1,2-ジパルミトイルフォスファチジルコリン
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/01/19 20:02:19」(JST)
[Wiki en表示]
| Dipalmitoylphosphatidylcholine |
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| Identifiers |
| CAS number |
2644-64-6 Y |
| PubChem |
6138 |
| ChemSpider |
398235 Y |
| UNII |
2W15RT5V7V Y |
| Jmol-3D images |
Image 1 |
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O=C(OC[C@@H](OC(=O)CCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C)CCCCCCCCCCCCCCC
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InChI=1S/C40H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3/t38-/m1/s1 Y
Key: KILNVBDSWZSGLL-KXQOOQHDSA-N Y
InChI=1/C40H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3/t38-/m1/s1
Key: KILNVBDSWZSGLL-KXQOOQHDBV
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| Properties |
| Molecular formula |
C40H80NO8P |
| Molar mass |
734.039 g/mol |
Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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
- Lecithin
- Colfosceril palmitate
- Molecular Dynamics simulation of DPPC lipid bilayer formation in two phase systems
Molecular Dynamics simulation of DPPC lipid bilayer formation in two phase systems
References
- ^ 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. //www.ncbi.nlm.nih.gov/pmc/articles/PMC1544237/.
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Lipids: phospholipids
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Glycerol backbone
(Glycerophospholipids/
Phosphoglycerides) |
Phosphatidyl-: -ethanolamine/cephalin (PE) · -choline/lechithin (PC) · -serine (PS) · -glycerol (PG) · -inositol (PI) (glyco- (GPI))
Phosphoinositides: PIP (PI(3)P, PI(4)P, PI(5)P) · PIP2 (PI(3,4)P2, PI(3,5)P2, PI(4,5)P2) · PIP3
Cardiolipin
Ether lipids: Plasmalogen (Platelet-activating factor)
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| Sphingosine backbone |
Sphingomyelin
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| Metabolites |
Inositol phosphate · Inositol
Lysophosphatidic acid
Choline · Phosphocholine · Citicoline
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mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m
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k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon
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m (A16/C10), i (k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)
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- biochemical families: carbohydrates
- alcohols
- glycoproteins
- glycosides
- lipids
- eicosanoids
- fatty acids / intermediates
- phospholipids
- sphingolipids
- steroids
- nucleic acids
- constituents / intermediates
- proteins
- amino acids / intermediates
- tetrapyrroles / intermediates
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English Journal
- Comparison of three remote radiolabelling methods for long-circulating liposomes.
- van der Geest T1, Laverman P2, Gerrits D2, Franssen GM2, Metselaar JM3, Storm G4, Boerman OC2.
- Journal of controlled release : official journal of the Controlled Release Society.J Control Release.2015 Oct 26;220(Pt A):239-244. doi: 10.1016/j.jconrel.2015.10.043. [Epub ahead of print]
- PMID 26514291
- Development of a Sortase A-mediated Peptide-labeled Liposome Applicable to Drug-delivery Systems.
- Tabata A1, Ohkubo Y1, Anyoji N1, Hojo K2, Tomoyasu T1, Tatematsu Y3, Ohkura K3, Nagamune H4.
- Anticancer research.Anticancer Res.2015 Aug;35(8):4411-7.
- BACKGROUND/AIM: In order to develop an efficient drug-delivery system (DDS), a lipopeptide-loaded liposome that functions as a platform for the transpeptidase reaction mediated by sortase A (SrtA) was constructed and its stability, as well as cell-specific targeting were evaluated in the present stu
- PMID 26168480
- A comparative calorimetric and spectroscopic study of the effects of cholesterol and of the plant sterols β-sitosterol and stigmasterol on the thermotropic phase behavior and organization of dipalmitoylphosphatidylcholine bilayer membranes.
- Mannock DA1, Benesch MG1, Lewis RN1, McElhaney RN2.
- Biochimica et biophysica acta.Biochim Biophys Acta.2015 Aug;1848(8):1629-38. doi: 10.1016/j.bbamem.2015.04.009. Epub 2015 Apr 22.
- We performed comparative DSC and FTIR spectroscopic measurements of the effects of β-sitosterol (Sito) and stigmasterol (Stig) on the thermotropic phase behavior and organization of DPPC bilayers. Sito and Stig are the major sterols in the biological membranes of higher plants, whereas cholesterol
- PMID 25911208
Japanese Journal
- Characteristic interactivity of landiolol, an ultra-short-acting highly selective β1-blocker, with biomimetic membranes: Comparisons with β1-selective esmolol and non-selective propranolol and alprenolol.
- Cardiotoxic Local Anesthetics Increasingly Interact with Biomimetic Membranes under Ischemia-Like Acidic Conditions
Related Links
- InChI=1S/C40H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42) 46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21- 19-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3/t38-/m1/s1 Yes Y ...
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