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Pyridinio-isoalloxazinophanes as model systems for active-site complexes in flavoenzymes: syntheses, X-ray structure analyses and spectroscopic properties

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Staab,  Heinz A.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Krieger,  Claus
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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http://onlinelibrary.wiley.com/doi/10.1002/cber.19941270918/epdf
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https://doi.org/10.1002/cber.19941270918
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Citation

Staab, H. A., Zipplies, M. F., Müller, T., Storch, M., & Krieger, C. (1994). Pyridinio-isoalloxazinophanes as model systems for active-site complexes in flavoenzymes: syntheses, X-ray structure analyses and spectroscopic properties. Chemische Berichte, 127(9), 1667-1680. doi:10.1002/cber.19941270918.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0019-A8D5-E
Abstract
As model systems for active site complexes in flavoenzymes, flavin and nicotinamide analogues were linked together in cyclophane skeletons of specific sterical structures. Elaborating this concept, we prepared [4]metacyclo[3](10,6)isoalloxazinophane (3), [4](3,1)pyridino[3](10,6)isoalloxazinophane (4), as well as the 16-methoxycarbonyl and the 16-carboxylato derivatives (2 and 34, resp.), of 4 by multistep syntheses. For the isoalloxazinophanes 2, 3, 4, and 34 X-ray structure analyses were performed and are discussed with regard to intramolecular interactions. Preliminary UV/Vis-spectroscopic results related to π…π interactions in these isoalloxazinophanes are reported.