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  Selective utilization of benzimidazolyl-norcobamides as cofactors by the tetrachloroethene reductive dehalogenase of Sulfurospirillum multivorans

Keller, A., Kunze, D., Bommer, L., Paetz, C., Menezes, R. C., Svatoš, A., et al. (2018). Selective utilization of benzimidazolyl-norcobamides as cofactors by the tetrachloroethene reductive dehalogenase of Sulfurospirillum multivorans. Journal of Bacteriology, 200(8): e00584-17. doi:10.1128/JB.00584-17.

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NMR254s1.pdf (Supplementary material), 2MB
 
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 Creators:
Keller, Agathe, Author              
Kunze, David, Author              
Bommer, L., Author              
Paetz, Christian1, Author              
Menezes, Riya Christina2, Author              
Svatoš, Aleš2, Author              
Dobbek, Holger, Author
Schubert, Torsten, Author
Affiliations:
1Research Group Biosynthesis / NMR, MPI for Chemical Ecology, Max Planck Society, ou_421898              
2Research Group Mass Spectrometry, MPI for Chemical Ecology, Max Planck Society, ou_421899              

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 Abstract: The organohalide-respiring bacterium Sulfurospirillum multivorans produces a unique cobamide, namely, norpseudo-B12, which serves as cofactor of the tetrachloroethene (PCE) reductive dehalogenase (PceA). As previously reported, a replacement of the adeninyl moiety, the lower base of the cofactor, by exogenously applied 5,6-dimethylbenzimidazole led to inactive PceA. To explore the general effect of benzimidazoles on the PCE metabolism, the susceptibility of the organism for guided biosynthesis of various singly substituted benzimidazolyl-norcobamides was investigated, and their use as cofactor by PceA was analyzed. Exogenously applied 5-methylbenzimidazole (5-MeBza), 5-hydroxybenzimidazole (5-OHBza), and 5-methoxybenzimidazole (5-OMeBza) were found to be efficiently incorporated as lower bases into norcobamides (NCbas). Structural analysis of the NCbas by nuclear magnetic resonance spectroscopy uncovered a regioselectivity in the utilization of these precursors for NCba biosynthesis. When 5-MeBza was added, a mixture of 5-MeBza-norcobamide and 6-MeBza-norcobamide was formed, and the PceA enzyme activity was affected. In the presence of 5-OHBza, almost exclusively 6-OHBza-norcobamide was produced, while in the presence of 5-OMeBza, predominantly 5-OMeBza-norcobamide was detected. Both NCbas were incorporated into PceA, and no negative effect on the PceA activity was observed. In crystal structures of PceA, both NCbas were bound in the base-off mode with the 6-OHBza and 5-OMeBza lower bases accommodated by the same solvent-exposed hydrophilic pocket that harbors the adenine as the lower base of authentic norpseudo-B12. In this study, a selective production of different norcobamide isomers containing singly substituted benzimidazoles as lower bases is shown, and unique structural insights into their utilization as cofactors by a cobamide-containing enzyme are provided.

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 Dates: 2018-01-292018
 Publication Status: Published online
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 Identifiers: Other: NMR254
DOI: 10.1128/JB.00584-17
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Title: Journal of Bacteriology
  Other : J. Bacteriol.
Source Genre: Journal
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Publ. Info: Washington, DC : American Society for Microbiology (ASM)
Pages: - Volume / Issue: 200 (8) Sequence Number: e00584-17 Start / End Page: - Identifier: ISSN: 0021-9193
CoNE: https://pure.mpg.de/cone/journals/resource/954925410823