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Volumn 11, Issue 13, 2009, Pages 2784-2787

Synthesis and antioxidant properties of an unnatural plasmalogen analogue bearing a trans O-vinyl ether linkage

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ANTIOXIDANT; FREE RADICAL; IRIDIUM; PLASMALOGEN; VINYL DERIVATIVE; VINYL ETHER;

EID: 67649476252     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9009078     Document Type: Article
Times cited : (14)

References (48)
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    • A semisynthetic route to racemic trans-1 via a lipase-catalyzed hydrolysis of an l-(alkenyloxy)-2,3-diacylglycerol was reported: Slotboom, A. J.; De Haas, G. H.; van Deenen, L. L. M. Chem. Phys. Lipids 1967, 1, 192-208.
    • A semisynthetic route to racemic trans-1 via a lipase-catalyzed hydrolysis of an l-(alkenyloxy)-2,3-diacylglycerol was reported: Slotboom, A. J.; De Haas, G. H.; van Deenen, L. L. M. Chem. Phys. Lipids 1967, 1, 192-208.
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    • Primary amines react with HOCl to give chloramines; therefore, we synthesized 1 with a phosphocholine instead of a phosphoethanolamine head group to target the O-vinyl ether linkage in the HOCl reaction and avoid having a competing reactive site
    • Messner, M. C.; Albert, C. J.; Hsu, F. F.; Ford, D. A. Chem. Phys. Lipids 2006, 144, 34-44. Primary amines react with HOCl to give chloramines; therefore, we synthesized 1 with a phosphocholine instead of a phosphoethanolamine head group to target the O-vinyl ether linkage in the HOCl reaction and avoid having a competing reactive site.
    • (2006) Chem. Phys. Lipids , vol.144 , pp. 34-44
    • Messner, M.C.1    Albert, C.J.2    Hsu, F.F.3    Ford, D.A.4
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    • For syntheses of mixtures of l-O-(l'-alkenyl)glycerols and 2-O(l'-alkenyl)glycerols containing E/Z mixtures, see:
    • For syntheses of mixtures of l-O-(l'-alkenyl)glycerols and 2-O(l'-alkenyl)glycerols containing E/Z mixtures, see:
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    • 2-mediated opening of glycidyl derivatives with saturated aliphatic alcohols, see:
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    • 3 (4:1) containing 1 μM NaOH, and analyzed by ESI-MS (flow rate, 3 μL/min). Samples were analyzed in the positive ion mode with detection of their sodiated adducts.
    • 3 (4:1) containing 1 μM NaOH, and analyzed by ESI-MS (flow rate, 3 μL/min). Samples were analyzed in the positive ion mode with detection of their sodiated adducts.
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    • To correct for changes in A234 arising from AAPH-induced plasmalogen oxidation, liposomes were prepared with only cis- or trans-1 at the same concentrations present in the 16:0- 18:2-PC + 1 liposomes.
    • To correct for changes in A234 arising from AAPH-induced plasmalogen oxidation, liposomes were prepared with only cis- or trans-1 at the same concentrations present in the 16:0- 18:2-PC + 1 liposomes.


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