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Issue 77, 2016
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Synthesis of 6-hydroxyceramide using ruthenium-catalyzed hydrosilylation–protodesilylation. Unexpected formation of a long periodicity lamellar phase in skin lipid membranes

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Abstract

The synthesis of a ceramide with a 6-hydroxysphingosine base, a unique component of the human epidermal barrier, is reported. The key step involves a mild and selective trans-reduction of a triple bond using [Cp*Ru(CH3CN)3]PF6-catalyzed hydrosilylation followed by protodesilylation. The oxidation of sphingosine-based ceramide to 6-hydroxyceramide is also described. X-Ray powder diffraction on the model skin lipid membranes showed that 6-hydroxyceramide promotes the formation of a lamellar phase with 10.6 nm periodicity, which might explain why keratinocytes hydroxylate some ceramides at carbon 6.

Graphical abstract: Synthesis of 6-hydroxyceramide using ruthenium-catalyzed hydrosilylation–protodesilylation. Unexpected formation of a long periodicity lamellar phase in skin lipid membranes

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Article information


Submitted
27 Jun 2016
Accepted
21 Jul 2016
First published
27 Jul 2016

RSC Adv., 2016,6, 73343-73350
Article type
Paper

Synthesis of 6-hydroxyceramide using ruthenium-catalyzed hydrosilylation–protodesilylation. Unexpected formation of a long periodicity lamellar phase in skin lipid membranes

A. Kováčik, L. Opálka, M. Šilarová, J. Roh and K. Vávrová, RSC Adv., 2016, 6, 73343
DOI: 10.1039/C6RA16565F

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