Macrocycles model lipids

Macrocyclic model lipids for the formation of vesicles often contain four ester bonds— two on each head group. It has been found that these ester bonds are exceptionally stable against acid-catalyzed hydrolysis in water. The reasons probably lie in the partial hydrophobicity of the ester group s environment, the macrocycle s order, and the reversibility of ester hydrolysis. Partially hydrolyzed tetraesters are presumably immediately reformed in vesicular membrane structures before the second, third, and fourth ester group reacts (Scheme 2.4.9). 

We have already reported that synthetic peptide lipids, having ot-amino acid residuefs) interposed between a polar head moiety and a hydrophobic doublechain segment, can be used as models for functional simulation of biomembranes [23]. On this ground, we are to clarify molecular recognition specificity by supramolecular assemblies formed in combination of the macrocyclic receptors with the peptide lipid as artificial cell-surface receptors. 

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