Synthesis, spectral characterization and crystal structure of Chlororhodibalamin: A synthesis platform for rhodium analogues of vitamin B12 and for Rh-based antivitamins B12

Widner, Florian J., Kieninger, Christoph, Wurst, Klaus, Deery, Evelyne, Lawrence, Andrew D., Warren, Martin J. ORCID: https://orcid.org/0000-0002-6028-6456 and Kräutler, Bernhard (2021) Synthesis, spectral characterization and crystal structure of Chlororhodibalamin: A synthesis platform for rhodium analogues of vitamin B12 and for Rh-based antivitamins B12. Synthesis, 53 (2). pp. 332-337. ISSN 0039-7881

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Abstract

Chlororhodibalamin (ClRhbl), a rhodium analogue of vitamin B12 (cyanocobalamin), was prepared in 84% yield by metalation of the metal-free B12 ligand hydrogenobalamin using the RhI-complex [Rh(CO)2Cl]2. ClRhbl was identified and characterized by UV/Vis, circular dichroism, high-resolution mass and heteronuclear NMR spectra. The RhIII-corrin ClRhbl features the 'base-on' architecture of vitamin B12. X-ray analysis of single crystals of ClRhbl have revealed its detailed 3D-geometry and close structural similarity to the CoIII-analogue chlorocobalamin (ClCbl). ClRhbl is a versatile starting material for the preparation of other rhodibalamins, among them the organometallic derivatives adenosylrhodibalamin and methylrhodibalamin, the Rh analogues of the important coenzyme and cofactor forms of B12, adenosylcobalamin and methylcobalamin.

Item Type: Article
Additional Information: Funding Information: Funding by the Austrian Science Fund (FWF, projects No. P-28892 and P-30359 to BK), as well as by the Biotechnology and Biological Sciences Research Council (BBSRC, grant number BB/S002197/1 to MJW) and Royal Society (INF\R2\180062 to MJW) is gratefully acknowledged.Biotechnologyand Biological SciencesResearch Council(BB/S002197/1)AutianScienceFundP28892AusrianScienceFundP30359)Royal SocieyofBiologyINFR2\180062) Publisher Copyright: © 2021 Georg Thieme Verlag. All rights reserved.
Uncontrolled Keywords: antivitamin,inhibitors,metalation,natural products,porphyrins,rhodium,transition metals,vitamins,catalysis,organic 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
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Depositing User: LivePure Connector
Date Deposited: 21 Sep 2022 08:30
Last Modified: 18 Apr 2023 15:30
URI: https://ueaeprints.uea.ac.uk/id/eprint/88541
DOI: 10.1055/s-0040-1707288

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