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Glycerophospholipid


DATA No : PGP2001 INFORMANT : Masahiro Nishijima

NAME : 1,2-diacyl-sn-glycero-3-phosphorylcholine/phosphatidylcholine

COMMON NAME: lecithin
SYMBOL: PC/PtdCho
FORMULA: MOL.WT (average) :


Download ChemDraw structure data
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:Insoluble but swells up in water and in NaCl solution forming a colloidal suspension. Soluble in about 12 parts cold, absolute alcohol; soluble in chloroform, ether, petr ether, in mineral oils and fatty acids; sparingly soluble in benzene. Insolble in acetone; practically insoluble in cold vegetable and animal oils.
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

[Chromatogram 0001]
SOURCE
PC is one of the principal phospholipids of mammalian tissues(Ref. 2001/2002/2003/2004/2005/2006/2007) and plants(Ref. 2008). It is generally absent from heterotrophic bacteria and hence, fails to qualify as a universal membrane constituent(Ref. 2009/2010). PC was first described by Gobley in 1847 as a component of egg yolk and named 'lecithin' after the Greek equivalent for egg yolk (lekithos).
CHEMICAL SYNTHESIS
The first confirmation of this structure came through chemical synthesis of the correct enantiomeric form by Baer and Kates(Ref. 2011). Chemical synthesis of PC has been achieved by the reacylation(with specific acyl chlorides) of GPC (as its CdCl2 complex) derived from the large scale deacylation of pure PC(Ref. 2012). Other syntheses follow routes similar to those for PA up to the formation of the phosphorylated derivative. In the synthesis of PC the phosphate is blocked except for one reactive chloro-or hydroxyl group which can then be reacted with appropriate reagents to give the choline substituent(Ref. 2012/2013).
METABOLISM
In fungal microorganisms, as in other eukaryotes, there are two pathways for PC biosynthesis(Ref. 2014). In mammals, the major route for synthesis of PC is the CDP-choline pathway, while the methylation pathway apparently contributes to the synthesis of PC only in the liver(Ref. 2015). In CDP-choline pathway, free choline is phosphorylated and converted to CDP-choline, and then the phosphocholine moiety of CDP-choline is transferred to diacylglycerol for PtdCho formation. CDP-choline formation is rate limiting for PtdCho biosynthesis. In yeast and other fungi, however, the methylation pathway serves as the principle route for PC biosynthesis especially in cells growing in the absence of choline supp;ementation.
Under these conditions, PC is synthesized via a series of three sequential methylations of PE, catalyzed by the membrane-associated phospholipid N-methyltransferases(PLMTs). The two intermediates in this reaction series have been identified as PMME and phosphatidyl-dimethylethanolamine(PDME). Fungi, in contrast to mammals, have two PLMTs. Plants do not methylate PE, but can carry out the last two methylation steps to PC biosynthesis from PMME(Ref. 2016)
GENETIC INFORMATION
Cloning of genes or cDNA for enzymes involved in PtdCho biosynthesis. yeast choline kinase(Ref. 2018), human choline kinase(Ref. 2019), rat choline kinase(Ref. 2020/2021), yeast CTP:phosphocholine sytidyltransferase(Ref. 2022), rat CTP:phosphocholine sytidyltransferase(Ref. 2023), yeast PE-methyltransferases(Ref. 2024), rat PE-methyltransferases(Ref. 2025)
NOTE

REFERENCES
[2001]
AUTHOR:Rouser,G.,and Yamamoto,A.
TITLE:
JOURNAL:Lipids
VOL:3 PAGE : 284 - (1968)
[TOP]

[2002]
AUTHOR:Rouser, G., and Solomon, R. D.
TITLE:Changes in phospholipid composition of human aorta with age PubMed ID:4306676
JOURNAL:Lipids.
VOL:4 PAGE : 232-234 (1969)
[TOP]

[2003]
AUTHOR:Baxter, C. F., Rouser, G., and Simon, G.
TITLE:Variations among vertebrates of lung phospholipid case composition PubMed ID:4306679
JOURNAL:Lipids.
VOL:4 PAGE : 243-244 (1969)
[TOP]

[2004]
AUTHOR:Rouser, G., Simon, G., and Kritchevsky, G.
TITLE:Species variations in phospholipid class distribution of organs. I. Kidney, liver and spleen PubMed ID:5367944
JOURNAL:Lipids.
VOL:4 PAGE : 599-606 (1969)
[TOP]

[2005]
AUTHOR:Simon,G.and Rouser,G.
TITLE:Species variations in phospholipid class distribution of organs. II. Heart and skeletal muscle. PubMed ID:5367945
JOURNAL:Lipids
VOL:4 PAGE : 607 -614 (1969)
[TOP]

[2006]
AUTHOR:Williams,J.H.,Kuchmak,M.,and Witter,R.F.
TITLE:
JOURNAL:Lipids
VOL:1 PAGE : 89 - ()
[TOP]

[2007]
AUTHOR:Williams,J.H.,Kuchmak,M.,and Witter,R.F.
TITLE:
JOURNAL:Lipids
VOL:1 PAGE : 391 - (1966)
[TOP]

