Dipalmitoylphosphatidylcholine

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Dipalmitoylphosphatidylcholine
Identifiers
CAS number 2644-64-6 YesY
PubChem 6138
ChemSpider 398235 YesY
UNII 2W15RT5V7V YesY
Jmol-3D images {{#if:O=C(OC[C@@H](OC(=O)CCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C)CCCCCCCCCCCCCCC|Image 1
Properties
Molecular formula C40H80NO8P
Molar mass 734.039 g/mol
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Dipalmitoylphosphatidylcholine (DPPtdCho) is a phospholipid (and a lecithin) consisting of two palmitic acids and is the major constituent of pulmonary surfactant. It is also the only surface active component of lung surfactant capable of lowering surface tension to near zero levels. DPPtdCho is synthesized mainly through remodeling of phosphatidylcholine.

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.[1] 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. ↑ 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 1544237. PMID 16864775. 
Glycerol backbone
(Glycerophospholipids/
Phosphoglycerides)
Phosphatidyl-:
Phosphoinositides:
Ether lipids:
Sphingosine backbone
Metabolites

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m (A16/C10), i (k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

  • Biochemical families: carbohydrates
    • alcohols
    • glycoproteins
    • glycosides
  • lipids
    • eicosanoids
    • fatty acids / intermediates
    • phospholipids
    • sphingolipids
    • steroids
  • nucleic acids
    • constituents / intermediates
  • proteins
    • Amino acids / intermediates
  • tetrapyrroles / intermediates

DPPC molecule is zwitteronic having a negative charge on the phosphate group and a positive charge on the amine

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