Phosphorylated Monomolecular Layers : Design, Synthesis, Characterization and Application

• This thesis describes the design, synthesis and characterization of organo-phosphatemonomolecular layers, so called self-assembled monolayers, using the strategy of linking organosulfur substances to a gold surface. Moreover there is also a paper included, which describes the development of synthetic pathways to various phospholipids, for which I have developed an interest in later projects.For the first study of the properties of phosphates, and also for concomitant application of developed systems, analogues of the amino acids serine, threonine and tyrosine, phosphorylated and non-phosphorylated, were synthesized. 16-Mercaptohexadecanamide based analogues were characterized as monolayers and large polar and charge effects were observed, introduced by the phosphate. Problems were, however, encountered as a post modification of phosphates was applied and a disordering of the monolayers observed. Moreover there were no expected effects observable upon interaction with Ca2+ and Mg2+.Based on the conclusions from the first study 3-mercaptopropionamide based analogues were used instead. Characterization of the analogues including counter ion exchange (H+,Na+, Ca2+ and Mg2+) revealed large electronic and possible structural differences depending on the counter ion.Again the charge and polar effects induced by the phosphate were investigated, and the study was also extended to interaction of the phosphate with Ca2+ and Mg2+. Strong effects were observed, which were also dependent on the ion concentration within a significant range. The polarity and charge properties of the phosphate layer were thus found to be variable.In the fourth study an additional Ca2+ and Mg2+ sensitive system was applied in combination with the phosphate surface. Phosphate surface/phospholipid vesicle interactions were studied under different conditions of Mg2+ (Ca2+) treatment. For comparison, the corresponding hydroxyl and sulphate surfaces were included and also the most well characterized surface concerning phospholipid vesicle interaction, SiO2. Most importantly, supported phospholipid bilayer (SPB) formation was found to be inducible on both the phosphate and sulphate surfaces, however at defined conditions of Mg2+ (Ca2+) treatment and concentration. The conclusion is that the processes of phospholipid vesicle adsorption and SPB formation are largely dependent on vesicle/surface interaction and vesicle stability.The last paper included in this thesis is a synthetic method development aimed at easy preparations of various phospholipid derivatives. In the future these methods could be used for synthesis of functionalized lipids and aid in the development of models mimicking biological systems such as artificial cell membranes.

Ämnesord

NATURVETENSKAP  -- Kemi -- Fysikalisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Physical Chemistry (hsv//eng)

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