Solution, crystal and in silico structures of the organometallic vitamin B12-derivative acetylcobalamin and of its novel rhodium-analogue acetylrhodibalamin

Wiedemair, Markus, Kieninger, Christoph, Wurst, Klaus, Podewitz, Maren, Deery, Evelyne, Paxhia, Michael D., Warren, Martin J. and Kräutler, Bernhard (2023) Solution, crystal and in silico structures of the organometallic vitamin B12-derivative acetylcobalamin and of its novel rhodium-analogue acetylrhodibalamin. Helvetica Chimica Acta, 106 (2). ISSN 0018-019X

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Abstract

The natural vitamin B12-derivatives are intriguing complexes of cobalt that entrap the metal within the strikingly skewed and ring-contracted corrin ligand. Here, we describe the synthesis of the Rh(III)-corrin acetylrhodibalamin (AcRhbl) from biotechnologically produced metal-free hydrogenobyric acid and analyze the effect of the replacement of the cobalt-center of the organometallic vitamin B12-derivative acetylcobalamin (AcCbl) with its group-IX homologue rhodium, to give AcRhbl. The structures of AcCbl and AcRhbl were thoroughly analyzed in aqueous solution, in crystals and by in silico methods, in order to gain detailed insights into the structural adaptations to the two homologous metals. Indeed, the common, nucleotide-appended corrin-ligand in these two metal corrins features extensive structural similarity. Thus, the rhodium-corrin AcRhbl joins the small group of B12-mimics classified as ‘antivitamins B12’, isostructural metal analogues of the natural cobalt-corrins that hold significant potential in biological and biomedical applications as selective inhibitors of key cellular processes.

Item Type:	Article
Additional Information:	Funding Information: The authors thank the Austrian Science Fund (FWF) for financial support to B. K. (project P 33059) and to M. P. (project P 33528) and to the Biotechnology & Biological Sciences Research Council (BBSRC) (project numbers BB/S002197/1 and BB/X001946/1) to M. J. W.
Uncontrolled Keywords:	antivitamin b,cobalt,corrin,density functional calculations,organometallic chemistry,rhodium,salmonella,transition metals,x-ray diffraction,catalysis,biochemistry,drug discovery,physical and theoretical chemistry,organic chemistry,inorganic chemistry ,/dk/atira/pure/subjectarea/asjc/1500/1503
Faculty \ School:	Faculty of Science
UEA Research Groups:	Faculty of Medicine and Health Sciences > Research Centres > Norwich Institute for Healthy Aging
Related URLs:	http://www.scopus.com/inward/record.url?...
Depositing User:	LivePure Connector
Date Deposited:	31 Oct 2024 12:30
Last Modified:	01 Apr 2025 00:22
URI:	https://ueaeprints.uea.ac.uk/id/eprint/97372
DOI:	10.1002/hlca.202200158

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