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Issue 11, 2021
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Synthesis and characterization of bichromophoric 1-deoxyceramides as FRET probes

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Abstract

The suitability as FRET probes of two bichromophoric 1-deoxydihydroceramides containing a labelled spisulosine derivative as a sphingoid base and two differently ω-labelled fluorescent palmitic acids has been evaluated. The ceramide synthase (CerS) catalyzed metabolic incorporation of ω-azido palmitic acid into the above labeled spisulosine to render the corresponding ω-azido 1-deoxyceramide has been studied in several cell lines. In addition, the strain-promoted click reaction between this ω-azido 1-deoxyceramide and suitable fluorophores has been optimized to render the target bichromophoric 1-deoxydihydroceramides. These results pave the way for the development of FRET-based assays as a new tool to study sphingolipid metabolism.

Graphical abstract: Synthesis and characterization of bichromophoric 1-deoxyceramides as FRET probes

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Article information


Submitted
21 Jan 2021
Accepted
22 Feb 2021
First published
23 Feb 2021

This article is Open Access

Org. Biomol. Chem., 2021,19, 2456-2467
Article type
Paper

Synthesis and characterization of bichromophoric 1-deoxyceramides as FRET probes

E. Izquierdo, M. Casasampere, G. Fabriàs, J. L. Abad, J. Casas and A. Delgado, Org. Biomol. Chem., 2021, 19, 2456
DOI: 10.1039/D1OB00113B

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