Issue 77, 2016

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

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

Supplementary files

Article information

Article type
Paper
Submitted
27 Jun 2016
Accepted
21 Jul 2016
First published
27 Jul 2016

RSC Adv., 2016,6, 73343-73350

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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