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    Synthesis and characterization of picket porphyrin receptors that bind phosphatidylglycerol, an anionic phospholipid found in bacterial membranes

    Date
    2013-01-18
    Author
    Alliband, Amanda M.
    Meece, Frederick A.
    Jayasinghe, Champika P.
    Burns, Dennis H.
    Metadata
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    Citation
    Alliband, Amanda M.; Meece, Frederick A.; Jayasinghe, Champika; Burns, Dennis H. 2013. Synthesis and characterization of picket porphyrin receptors that bind phosphatidylglycerol, an anionic phospholipid found in bacterial membranes. Journal of Organic Chemistry, v.78 no.2 pp.356-362
    Abstract
    The lipid binding ability of four urea-picket porphyrins designed to bind to both the phosphate anion portion as well as the glycerol hydroxyl groups of phosphatidylglycerol (PG) has been investigated. Isothermal titration calorimetry (ITC) and H-1 NMR were used to determine the receptor's stoichiometry of binding, association constants, and both the enthalpy and entropy of binding with the PG anion. Spectral evidence shows that the phosphate anion portion of PG is hydrogen bonded to the urea groups of the receptors. This binding interaction orients the PG anion in the receptor pocket such that its glycerol hydroxyl groups can align with a third urea picket, and results are furnished that suggest this multifunctional interaction does occur. The structure of the entire picket was found to influence the enthalpy and entropy of lipid binding. The synthesis of tetrabutlyammonium phosphatidylglycerol (TBAPG), and a detailed spectral characterization of its headgroup, is also presented.
    Description
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    URI
    http://dx.doi.org/10.1021/jo302228w
    http://hdl.handle.net/10057/5625
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