Aquimarins, Peptide Antibiotics with Amino-Modified C-Termini from a Sponge-Derived Aquimarina sp. Bacterium
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Date
2022-02-14
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Journal Article
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yes
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Abstract
Genome mining and bioactivity studies suggested the sponge-derived bacterium Aquimarina sp. Aq135 as a producer of new antibiotics. Activity-guided isolation identified antibacterial peptides, named aquimarins, featuring a new scaffold with an unusual C-terminal amino group and chlorine moieties. Responsible for the halogenation is the Fe(II)/α-ketoglutarate-dependent chlorinase AqmA that halogenates up to two isoleucine residues in a carrier protein-dependent fashion. Total syntheses of two natural aquimarins and eight non-natural variants were developed. Structure-activity relationship (SAR) studies with these compounds showed that the synthetically more laborious chlorinations are not required for antibacterial activity but enhance cytotoxicity. In contrast, variants lacking the C-terminal amine were virtually inactive, suggesting diamines similar to the terminal aquimarine residue as candidate building blocks for new peptidomimetic antibiotics.
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published
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Journal / series
Volume
61 (8)
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Publisher
Wiley-VCH
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Subject
Antibiotics; Bacteria; Natural products; Nonribosomal peptides; Sponges
Organisational unit
03980 - Piel, Jörn / Piel, Jörn
03625 - Oxenius, Annette / Oxenius, Annette