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

Journal Article (Journal Article)

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.

Full Text

Duke Authors

Cited Authors

  • Pollastri, MP; Porter, NA; McIntosh, TJ; Simon, SA

Published Date

  • January 2000

Published In

Volume / Issue

  • 104 / 1

Start / End Page

  • 67 - 74

PubMed ID

  • 10660213

International Standard Serial Number (ISSN)

  • 0009-3084

Digital Object Identifier (DOI)

  • 10.1016/s0009-3084(99)00110-3


  • eng

Conference Location

  • Ireland