Abstract
The complex ion of nonactin potassium shows a highly regular spheric structure which was deduced from an X-ray structural analysis, as shown by Prof. Simon. The macrocyclic ligand is folded in the manner of the seam of a tennis ball. It can easily be seen, and it can be shown by means of models, that such a regular shape (and hence a high complex stability) is only possible if the building stones of nonactin are arranged in a stereochemical manner which is unique in natural products: The macrocyclic ring is composed of 4 nonactinic acid residues, two of them have the (+)-configuration, the other two the enantiomeric ( — )-configuration, so that nonactin itself is, in spite of the presence of 16 asymmetric carbon atoms, an achiral meso-compound.
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© 1969 Springer-Verlag Berlin · Heidelberg
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Keller-Schierlein, W. (1969). Stereochemical Aspects of Macrotetrolide Action and Biosynthesis. In: Bücher, T., Sies, H. (eds) Inhibitors Tools in Cell Research. Colloquium der Gesellschaft für Biologische Chemie in Mosbach Baden, vol 20. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-46158-3_31
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DOI: https://doi.org/10.1007/978-3-642-46158-3_31
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