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Updated: Jan 11, 2026
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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
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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
Summary
Ceramide
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.
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