Combined spectroscopic/computational studies of vitamin B12 precursors: geometric and electronic structures of cobinamides.

Inorganic Chemistry
Amanda J ReigThomas C Brunold

Abstract

Vitamin B(12) (cyanocobalamin) and its biologically active derivatives, methylcobalamin and adenosylcobalamin, are members of the family of corrinoids, which also includes cobinamides. As biological precursors to cobalamins, cobinamides possess the same structural core, consisting of a low-spin Co(3+) ion that is ligated equatorially by the four nitrogens of a highly substituted tetrapyrrole macrocycle (the corrin ring), but differ with respect to the lower axial ligation. Specifically, cobinamides possess a water molecule instead of the nucleotide loop that coordinates axially to Co(3+)cobalamins via its dimethylbenzimidazole (DMB) base. Compared to the cobalamin species, cobinamides have proven much more difficult to study experimentally, thus far eluding characterization by X-ray crystallography. In this study, we have utilized combined quantum mechanics/molecular mechanics (QM/MM) computations to generate complete structural models of a representative set of cobinamide species with varying upper axial ligands. To validate the use of this approach, analogous QM/MM geometry optimizations were carried out on entire models of the cobalamin counterparts for which high-resolution X-ray structural data are available. The accuracy ...Continue Reading

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Citations

Jan 1, 2014·Inorganic Chemistry·Jing ZhouJerry M Parks
Feb 16, 2017·Chemistry : a European Journal·Maksymilian KarczewskiDorota Gryko
Jul 6, 2017·Journal of the American Chemical Society·Anastasia C ManesisHannah S Shafaat
Sep 30, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ewa MachalskaMalgorzata Baranska
Jul 31, 2013·The Journal of Physical Chemistry. B·Dorota Rutkowska-ZbikGrażyna Stochel
Jul 9, 2014·Inorganic Chemistry·Ivan G Pallares, Thomas C Brunold
Nov 20, 2020·Inorganic Chemistry·Megan J TodaPawel M Kozlowski

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