Universität zu Köln

Dieterich, Cora L., Probst, Silke, I, Ueoka, Reiko, Sandu, Ioana, Schaefle, Daniel, Dal Molin, Michael, Minas, Hannah A., Costa, Rodrigo, Oxenius, Annette, Sander, Peter ORCID: 0000-0003-1581-0682 and Piel, Joern (2022). Aquimarins, Peptide Antibiotics with Amino-Modified C-Termini from a Sponge-Derived Aquimarina sp. Bacterium. Angew. Chem.-Int. Edit., 61 (8). WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3773

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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/alpha-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 aquimarin residue as candidate building blocks for new peptidomimetic antibiotics.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Dieterich, Cora L. UNSPECIFIED UNSPECIFIED UNSPECIFIED Probst, Silke, I UNSPECIFIED UNSPECIFIED UNSPECIFIED Ueoka, Reiko UNSPECIFIED UNSPECIFIED UNSPECIFIED Sandu, Ioana UNSPECIFIED UNSPECIFIED UNSPECIFIED Schaefle, Daniel UNSPECIFIED UNSPECIFIED UNSPECIFIED Dal Molin, Michael UNSPECIFIED UNSPECIFIED UNSPECIFIED Minas, Hannah A. UNSPECIFIED UNSPECIFIED UNSPECIFIED Costa, Rodrigo UNSPECIFIED UNSPECIFIED UNSPECIFIED Oxenius, Annette UNSPECIFIED UNSPECIFIED UNSPECIFIED Sander, Peter UNSPECIFIED orcid.org/0000-0003-1581-0682 UNSPECIFIED Piel, Joern UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-593314
DOI:	10.1002/anie.202115802
Journal or Publication Title:	Angew. Chem.-Int. Edit.
Volume:	61
Number:	8
Date:	2022
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1521-3773
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language SOLID-PHASE SYNTHESIS; SP NOV.; LINKERS; DISEASE; ACIDS; IDENTIFICATION; BIOSYNTHESIS; RECOGNITION; MODEL; RESIN Multiple languages Chemistry, Multidisciplinary Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/59331