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Related Concept Videos

SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
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Protein glycosylation starts in the ER lumen and continues in the Golgi apparatus. Glycosyltransferases catalyze the addition of sugar molecules or glycosylation of proteins. Usually, these enzymes add sugars to the hydroxyl groups of selected serine or threonine residues to form O-linked glycans or the amino groups of asparagine residues to form N-linked glycans. Different positions on the same polypeptide chain can contain differently linked glycans.
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Naming Enantiomers02:21

Naming Enantiomers

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The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system...
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Prochirality02:05

Prochirality

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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Regioselectivity and Stereochemistry of Hydroboration02:36

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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Stereoisomers02:32

Stereoisomers

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On the basis of mirror symmetry, stereoisomers of an organic molecule can be further classified into diastereomers and enantiomers. Diastereomers are stereoisomers that are not mirror images of each other. Substituted alkenes, such as the cis and trans isomers of 2-butene, are diastereomers, as these molecules exhibit different spatial orientations of their constituent atoms, are not mirror images of each other, and do not interconvert. Here, the interconversion is suppressed due to...
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Stereoselective Approaches to β-Linked 2-Deoxy Sugars.

Clay S Bennett1

  • 1Department of Chemistry, Tufts University, 62 Talbot Ave, Medford, MA 02155, USA.

Molecules (Basel, Switzerland)
|April 26, 2025
PubMed
Summary

This review explores recent advances in synthesizing β-linked 2-deoxy sugars, covering catalytic and de novo methods from the past decade. It discusses applications, mechanisms, and future directions for these crucial carbohydrate structures.

Keywords:
catalysisglycosylationnatural productsstereoselectivitysynthesis

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Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis

Background:

  • 2-deoxy sugars are vital components of biologically active molecules.
  • Efficient synthesis of β-linked isomers remains a challenge.

Purpose of the Study:

  • To review recent synthetic methodologies for β-linked 2-deoxy sugars.
  • To highlight advancements in the last 10 years.
  • To discuss applications and future prospects.

Main Methods:

  • Catalytic approaches
  • De novo synthesis strategies
  • Glycosylation techniques

Main Results:

  • Overview of diverse synthetic routes.
  • Discussion of catalytic efficiency and stereoselectivity.
  • Examples of successful applications in complex molecule synthesis.

Conclusions:

  • Recent synthetic methods offer improved access to β-linked 2-deoxy sugars.
  • Further research is needed to expand scope and address limitations.
  • The field is poised for continued innovation in carbohydrate synthesis.