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Related Concept Videos

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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Structures of Carboxylic Acid Derivatives01:28

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Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
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Conformations of Cyclohexane02:11

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Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...
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Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

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Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
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Stability of Conjugated Dienes01:28

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Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
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Assembly of the Lipid Bilayer in the ER01:28

Assembly of the Lipid Bilayer in the ER

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Biological membranes are more than just a barrier separating cell cytoplasm from the outside environment. They are highly dynamic and help maintain the integrity and physiological stability of the cells as well as membrane-bound organelles. Membranes also play vital roles in cell-to-cell and intracellular communication.
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A Triazole Bioisostere-Based Approach to Understanding Ceramide Amide Bond Conformation and Function.

Seonghun Kim1, Mi Jeong Kim2, Jaeho Han1,3

  • 1College of Pharmacy, Seoul National University, Seoul, Republic of Korea.

Chemistry, an Asian Journal
|November 14, 2025
PubMed
Summary

Ceramide

Keywords:
1,2,3‐triazolebioisostereceramidecis–trans amide

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Area of Science:

  • Lipid biochemistry
  • Molecular biology
  • Medicinal chemistry

Background:

  • Ceramides are essential lipids with diverse biological roles.
  • The amide bond in ceramides can exist in cis or trans conformations.
  • The functional significance of ceramide amide bond geometry is not well understood.

Purpose of the Study:

  • To investigate the functional impact of ceramide amide bond conformation.
  • To determine which amide bond geometry (cis or trans) is biologically relevant.
  • To utilize conformationally restricted bioisosteres for studying ceramide function.

Main Methods:

  • Synthesis of 1,4- and 1,5-disubstituted 1,2,3-triazoles as rigid ceramide analogs.
  • Antiproliferative assays to assess biological activity.
  • Sphingomyelin synthase 1 metabolite profiling.
  • Molecular docking analyses to predict binding interactions.

Main Results:

  • The trans conformation of the ceramide amide bond was identified as the biologically active state.
  • Conformationally restricted triazole bioisosteres mimicked the functional effects of specific ceramide geometries.
  • Data from antiproliferative assays, metabolite profiling, and docking supported the trans conformation's relevance.

Conclusions:

  • Amide bond conformation is a critical determinant of ceramide biological function.
  • The trans conformation represents the functionally relevant state for ceramides.
  • This study provides direct evidence for the importance of stereochemistry in ceramide activity.