Journal Article10.1021/JA044996F
A Strain-Promoted [3 + 2] Azide−Alkyne Cycloaddition for Covalent Modification of Biomolecules in Living Systems
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TL;DR: A strain-promoted [3 + 2] cycloaddition between cyclooctynes and azides that proceeds under physiological conditions without the need for a catalyst was demonstrated by selective modification of biomolecules in vitro and on living cells, with no apparent toxicity.
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Abstract: Selective chemical reactions that are orthogonal to the diverse functionality of biological systems have become important tools in the field of chemical biology. Two notable examples are the Staudinger ligation of azides and phosphines and the Cu(I)-catalyzed [3 + 2] cycloaddition of azides and alkynes (“click chemistry”). The Staudinger ligation has sufficient biocompatibility for performance in living animals but suffers from phosphine oxidation and synthetic challenges. Click chemistry obviates the requirement of phosphines, but the Cu(I) catalyst is toxic to cells, thereby precluding in vivo applications. Here we present a strain-promoted [3 + 2] cycloaddition between cyclooctynes and azides that proceeds under physiological conditions without the need for a catalyst. The utility of the reaction was demonstrated by selective modification of biomolecules in vitro and on living cells, with no apparent toxicity.
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Citations
Polysaccharides: The “Click” Chemistry Impact
Pierre-Henri Elchinger,Pierre-Antoine Faugeras,Benjamin Boëns,François Brouillette,Daniel Montplaisir,Rachida Zerrouki,Romain Lucas +6 more
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Recent Trends in Bioorthogonal Click-Radiolabeling Reactions Using Fluorine-18
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Injectable hyaluronic acid/poly(ethylene glycol) hydrogels crosslinked via strain-promoted azide-alkyne cycloaddition click reaction.
TL;DR: The injectable hyaluronic acid (HA)-based hydrogels crosslinked with azide-modified poly(ethylene glycol) (PEG) via the strain-promotedAzide-alkyne cycloaddition (SPAAC) between cyclooctyne and azide groups have good mechanical properties and biocompatibility and would be useful in a wide range of applications.
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References
Cell Surface Engineering by a Modified Staudinger Reaction
Eliana Saxon,Carolyn R. Bertozzi +1 more
TL;DR: A chemical transformation that permits the selective formation of covalent adducts among richly functionalized biopolymers within a cellular context is presented and should permit its execution within a cell's interior, offering new possibilities for probing intracellular interactions.
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Chemical remodelling of cell surfaces in living animals
TL;DR: It is demonstrated that the Staudinger ligation can be executed in living animals, enabling the chemical modification of cells within their native environment and may enable therapeutic targeting and non-invasive imaging of changes in glycosylation during disease progression.
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A chemical approach for identifying O-GlcNAc-modified proteins in cells
TL;DR: A chemical strategy directed toward identifying O-GlcNAc-modified proteins from living cells or proteins modified in vitro is described, in vitro, that each enzyme in the hexosamine salvage pathway, and the enzymes that affect this dynamic modification, tolerate analogues of their natural substrates in which the N-acyl side chain has been modified to bear a bio-orthogonal azide moiety.
557
Sulfotransferases of Two Specificities Function in the Reconstitution of High Endothelial Cell Ligands for L-selectin
Annette Bistrup,Sunil Bhakta,Jin Kyu Lee,Yevgeniy Y. Belov,Michael D. Gunn,Fengrong Zuo,Chiao-Chain Huang,Reiji Kannagi,Steven D. Rosen,Stefan Hemmerich +9 more
TL;DR: L-selectin, a lectin-like receptor, mediates rolling of lymphocytes on high endothelial venules (HEVs) in secondary lymphoid organs by interacting with HEV ligands, candidates for which are glycosylation- dependent cell adhesion molecule 1 (GlyCAM-1), CD34, and podocalyxin.
Metabolic Functionalization of Recombinant Glycoproteins
TL;DR: In this paper, metabolic oligosaccharide engineering was used to introduce a bioorthogonal functional group, the azide, into cellular and recombinant glycoproteins for subsequent chemical elaboration via Staudinger ligation.
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