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β-Hydroxyaspartic acid in siderophores: biosynthesis and reactivity

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Abstract

A growing number of siderophores are found to contain β-hydroxyaspartic acid (β-OH-Asp) as a functional group for Fe(III) coordination, along with the more common catechol and hydroxamic acid groups. This review covers the structures, biosynthesis, and reactions of peptidic β-OH-Asp siderophores. Hydroxylation of Asp in siderophore biosynthesis is predicted to be carried out either through discrete aspartyl β-hydroxylating enzymes or through hydroxylating domains within non-ribosomal peptide synthetases, both of which display sequence homology to known non-heme iron(II), α-ketoglutarate-dependent dioxygenases. Ferric complexes of β-OH-Asp siderophores are photoreactive, resulting in reduction of Fe(III) and oxidative cleavage of the siderophore to yield distinct types of photoproducts. Probing the photoreactivity of synthetic Fe(III)-α-hydroxycarboxylate clusters yields mechanistic insights into the different photoproducts observed for β-OH-Asp and other α-hydroxycarboxylate siderophore Fe(III) complexes.

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Acknowledgements

We are grateful for support from NSF CHE-1710761.

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  1. Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA, 93106-9510, USA

    Clifford D. Hardy & Alison Butler

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Hardy, C.D., Butler, A. β-Hydroxyaspartic acid in siderophores: biosynthesis and reactivity. J Biol Inorg Chem 23, 957–967 (2018). https://doi.org/10.1007/s00775-018-1584-2

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