Chemistry

Ciba Foundation Symposium 158 - Host-Guest Molecular

Composed of contributions from specialists within the chemical and organic sciences, it explores host-guest molecular interactions resulting in the formation of molecular assemblies containing or extra species. interesting purposes are rising during this box and it really is anticipated that more suitable knowing of the interactions in man made host molecule complexes will result in a greater realizing of the extra advanced organic platforms. themes contain biomimetic chemistry, preorganization, self-assembly, template-directed synthesis, antibiotic binding to peptides and DNA, interactions among proteins and different molecules.

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Sometimes there is a quite remarkable difference in the strength of the enthalpic interaction between two complexes that have exactly the same stability constant. Of course, this is related to changes in solvent order. In any event, I agree that the magnitude of the enthalpy and the balance of enthalpy and entropy can be critical for the overall success of binding and transport. Dunitz: The stability constant is a ratio of two rates; the need for a good on-rate puts limitations on the off-rate.

What must be the spacing of the three rings to fit a membrane? How far can a cation jump? That is, would a single, central ring be sufficient or would other ‘relay points’ be required? What would be the role of water in such a system? It seemed to us that the first question requiring to be answered was whether or not a crown ether could serve as the head group for synthetic bilayer (vesicle) formation. This question was answered by the preparation (Gokel et a1 1987) and aggregation (Echegoyen et a1 1988) of aza-15-crown-5 attached to a steroid via a glycine res,idue.

0 0 3 Having satisfied ourselves that a crown ether could serve effectively as the head group in a lipid bilayer we resolved to undertake the syntheses of several related structures. The question of span length next required consideration. Fortunately, X-ray crystal structures of the gramicidin A system were recently reported by Wallace & Ravikumar (1989) and Langs (1989) and their data are summarized in Table 1 . The structure of gramicidin A is O=CH-L-Val-Gly-L- Ala-D-Leu-L-Ala-D-Val-L-Val-D-Val-L-Trp-D-Leu-L-Trp-D-Leu-L-Trp Leu-L-Trp-ethanolamine.

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