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

Publication ,  Journal Article
Pollastri, MP; Porter, NA; McIntosh, TJ; Simon, SA
Published in: Chem Phys Lipids
January 2000

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.

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Published In

Chem Phys Lipids

DOI

ISSN

0009-3084

Publication Date

January 2000

Volume

104

Issue

1

Start / End Page

67 / 74

Location

Ireland

Related Subject Headings

  • X-Ray Diffraction
  • Thermodynamics
  • Molecular Structure
  • Lipid Bilayers
  • Hydrogen Bonding
  • Diglycerides
  • Calorimetry, Differential Scanning
  • Biophysics
  • 3205 Medical biochemistry and metabolomics
  • 3101 Biochemistry and cell biology
 

Citation

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Pollastri, M. P., Porter, N. A., McIntosh, T. J., & Simon, S. A. (2000). Synthesis, structure, and thermal properties of 1,2-dipalmitoylgalloylglycerol (DPGG), a novel self-adhering lipid. Chem Phys Lipids, 104(1), 67–74. https://doi.org/10.1016/s0009-3084(99)00110-3
Pollastri, M. P., N. A. Porter, T. J. McIntosh, and S. A. Simon. “Synthesis, structure, and thermal properties of 1,2-dipalmitoylgalloylglycerol (DPGG), a novel self-adhering lipid.Chem Phys Lipids 104, no. 1 (January 2000): 67–74. https://doi.org/10.1016/s0009-3084(99)00110-3.
Pollastri MP, Porter NA, McIntosh TJ, Simon SA. Synthesis, structure, and thermal properties of 1,2-dipalmitoylgalloylglycerol (DPGG), a novel self-adhering lipid. Chem Phys Lipids. 2000 Jan;104(1):67–74.
Pollastri, M. P., et al. “Synthesis, structure, and thermal properties of 1,2-dipalmitoylgalloylglycerol (DPGG), a novel self-adhering lipid.Chem Phys Lipids, vol. 104, no. 1, Jan. 2000, pp. 67–74. Pubmed, doi:10.1016/s0009-3084(99)00110-3.
Pollastri MP, Porter NA, McIntosh TJ, Simon SA. Synthesis, structure, and thermal properties of 1,2-dipalmitoylgalloylglycerol (DPGG), a novel self-adhering lipid. Chem Phys Lipids. 2000 Jan;104(1):67–74.
Journal cover image

Published In

Chem Phys Lipids

DOI

ISSN

0009-3084

Publication Date

January 2000

Volume

104

Issue

1

Start / End Page

67 / 74

Location

Ireland

Related Subject Headings

  • X-Ray Diffraction
  • Thermodynamics
  • Molecular Structure
  • Lipid Bilayers
  • Hydrogen Bonding
  • Diglycerides
  • Calorimetry, Differential Scanning
  • Biophysics
  • 3205 Medical biochemistry and metabolomics
  • 3101 Biochemistry and cell biology