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Kieninger, Christoph, Deery, Evelyne, Lawrence, Andrew D., Warren, Martin J. 
ORCID: https://orcid.org/0000-0002-6028-6456 and Kräutler, Bernhard
(2023)
Hydrogenobinamide and nibinamide-Metal-free ligand and Ni(II)-Analogue of the vitamin B1 2 precursor cobinamide.
Journal of Porphyrins and Phthalocyanines, 27 (1-4).
pp. 627-633.
ISSN 1088-4246
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Abstract
The replacement of cobalt in vitamin B12 derivatives by other transition metals is a formal path to non-natural corrins. Here, we describe nibinamide (Nibi), the novel Ni(II)-Analogue of the natural B12-derivative cobinamide (Cbi), and its synthesis from the metal-free ligand of Cbi, hydrogenobinamide (Hbi), both isolated as tetrafluoroborate salts. Aqueous solutions of the metal-free corrin Hbi are strongly fluorescent, whereas its Ni(II)-complex Nibi is non-luminescent. The solution structures of Hbi and of Nibi were characterized by hetero-nuclear NMR-spectroscopy. The Ni(II)-corrin Nibi was deduced to be roughly iso-structural to cob(I)inamide (CbiI) and to house a diamagnetic d8-metal-ioniso-electronic to CoI in CbiI. The chemically robust Nibi is, thus, a structural mimic of enzyme-Activated and reduced biosynthetic precursors of vitamin B12 and a B12-Antimetabolite potentially functioning as a specific inhibitor of B12-biosynthesis.
| Item Type: | Article |
|---|---|
| Additional Information: | Acknowledgments: This work was supported by grants from the Austria Science Fund (FWF, P-28892 and P33059) to BK and from the Biotechnology and Biological Sciences Research Council (BBSRC) BB/S002197/1 to MJW. Supporting information: Figures of CD-, fluorescence and mass spectra, and NMR-data are given in the supplementary material. This material is available free of charge via the Internet at https://www.worldscientific.com/doi/suppl/10.1142/S1088424623500463 |
| Uncontrolled Keywords: | antivitamin b1 2,b1 2-antimetabolite,corrin,tetrapyrrole,transition metal,vitamin b1 2,chemistry(all) ,/dk/atira/pure/subjectarea/asjc/1600 |
| Faculty \ School: | Faculty of Science |
| UEA Research Groups: | Faculty of Medicine and Health Sciences > Research Centres > Norwich Institute for Healthy Aging |
| Related URLs: | |
| Depositing User: | LivePure Connector |
| Date Deposited: | 29 Oct 2024 14:30 |
| Last Modified: | 04 Nov 2024 12:30 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/97337 |
| DOI: | 10.1142/S1088424623500463 |
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