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Open AccessJournal ArticleDOI

Chemical reporters for biological discovery

Markus Grammel, +1 more
- 01 Aug 2013 - 
- Vol. 9, Iss: 8, pp 475-484
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TLDR
How chemical reporters in conjunction with bioorthogonal labeling methods can be used to image and retrieve nucleic acids, proteins, glycans, lipids and other metabolites in vitro, in cells as well as in whole organisms is reviewed.
Abstract
Functional tools are needed to understand complex biological systems. Here we review how chemical reporters in conjunction with bioorthogonal labeling methods can be used to image and retrieve nucleic acids, proteins, glycans, lipids and other metabolites in vitro, in cells as well as in whole organisms. By tagging these biomolecules, researchers can now monitor their dynamics in living systems and discover specific substrates of cellular pathways. These advances in chemical biology are thus providing important tools to characterize biological pathways and are poised to facilitate our understanding of human diseases.

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Changes in Metabolic Chemical Reporter Structure Yield a Selective Probe of O-GlcNAc Modification

TL;DR: It is demonstrated here that 6-azido-6-deoxy-N-acetyl-glucosamine (6AzGlcNAc) is a specific MCR for O- GlcNAcylated proteins, and results suggest that specific M CRs for other types of glycosylation can be developed.
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1,2,4-Triazines Are Versatile Bioorthogonal Reagents.

TL;DR: A new class of bioorthogonal reagents, 1,2,4-triazines, capable of robust reactivity with trans-cyclooctene (TCO) and enhanced stability of the triazine scaffold enabled its direct use in recombinant protein production.
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Orthogonal bioorthogonal chemistries.

TL;DR: The development of orthogonal bioorthogonal reactions and their application in multi-target imaging and macromolecule assembly are highlighted, along with prospects for identifying new classes of compatible reactions.
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Transition-metal-mediated uncaging in living human cells—an emerging alternative to photolabile protecting groups.

TL;DR: Metal catalysts based on palladium, ruthenium and iron are discussed and their biocompatibility and catalytic efficiency in uncaging reactions within biological environments are discussed.
Journal ArticleDOI

Metabolic Remodeling of Cell-Surface Sialic Acids: Principles, Applications, and Recent Advances

TL;DR: The metabolic glycan labeling (MGL) strategy has emerged as an invaluable chemical biology tool that enables metabolic installation of useful functionalities into cell‐surface sialoglycans by “hijacking” the sialic acid biosynthetic pathway.
References
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Journal ArticleDOI

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TL;DR: In this paper, a set of powerful, highly reliable, and selective reactions for the rapid synthesis of useful new compounds and combinatorial libraries through heteroatom links (C-X-C), an approach called click chemistry is defined, enabled, and constrained by a handful of nearly perfect "springloaded" reactions.
Journal ArticleDOI

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Journal ArticleDOI

Tet proteins can convert 5-methylcytosine to 5-formylcytosine and 5-carboxylcytosine

TL;DR: This study raises the possibility that DNA demethylation may occur through Tet-catalyzed oxidation followed by decarboxylation, and identifies two previously unknown cytosine derivatives in genomic DNA as the products of Tet proteins.
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Tet-Mediated Formation of 5-Carboxylcytosine and Its Excision by TDG in Mammalian DNA

TL;DR: It is demonstrated that 5mC and 5hmC in DNA are oxidized to 5-carboxylcytosine (5caC) by Tet dioxygenases in vitro and in cultured cells, suggesting that oxidation of 5m C by Tet proteins followed by TDG-mediated base excision of 5caC constitutes a pathway for active DNA demethylation.
Journal ArticleDOI

1,3-Dipolar Cycloadditions. Past and Future†

TL;DR: In contrast to the very large number of special methods applicable to syntheses in the heterocyclic series, relatively few general methods are available as discussed by the authors, and the 1,3-dipolar addition offers a remarkably wide range of utility in the synthesis of five-membered heterocycles.
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