Synthesis, structure, and thermal properties of 1,2-dipalmitoylgalloylglycerol (DPGG), a novel self-adhering lipid

A novel diacyl glycerol-based lipid with a polyphenolic head group has been synthesized and characterized. X-ray diffraction experiments show that this lipid, 1,2-dipalmitoylgalloylglycerol (DPGG), hydrates to form gel phase bilayers at 20°C with extremely narrow interbilayer fluid separations, indi...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry and physics of lipids 2000, Vol.104 (1), p.67-74
Main Authors: Pollastri, M.P., Porter, N.A., McIntosh, T.J., Simon, S.A.
Format: Article
Language:English
Subjects:
Adhesion
Calorimetry
Calorimetry, Differential Scanning
Diglycerides - chemical synthesis
Diglycerides - chemistry
Hydrogen Bonding
Lipid Bilayers
Molecular Structure
Polyphenol
Thermodynamics
X-Ray Diffraction
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A novel diacyl glycerol-based lipid with a polyphenolic head group has been synthesized and characterized. X-ray diffraction experiments show that this lipid, 1,2-dipalmitoylgalloylglycerol (DPGG), hydrates to form gel phase bilayers at 20°C with extremely narrow interbilayer fluid separations, indicating that apposing DPGG bilayers strongly adhere to each other. Differential scanning calorimetry shows that fully hydrated DPGG exhibits a pretransition exotherm (3.7 kcal/mol) at 52°C and a high enthalpy (11.3 kcal/mol) main endothermic transition at 69°C. These thermal properties are similar to those of galactosylceramides with similar hydrocarbon chain compositions. The adhesive and thermal properties of DPGG are likely due to both intermolecular hydrogen-bonding and hydrophobic interactions between the aromatic rings on the gallic acids.
ISSN:0009-3084
1873-2941
DOI:10.1016/S0009-3084(99)00110-3