Phytosphingosine and Sphingosine Ceramide Headgroup Hydrogen Bonding: Structural Insights through Thermotropic Hydrogen/Deuterium Exchange

Autor:	Patrick Garidel, Dina Van Wyck, Hui-Chen Chen, David J. Moore, Berislav Marković, Mark E. Rerek, and Richard Mendelsohn
Rok vydání:	2001
Předmět:	Ceramide Sphingosine Chemistry Stereochemistry Hydrogen bond Thermotropic crystal Surfaces Coatings and Films chemistry.chemical_compound medicine.anatomical_structure Scissoring Materials Chemistry Stratum corneum medicine Molecule Hydrogen–deuterium exchange Physical and Theoretical Chemistry
Zdroj:	The Journal of Physical Chemistry B. 105:9355-9362
ISSN:	1520-5207 1520-6106
DOI:	10.1021/jp0118367
Popis:	IR spectroscopic studies are reported for the phytosphingosine class of ceramides and are compared with two analogous sphingosine ceramides. The phytosphingosine class of molecules, not previously widely investigated by physical techniques, constitutes ∼30% of the total ceramide content of the stratum corneum, the barrier to permeability in skin. The current measurements utilize temperature-controlled horizontal attenuated total reflectance spectroscopy of hydrated films to study H → D exchange in the polar regions of the molecules as well as chain conformational order and packing properties. Analysis of the methylene stretching and scissoring vibrations reveals that the chains of the two phytosphingosine derivatives (ceramides 3 and 7) are much more poorly packed at room temperature than their sphingosine counterparts (ceramides 2 and 5 respectively), despite having order → disorder transitions some 15−20 degrees higher. This unanticipated relative stability of the phytosphingosines is traced to enhanced...
Databáze:	OpenAIRE
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