Document Detail


The total synthesis of 2-O-arachidonoyl-1-O-stearoyl-sn-glycero-3-phosphocholine-1,3,1'-(13)C3 and -2,1'-(13)C2 by a novel chemoenzymatic method.
MedLine Citation:
PMID:  19682980     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
2-O-Arachidonoyl-1-O-stearoyl-sn-glycero-3-phosphocholine was synthesized with carbon-13 enrichment of the three glycerol carbons and the carbonyl of the stearoyl group. Phospholipase A(2) was utilized to give optically pure lyso-PC, and only 3% acyl migration occurred during reacylation with arachidonic acid anhydride. This phospholipid is an important biosynthetic precursor of arachidonic acid metabolites as well as the endocannabinoid 2-arachidonoylglycerol (2-AG), and is now available for NMR studies.
Authors:
Richard I Duclos
Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural    
Journal Detail:
Title:  Chemistry and physics of lipids     Volume:  163     ISSN:  1873-2941     ISO Abbreviation:  Chem. Phys. Lipids     Publication Date:  2010 Jan 
Date Detail:
Created Date:  2009-12-16     Completed Date:  2010-02-24     Revised Date:  2014-09-21    
Medline Journal Info:
Nlm Unique ID:  0067206     Medline TA:  Chem Phys Lipids     Country:  Ireland    
Other Details:
Languages:  eng     Pagination:  102-9     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Arachidonic Acid / metabolism
Arachidonic Acids / metabolism
Carbon Isotopes / chemistry
Endocannabinoids
Glycerides / metabolism
Isotope Labeling / methods
Magnetic Resonance Spectroscopy
Phosphatidylcholines / chemical synthesis*,  chemistry
Phospholipases A / metabolism
Grant Support
ID/Acronym/Agency:
DA-24842/DA/NIDA NIH HHS; HL-26335/HL/NHLBI NIH HHS; P01 HL026335/HL/NHLBI NIH HHS; P01 HL026335-179001/HL/NHLBI NIH HHS; P01 HL026335-189001/HL/NHLBI NIH HHS; P01 HL026335-199001/HL/NHLBI NIH HHS; P01 HL026335-209001/HL/NHLBI NIH HHS; P01 HL026335-219001/HL/NHLBI NIH HHS; P01 HL026335-229001/HL/NHLBI NIH HHS; P01 HL026335-239001/HL/NHLBI NIH HHS; P01 HL026335-249001/HL/NHLBI NIH HHS; P01 HL026335-259001/HL/NHLBI NIH HHS; R03 DA024842/DA/NIDA NIH HHS; R03 DA024842-01/DA/NIDA NIH HHS; R03 DA024842-02/DA/NIDA NIH HHS
Chemical
Reg. No./Substance:
0/Arachidonic Acids; 0/Carbon Isotopes; 0/Endocannabinoids; 0/Glycerides; 0/Phosphatidylcholines; 18892-74-5/1-stearoyl-2-arachidonylphosphatidylcholine; 27YG812J1I/Arachidonic Acid; 53847-30-6/2-arachidonylglycerol; EC 3.1.1.-/Phospholipases A
Comments/Corrections

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