Some Aspects of the Metabolism of Sulfur-Containing Heterocyclic Cofactors: Lipoic Acid, Biotin, and 8α-(S-L-Cysteinyl)Riboflavin

Hydrophobic interactions as structure determining factors for macromolecules are wellknown in biochemistry. Considerably less recognized is the fact that these low-energy interactions may also determine the structure of low-molecular species. The same applies for weak ligand-metal ion interactions. That both these factors may lead to intramolecular, concentration-independent equilibria between isomeric metal-ion complexes is demonstrated with a-lipoic acid as ligand. This cofactor offers metal ions two different binding sites: the carboxylate group and the disulfide linkage. The carboxylate group dominates the coordinating properties of this ligand towards the biologically important metal ions, but a disulfide-metal ion interaction is still possible and under sterically favorable conditions may become very important; this could also be true under enzymic conditions where the carboxyl group is no longer free but amide-linked to the protein. Furthermore, due to the valeric acid side chain, the lipoyl moiety is ideally suited to undergo hydrophobic ligand-ligand interactions in mixed-ligand complexes. Such hydrophobic interactions seem to be ideal to allow migration, e . g . , of the 14 A long lipoyllysyl moiety, and also to facilitate the correct 'fixation' at the surface of the enzyme.

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Some Aspects of the Metabolism of Sulfur-Containing Heterocyclic Cofactors: Lipoic Acid, Biotin, and 8α-(S-L-Cysteinyl)Riboflavin

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References 22 publications

Die hydrophoben und Metallionen-koordinierenden Eigenschaften von α-Liponsäure - ein Beispiel für intramolekulare Gleichgewichte in Metallionen-Komplexen

Die hydrophoben und Metallionen-koordinierenden Eigenschaften von α-Liponsäure - ein Beispiel für intramolekulare Gleichgewichte in Metallionen-Komplexen

The Hydrophobic and Metal‐Ion Coordinating Properties of α‐Lipoic Acid—An Example of Intramolecular Equilibria in Metal‐Ion Complexes

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