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A Triazole Bioisostere-Based Approach to Understanding Ceramide Amide Bond Conformation and Function
- Kim, Seonghun;
- Kim, Mi Jeong;
- Han, Jaeho;
- Kim, Jae Hyun;
- Lee, Sang Kook;
- 외 4명
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0초록
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. © 2025 Wiley‐VCH GmbH.
키워드
1,2,3‐triazole; bioisostere; ceramide; cis–trans amide; CYCLOADDITION; SPHINGOLIPIDS; METABOLISM
- 제목
- A Triazole Bioisostere-Based Approach to Understanding Ceramide Amide Bond Conformation and Function
- 저자
- Kim, Seonghun; Kim, Mi Jeong; Han, Jaeho; Kim, Jae Hyun; Lee, Sang Kook; Koh, Eun Hee; Yoo, Hyun Ju; Lee, Hyunji; Kim, Sanghee
- 발행일
- 2025-11
- 유형
- Article; Early Access