Dipalmitoylphosphatidylcholine

Dipalmitoylphosphatidylcholine
Identifiers
2644-64-6 YesY
3D model (Jmol) Interactive image
ChemSpider 398235 YesY
ECHA InfoCard 100.018.322
PubChem 6138
UNII 2W15RT5V7V YesY
Properties
C40H80NO8P
Molar mass 734.039 g/mol
Surface tension:
4.6 ± 0.5 x 10−10 M[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Dipalmitoylphosphatidylcholine (DPPtdCho) is a phospholipid (and a lecithin) consisting of two palmitic acids attached of a phosphatidylcholine head-group and is the major constituent of many pulmonary surfactants. It is zwitterionic by virtue of having a negative charge on the phosphate group and a positive charge on the quaternary ammonium group.

It is thought that a lysophosphatidylcholine (lysoPC) acyltransferase may play a critical role in its synthesis. The identity of this acyltransferase has not yet been confirmed.[2] Dipalmitoylphosphatidylcholine is an exception to the rule of thumb that biological phospholipids are synthesized with a saturated fat at the R1 position and an unsaturated fat at the R2 position.

It is also used for research purposes in studying liposomes, lipid bilayers, and model biological membranes and in the formation of reconstituted HDL (rHDL) particles.

See also

A laminar system consisting of water and gas molecules separated by DPPC lipid layers
Molecular Dynamics simulation of DPPC lipid bilayer formation in two phase systems

References

  1. ↑ Smith, Ross; Tanford, Charles (June 1972). "The critical micelle concentration of l-α-dipalmitoylphosphatidylcholine in water and water/methanol solutions". Journal of Molecular Biology. 67 (1): 75–83. doi:10.1016/0022-2836(72)90387-7.
  2. ↑ Chen, Xueni; Hyatt, BA; Mucenski, ML; Mason, RJ; Shannon, JM (2006). "Identification and characterization of a lysophosphatidylcholine acyltransferase in alveolar type II cells". Proc Natl Acad Sci USA. 103 (31): 11724–11729. doi:10.1073/pnas.0604946103. PMC 1544237Freely accessible. PMID 16864775.


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