[2008]
AUTHOR:Kates,M.
TITLE:
JOURNAL:Advan. Lipid Res.
VOL:8 PAGE : 225 - (1970)
[TOP]

[2009]
AUTHOR:Goldfine,H.
TITLE:Lipid chemistry and metabolism. PubMed ID:4299228
JOURNAL:Ann. Rev. Biochem.
VOL:37 PAGE : 303 -330 (1968)
[TOP]

[2010]
AUTHOR:Ikawa, M.
TITLE:Bacterial phosphatides and natural relationships PubMed ID:5342712
JOURNAL:Bacteriol Rev.
VOL:31 PAGE : 54-64 (1967)
[TOP]

[2011]
AUTHOR:Baer,E. (1963) Progress in the Chemistry of Fats and other Lipids (Holman, R.T.,Lundberg,W.O., and Malkin,T., eds), pp33, Pergamon, London
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[2012]
AUTHOR:Slotboom,A.J., and Bonsen,P.P.M.
TITLE:Recent developments in the chemistry of phospholipids. PubMed ID:5498118
JOURNAL:Chem. Phys. Lipids
VOL:5 PAGE : 301 -397 (1970)
[TOP]

[2013]
AUTHOR:van Deenen,L.L.M., and de Haas,G.H.
TITLE:
JOURNAL:Advan. Lipid Res.
VOL:2 PAGE : 167 - (1964)
[TOP]

[2014]
AUTHOR:Esko,J.D.,and Raetz,C.R.H.
TITLE:Mutants of Chinese Hamster Ovary Cells with Altered Membrane Phospholipid Composition. PubMed ID:7372588
JOURNAL:J. Biol. Chem.
VOL:255 PAGE : 4474 -4480 (1980)
[TOP]

[2015]
AUTHOR:Kent, C.
TITLE:Eukaryotic phospholipid biosynthesis PubMed ID:7574485
JOURNAL:Annu Rev Biochem.
VOL:64 PAGE : 315-343 (1995)
[TOP]

[2016]
AUTHOR:Vance,D.E. (1996) Glycerolipid biosynthesis in eukaryotes, in New Comprehensive Biochemistry, vol.31, Biochemistry of Lipids, Lipoproteins and Membranes (Vance,D.E., and Vance,J.E., eds), pp153-181, Elsevier Science B.V., Amsterdam
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[2018]
AUTHOR:Hosaka, K., Kodaki, T., and Yamashita, S.
TITLE:Cloning and characterization of the yeast CKI gene encoding choline kinase and its expression in Escherichia coli PubMed ID:2536698
JOURNAL:J Biol Chem.
VOL:264 PAGE : 2053-2059 (1989)
[TOP]

[2019]
AUTHOR:Hosaka, K., Tanaka, S., Nikawa, J., and Yamashita, S.
TITLE:Cloning of a human choline kinase cDNA by complementation of the yeast cki mutation PubMed ID:1618328
JOURNAL:FEBS Lett.
VOL:304 PAGE : 229-232 (1992)
[TOP]

[2020]
AUTHOR:Uchida, T., and Yamashita, S.
TITLE:Molecular cloning, characterization, and expression in Escherichia coli of a cDNA encoding mammalian choline kinase PubMed ID:1577786
JOURNAL:J Biol Chem.
VOL:267 PAGE : 10156-10162 (1992)
[TOP]

[2021]
AUTHOR:Uchida, T.
TITLE:Regulation of choline kinase R: analyses of alternatively spliced choline kinases and the promoter region PubMed ID:7852267
JOURNAL:J Biochem (Tokyo).
VOL:116 PAGE : 508-518 (1994)
[TOP]

[2022]
AUTHOR:Tsukagoshi, Y., Nikawa, J., and Yamashita, S.
TITLE:Molecular cloning and characterization of the gene encoding cholinephosphate cytidylyltransferase in Saccharomyces cerevisiae PubMed ID:2826147
JOURNAL:Eur J Biochem.
VOL:169 PAGE : 477-486 (1987)
[TOP]

[2023]
AUTHOR:Kalmar, G. B., Kay, R. J., Lachance, A., Aebersold, R., and Cornell, R. B.
TITLE:Cloning and expression of rat liver CTP: phosphocholine cytidylyltransferase: an amphipathic protein that controls phosphatidylcholine synthesis PubMed ID:2166941
JOURNAL:Proc Natl Acad Sci U S A.
VOL:87 PAGE : 6029-6033 (1990)
[TOP]

[2024]
AUTHOR:Kodaki,T.,and Yamashita,S.
TITLE:Yeast phosphatidylethanolamine methylation pathway. PubMed ID:2445736
JOURNAL:J. Biol. Chem.
VOL:262 PAGE : 15428 -15435 (1987)
[TOP]

[2025]
AUTHOR:Vance, D. E., and Ridgway, N. D.
TITLE:The methylation of phosphatidylethanolamine PubMed ID:3057511
JOURNAL:Prog Lipid Res.
VOL:27 PAGE : 61-79 (1988)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.