Abstract
The title macrotetrolide contains two maleic diester units that add hydrophilic sulfur nucleophiles, e.g., bisulfite, thioacetic acid, and various thioglycosides, in high yield. Two-headed amphiphiles (“bolaamphiphiles” or “bolytes”) are thus formed. They produce extremely thin (hydrophobic part ~20 A) monolayer lipid membrane (MLMs) vesicles, which have been characterized by electron microscopy. Vesicle MLMs produce well-resolved 1H NMR spectra at room temperature, indicating fluidity. Such thin vesicle membranes can be effectively perforated with monensin pyromellitate to give water channels. They can be made unsymmetric; they resist fusion. The ester linkages are protected against acid- or base-catalyzed hydrolysis reactions within the membrane. Surface monolayer properties of some bolytes and the crystallization of a pure diastereomer of a sugar pentaacetate amphiphile are reported.
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