A Novel Coenzyme A Analogue in the Anaerobic, Sulfate‐Reducing, Marine Bacterium Desulfobacula toluolica Tol2T. (8th December 2022)

• Record Type: Journal Article
• Authors: Bruns, Stefan; Cakić, Nevenka; Mitschke, Nico; Kopke, Bernd Johann; Rabus, Ralf; Wilkes, Heinz
• Is Part Of: Chembiochem. Volume 24:Number 2(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-12-08
• Subjects: anaerobic degradation -- Desulfobacula toluolica Tol2T -- inosino-CoA -- mass spectrometry -- metabolomics -- NMR spectroscopy; Biochemistry -- Periodicals; Molecular biology -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1002/cbic.202200584
• Languages: English
• ISSNs: 1439-4227

Abstract

Abstract: Coenzyme A (CoA) thioesters are formed during anabolic and catabolic reactions in every organism. Degradation pathways of growth‐supporting substrates in bacteria can be predicted by differential proteogenomic studies. Direct detection of proposed metabolites such as CoA thioesters by high‐performance liquid chromatography coupled with high‐resolution mass spectrometry can confirm the reaction sequence and demonstrate the activity of these degradation pathways. In the metabolomes of the anaerobic sulfate‐reducing bacterium Desulfobacula toluolica Tol2 T grown with different substrates various CoA thioesters, derived from amino acid, fatty acid or alcohol metabolism, have been detected. Additionally, the cell extracts of this bacterium revealed a number of CoA analogues with molecular masses increased by 1 dalton. By comparing the chromatographic and mass spectrometric properties of synthetic reference standards with those of compounds detected in cell extracts of D. toluolica Tol2 T and by performing co‐injection experiments, these analogues were identified as inosino‐CoAs. These CoA thioesters contain inosine instead of adenosine as the nucleoside. To the best of our knowledge, this finding represents the first detection of naturally occurring inosino‐CoA analogues. Abstract : Inosino‐coenzyme A, an analogue of the essential coenzyme A, was identified in cell extracts of the sulfate‐reducing marine bacterium Desulfobacula toluolica Tol2 T grown with different substrates under anoxic conditions. HPLC‐HRMS and NMR spectroscopy of synthetic standard compounds and bacterial cell extracts proved the identity of inosino‐coenzyme A, which contains inosine instead of adenosine as the nucleoside.