Champacyclin, a New Cyclic Octapeptide from Streptomyces Strain C42 Isolated from the Baltic Sea.

Pesic, Alexander, Baumann, Heike Irmgard, Kleinschmidt, Katrin, Ensle, Paul, Wiese, Jutta , Süssmuth, Roderich and Imhoff, Johannes F. (2013) Champacyclin, a New Cyclic Octapeptide from Streptomyces Strain C42 Isolated from the Baltic Sea. Open Access Marine Drugs, 11 (12). pp. 4834-4857. DOI 10.3390/md11124834.

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Abstract

New isolates of Streptomyces champavatii were isolated from marine sediments of the Gotland Deep (Baltic Sea), from the Urania Basin (Eastern Mediterranean), and from the Kiel Bight (Baltic Sea). The isolates produced several oligopeptidic secondary metabolites, including the new octapeptide champacyclin (1a) present in all three strains. Herein, we report on the isolation, structure elucidation and determination of the absolute stereochemistry of this isoleucine/leucine (Ile/Leu = Xle) rich cyclic octapeptide champacyclin (1a). As 2D nuclear magnetic resonance (NMR) spectroscopy could not fully resolve the structure of (1a), additional information on sequence and configuration of stereocenters were obtained by a combination of multi stage mass spectrometry (MSn) studies, amino acid analysis, partial hydrolysis and subsequent enantiomer analytics with gas chromatography positive chmical ionization/electron impact mass spectrometry (GC-PCI/EI-MS) supported by comparison to reference dipeptides. Proof of the head-to-tail cyclization of (1a) was accomplished by solid phase peptide synthesis (SPPS) compared to an alternatively side chain cyclized derivative (2). Champacyclin (1a) is likely synthesized by a non-ribosomal peptide synthetase (NRPS), because of its high content of (d)-amino acids. The compound (1a) showed antimicrobial activity against the phytopathogen Erwinia amylovora causing the fire blight disease of certain plants.

Document Type: Article
Additional Information: WOS:000330220400010
Keywords: Streptomyces champavatii; antimicrobial activity; fire blight; cyclic peptides; sequence ladder analysis; chiral GC-PCI/EI-MS; ESI-Ion-Trap-MSn; solid phase peptide synthesis (SPPS); on-resin cyclization; 2D NMR
Research affiliation: OceanRep > GEOMAR > FB3 Marine Ecology > FB3-MI Marine Microbiology
Refereed: Yes
Open Access Journal?: Yes
DOI etc.: 10.3390/md11124834
ISSN: 1660-3397
Projects: BIOKATALYSE 2021, Future Ocean
Date Deposited: 10 Dec 2013 10:52
Last Modified: 02 Mar 2018 12:51
URI: http://oceanrep.geomar.de/id/eprint/22573

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