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Structural Requirements for Ga³⁺ Coordination in Synthetic Analogues of the Siderophore Piscibactin Deduced by Chemical Synthesis and Density Functional Theory Calculations.

ABSTRACT: Stereoselective total synthesis of several analogues of piscibactin (Pcb), the siderophore produced by different pathogenic Gram-negative bacteria, was performed. The acid-sensitive α-methylthiazoline 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 Ga³⁺ as a mimic of Fe³⁺ showed that the configuration of the hydroxyl group at C-13 as 13S is crucial for the chelation of Ga³⁺ to preserve the metal coordination, while the presence of a thiazole ring instead of the α-methylthiazoline moiety does not affect such coordination. A complete ¹H and ¹³C NMR chemical shift assignment of the diaster

SUBMITTER: de la Fuente MC

PROVIDER: S-EPMC10189737 | biostudies-literature | 2023 May

REPOSITORIES: biostudies-literature

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Structural Requirements for Ga³⁺ Coordination in Synthetic Analogues of the Siderophore Piscibactin Deduced by Chemical Synthesis and Density Functional Theory Calculations.

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Structural Requirements for Ga3+ Coordination in Synthetic Analogues of the Siderophore Piscibactin Deduced by Chemical Synthesis and Density Functional Theory Calculations.

OmicsDI is part of the ELIXIR infrastructure

Tweets

Structural Requirements for Ga³⁺ Coordination in Synthetic Analogues of the Siderophore Piscibactin Deduced by Chemical Synthesis and Density Functional Theory Calculations.