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 degrees 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 degrees C and a high enthalpy (11.3 kcal/mol) main endothermic transition at 69 degrees 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.
Pollastri
M P
MP
Department of Chemistry, Duke University, Durham, NC 27706, USA.
Porter
N A
NA
McIntosh
T J
TJ
Simon
S A
SA
D002152:Calorimetry, Differential Scanning; D004075:Diglycerides / Q000138:chemical synthesis* / Q000737:chemistry*; D006860:Hydrogen Bonding; D008051:Lipid Bilayers; D015394:Molecular Structure; D013816:Thermodynamics; D014961:X-Ray Diffraction
C404744:1,2-dipalmitoylgalloylglycerol; D004075:Diglycerides; D008051:Lipid Bilayers