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Structural Requirements for Ga Coordination in Synthetic Analogues of the Siderophore Piscibactin Deduced by Chemical Synthesis and Density Functional Theory Calculations. | LitMetric

AI Article Synopsis

  • - The study focused on creating analogues of piscibactin (Pcb), a siderophore used by pathogenic Gram-negative bacteria, by replacing an unstable part of the molecule with a more stable thiazole ring, while analyzing the importance of hydroxyl configuration at C-13 for its ability to bind gallium (Ga).
  • - Researchers found that the configuration of the hydroxyl group at C-13 is essential for effective metal coordination, while the thiazole ring did not influence this process. They also used NMR and density functional theory to confirm the molecular structure and bonding capabilities of the Ga complexes formed.
  • - The Pcb Ga complexes showed no antimicrobial activity, aligning with the siderophore's role in

Article Abstract

Stereoselective total synthesis of several analogues of piscibactin (Pcb), the siderophore produced by different pathogenic Gram-negative bacteria, was performed. The acid-sensitive αmethylthiazoline moiety was replaced by a more stable thiazole ring, differing in the configuration of the OH group at the C-13 position. The ability of these Pcb analogues to form complexes with Ga as a mimic of Fe showed that the configuration of the hydroxyl group at C-13 as 13 is crucial for the chelation of Ga to preserve the metal coordination, while the presence of a thiazole ring instead of the αmethylthiazoline moiety does not affect such coordination. A complete H and C NMR chemical shift assignment of the diastereoisomer mixtures around C9/C10 was done for diagnostic stereochemical disposition. Additionally, density functional theory calculations were performed not only for confirming the stereochemistry of the Ga complex among the six possible diastereoisomers but also for deducing the ability of these to form octahedral coordination spheres with gallium. Finally, the lack of antimicrobial activity of Pcb and Pcb thiazole analogue Ga complexes against agrees with one of the roles of siderophores in protecting pathogens from metal ion toxicity. The efficient metal coordination shown by this scaffold suggests its possible use as a starting point for the design of new chelating agents or vectors for the development of new antibacterials that exploit the "Trojan horse" strategy using the microbial iron uptake mechanisms. The results obtained will be of great help in the development of biotechnological applications for these types of compounds.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10189737PMC
http://dx.doi.org/10.1021/acs.inorgchem.3c00787DOI Listing

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