Bacicyclin, a new antibacterial cyclic hexapeptide from Bacillus sp. strain BC028 isolated from Mytilus edulis

[Display omitted] •A new cyclic hexapeptide (cyclo-(Gly-l-Leu-l-Val-l-IIe-d-Ala-d-Phe)) was detected.•Bacicyclin inhibits Gram-positive bacterial strains causing severe diseases.•Analogs of bacicyclin might be designed to increase antibiotic efficacy. A new cyclic hexapeptide, cyclo-(Gly-Leu-Val-IIe...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2018-02, Vol.28 (4), p.558-561
Hauptverfasser: Wiese, Jutta, Abdelmohsen, Usama Ramadan, Motiei, Asa, Humeida, Ute Hentschel, Imhoff, Johannes F.
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Sprache:eng
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Zusammenfassung:[Display omitted] •A new cyclic hexapeptide (cyclo-(Gly-l-Leu-l-Val-l-IIe-d-Ala-d-Phe)) was detected.•Bacicyclin inhibits Gram-positive bacterial strains causing severe diseases.•Analogs of bacicyclin might be designed to increase antibiotic efficacy. A new cyclic hexapeptide, cyclo-(Gly-Leu-Val-IIe-Ala-Phe), named bacicyclin (1), was isolated from a marine Bacillus sp. strain associated with Mytilus edulis. The sequences of the amino acid building blocks of the cyclic peptide and its structure were determined by 1D- and 2D-NMR techniques. Marfey’s analysis showed that the amino acid building blocks had L-configuration in all cases except for alanine and phenylalanine, which had D-configuration. Bacicyclin (1) exhibited antibacterial activity against the clinically relevant strains Enterococcus faecalis and Staphylococcus aureus with minimal inhibitory concentration values of 8 and 12 µM, respectively. These results demonstrate the potential of marine bacteria as a promising source for the discovery of new antibiotics.
ISSN:0960-894X
1464-3405
1464-3405
DOI:10.1016/j.bmcl.2018.01.062