Synthesis, spectral characterization and crystal structure of chlororhodibalamin: a synthesis platform for rhodium analogues of vitamin B12 and for Rh-based antivitamins B12
Synthesis, spectral characterization and crystal structure of chlororhodibalamin: a synthesis platform for rhodium analogues of vitamin B12 and for Rh-based antivitamins B12
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.
332-337
Widner, Florian J.
0477b58a-559d-440a-8f97-1a860cfa2b44
Kieninger, Christoph
9d3d3f90-edb8-42cb-90cb-ebd119e437a7
Wurst, Klaus
1e8623f8-6db2-48b5-b5c7-58c191d19ab3
Deery, Evelyne
16c10c8d-1383-4ce6-95dd-dfcfa0168875
Lawrence, Andrew D.
ce503b40-0155-486f-bb1d-26830b61b5f1
Warren, Martin J.
5f601da9-9516-4a76-8dbd-fc399648cd99
Kräutler, Bernhard
a9f1114e-990d-4209-bd52-998dbdee8838
Widner, Florian J.
0477b58a-559d-440a-8f97-1a860cfa2b44
Kieninger, Christoph
9d3d3f90-edb8-42cb-90cb-ebd119e437a7
Wurst, Klaus
1e8623f8-6db2-48b5-b5c7-58c191d19ab3
Deery, Evelyne
16c10c8d-1383-4ce6-95dd-dfcfa0168875
Lawrence, Andrew D.
ce503b40-0155-486f-bb1d-26830b61b5f1
Warren, Martin J.
5f601da9-9516-4a76-8dbd-fc399648cd99
Kräutler, Bernhard
a9f1114e-990d-4209-bd52-998dbdee8838
Widner, Florian J., Kieninger, Christoph, Wurst, Klaus, Deery, Evelyne, Lawrence, Andrew D., Warren, Martin J. and Kräutler, Bernhard
(2020)
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), .
(doi:10.1055/s-0040-1707288).
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.
Text
s-0040-1707288
- Version of Record
More information
Accepted/In Press date: 27 August 2020
e-pub ahead of print date: 5 October 2020
Identifiers
Local EPrints ID: 488401
URI: http://eprints.soton.ac.uk/id/eprint/488401
ISSN: 0039-7881
PURE UUID: 29c09dac-6644-4ef6-82e0-7245122b8e61
Catalogue record
Date deposited: 21 Mar 2024 17:43
Last modified: 22 Mar 2024 03:05
Export record
Altmetrics
Contributors
Author:
Florian J. Widner
Author:
Christoph Kieninger
Author:
Klaus Wurst
Author:
Evelyne Deery
Author:
Andrew D. Lawrence
Author:
Martin J. Warren
Author:
Bernhard Kräutler
Download statistics
Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.
View more statistics