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Updated: Jan 11, 2026
Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
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.
Abstract:
The amide bond of ceramide can adopt either a cis or trans conformation, but the biological relevance of this geometry remains unclear. We used 1,4- and 1,5-disubstituted 1,2,3-triazoles as conformationally restricted bioisosteres to investigate the functional consequences of amide bond geometry. Antiproliferative assays, sphingomyelin synthase 1 metabolite profiling, and molecular docking analyses all indicate that the trans conformation better reflects the biologically active state. These findings provide direct evidence that amide bond conformation plays a critical role in ceramide function.
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