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Related Concept Videos

Isomerism02:43

Isomerism

18.0K
Isomers are molecules with the same molecular formula but different structural arrangements. Isomers can be further classified into constitutional isomers and stereoisomers. Constitutional isomers differ in the connectivity of their constituent atoms. For example, 2-butanol and diethyl ether are constitutional isomers, as they have the same chemical formula, C4H10O, but differ in the connectivity of the carbon and oxygen atoms. Constitutional isomers have different physical and chemical...
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Fischer Projections02:18

Fischer Projections

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Learning to draw Fischer projections of molecules and understanding their relevance plays a crucial role in the visual depiction of organic molecules. A Fischer projection is a two-dimensional projection on a planar surface to simplify the three-dimensional wedge–dash representation of molecules. This is especially helpful in the case of molecules with multiple chiral centers that can be difficult to draw. Here, all the bonds of interest are represented as horizontal or vertical lines.
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Insulin: Biosynthesis, Chemistry, and Preparation01:25

Insulin: Biosynthesis, Chemistry, and Preparation

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The endoplasmic reticulum (ER) of pancreatic β-cells synthesizes preproinsulin, which consists of a signal peptide, A and B chains, and a C-peptide. Preproinsulin is then cleaved and folded into proinsulin, which translocates to the Golgi apparatus for sorting and packaging into secretory granules. In these granules, enzymatic clipping generates insulin and C-peptide.
Damage or functional impairment of β-cells inhibits insulin production, leading to diabetes. Diabetes treatment...
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Structural Isomerism02:34

Structural Isomerism

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Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can...
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Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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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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Related Experiment Video

Updated: Jun 17, 2025

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis
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Hierarchical and Programmable One-Pot Oligosaccharide Synthesis

Published on: September 6, 2019

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A concise synthetic approach for isoiminosugars.

Martin Thonhofer1, André Culum1, Tobias Dorn1

  • 1Graz University of Technology, Institute of Chemistry and Technology of Biobased Systems, Stremayrgasse 9, A-8010, Graz, Austria.

Carbohydrate Research
|August 14, 2024
PubMed
Summary

Researchers developed a concise synthesis for biologically active isoiminosugars. This method utilizes a key hydride shift to create C-2 branched glycofuranosides, enabling efficient synthesis of β-galactosidase inhibitors.

Keywords:
4-epi-isofagomineGlycosid hydrolasesInhibitorIsoiminosugarSynthesis

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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
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Related Experiment Videos

Last Updated: Jun 17, 2025

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Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

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Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis
  • Medicinal Chemistry

Background:

  • Isoiminosugars are a class of biologically active compounds with therapeutic potential.
  • Existing synthetic routes for isoiminosugars can be lengthy and complex.
  • Development of efficient synthetic strategies is crucial for accessing these valuable molecules.

Purpose of the Study:

  • To report a concise and efficient synthetic approach for isoiminosugars.
  • To demonstrate the utility of a stereospecific 1,2-hydride shift in synthesizing C-2 branched glycofuranosides.
  • To provide a streamlined synthesis of the potent β-galactosidase inhibitor, 4-epi-isofagomine.

Main Methods:

  • Stereospecific 1,2-hydride shift reaction on O-2 tosylated glycopyranosides.
  • Glycosylation reactions to form branched glycofuranosides.
  • Multi-step synthesis starting from d-glucopyranoside.

Main Results:

  • A novel synthetic route to C-2 branched glycofuranosides was established.
  • The key step involves a stereospecific 1,2-hydride shift, offering high control.
  • A 4-step synthesis of 4-epi-isofagomine was achieved from d-glucopyranoside.

Conclusions:

  • The developed synthetic approach is concise and efficient for producing isoiminosugars.
  • The 1,2-hydride shift is a powerful tool for accessing C-2 branched glycofuranosides.
  • This method provides a practical route to potent β-galactosidase inhibitors like 4-epi-isofagomine.