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.
Original language | English |
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Pages (from-to) | 627-633 |
Number of pages | 7 |
Journal | Journal of Porphyrins and Phthalocyanines |
Volume | 27 |
Issue number | 1-4 |
DOIs | |
Publication status | Published - Jan 2023 |
Keywords
- antivitamin B1 2
- B1 2-Antimetabolite
- corrin
- tetrapyrrole
- transition metal
- vitamin B1 2