peng R Chen
Sep 29, 2015·National Science Review·Chuan He
Nov 1, 2016·Journal of the American Chemical Society·Jie WangPeng R Chen
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