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Related Concept Videos

Radical Formation: Addition00:47

Radical Formation: Addition

1.7K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
1.7K
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.1K
Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
2.1K
Radical Formation: Elimination00:51

Radical Formation: Elimination

1.7K
Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions...
1.7K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.1K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
5.1K
Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

8.1K
In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
8.1K
Radical Chain-Growth Polymerization: Mechanism01:09

Radical Chain-Growth Polymerization: Mechanism

2.5K
The radical chain-growth polymerization mechanism consists of three steps: initiation, propagation, and termination of polymerization. The polymerization initiates when a free radical generated from the radical initiator adds to the unsaturated bond in the monomer. The unpaired electron of the free radical and one π electron in the unsaturated bond creates a σ bond between the free radical and the monomer. As a result, the other π electron in the unsaturated bond converts this...
2.5K

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High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles
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High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles

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Direct radical functionalization of native sugars.

Yi Jiang1,2,3, Yi Wei1, Qian-Yi Zhou1

  • 1Department of Chemistry, National University of Singapore, Singapore, Singapore.

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Chemists developed a new photoinduced method for direct glycosylation using native sugars. This protecting-group-free approach simplifies complex carbohydrate synthesis and enables direct protein glycosylation.

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Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis
  • Biochemistry

Background:

  • Naturally occurring sugars possess numerous reactive hydroxyl groups, complicating direct chemical modification.
  • Traditional synthesis of complex carbohydrates (glycans) requires laborious protecting-group strategies.
  • Direct, site-selective transformation of native sugars into valuable reagents remains a significant challenge in chemistry.

Purpose of the Study:

  • To develop a novel, protecting-group-free method for site- and stereoselective chemical glycosylation.
  • To enable direct synthesis of complex saccharides from readily available native sugar building blocks.
  • To explore the application of this method in protein glycosylation.

Main Methods:

  • A photoinduced approach utilizing homolytic (one-electron) chemistry was employed.
  • The method involves regiocontrolled generation of a transient glycosyl donor from native sugars.
  • Radical-based cross-coupling with electrophiles is activated by light, bypassing hydroxyl group protection.

Main Results:

  • The 'cap and glycosylate' strategy provides straightforward access to diverse glycosyl compounds.
  • Selective anomeric functionalization of mono- and oligosaccharides was achieved.
  • The developed method demonstrated biocompatibility and was successfully extended to direct post-translational protein glycosylation.

Conclusions:

  • This photoinduced, protecting-group-free method offers a simplified route to complex glycosyl compounds from native sugars.
  • The approach mimics natural processes in its regiocontrolled donor generation and radical-based coupling.
  • The direct glycosylation of proteins represents a significant advancement in bioconjugation and glycobiology.