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. 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.

Keywords

• ceramide
• synthesis
• 6-hydroxysphingosine
• skin barrier