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

No Thumbnail Available
Authors
Alliband, Amanda M.
Meece, Frederick A.
Jayasinghe, Champika P.
Burns, Dennis H.
Advisors
Issue Date
2013-01-18
Type
Article
Keywords
HOST-DEFENSE PEPTIDES , ANTIMICROBIAL PEPTIDES , MOLECULES , POLYMERS , POTENT
Research Projects
Organizational Units
Journal Issue
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.

Table of Contents
Description
Click on the DOI link to access the article (may not be free).
Publisher
American Chemical Society
Journal
Book Title
Series
Journal of Organic Chemistry;v.78 no.2
PubMed ID
DOI
ISSN
0022-3263
EISSN