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Stabilizing intramolecular cobalt–imidazole coordination with a remote methyl group in the backbone of a cofactor B12–protein model


Sonnay, Marjorie; Zelder, Felix (2018). Stabilizing intramolecular cobalt–imidazole coordination with a remote methyl group in the backbone of a cofactor B12–protein model. Dalton Transactions, 47(31):10443-10446.

Abstract

This communication describes the stabilizing effect (ΔΔG° = −4 kJ mol$^{^−1}$) of a remote methyl group in the backbone of a cobalamin–enzyme mimic on intramolecular imidazole–cobalt coordination. For this purpose, two B12 derivatives with an appended imidazole base were synthesized and analysed with spectrophotometric pH titrations. Qualitative conformation analysis of the backbone structure suggests that a thermodynamically unfavoured gauche interaction in the base-off form of a model containing an (R)-configured CH3 group at position C176 of the linker between the corrin ring and the terminal imidazole ligand steers the base toward cobalt coordination.

Abstract

This communication describes the stabilizing effect (ΔΔG° = −4 kJ mol$^{^−1}$) of a remote methyl group in the backbone of a cobalamin–enzyme mimic on intramolecular imidazole–cobalt coordination. For this purpose, two B12 derivatives with an appended imidazole base were synthesized and analysed with spectrophotometric pH titrations. Qualitative conformation analysis of the backbone structure suggests that a thermodynamically unfavoured gauche interaction in the base-off form of a model containing an (R)-configured CH3 group at position C176 of the linker between the corrin ring and the terminal imidazole ligand steers the base toward cobalt coordination.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1 January 2018
Deposited On:12 Dec 2019 10:04
Last Modified:29 Feb 2020 08:23
Publisher:Royal Society of Chemistry
ISSN:1477-9226
OA Status:Green
Publisher DOI:https://doi.org/10.1039/c8dt01298a
Project Information:
  • : FunderSNSF
  • : Grant ID200021-117822
  • : Project TitleModified B12 derivatives as novel inhibitors of B12 dependant enzymes and allosteric catalysts

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