Calcaripeptides A–C, Cyclodepsipeptides from aCalcarisporiumStrain

Silber, Johanna, Ohlendorf, Birgit, Labes, Antje, Näther, Christian and Imhoff, Johannes F. (2013) Calcaripeptides A–C, Cyclodepsipeptides from aCalcarisporiumStrain Journal of Natural Products, 76 (8). pp. 1461-1467. DOI 10.1021/np400262t.

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Supplementary data:

Abstract

The isolation and structure elucidation of the novel calcaripeptides A (1), B (2), and C (3) and studies on their biosynthetic origin are described. The calcaripeptides were identified from Calcarisporium sp. strain KF525, which was isolated from the German Wadden Sea. Compounds 1–3 are macrocyclic structures composed of a proline and a phenylalanine residue as well as a nonpeptidic substructure. Structure elucidation was achieved by applying one- and two-dimensional NMR spectroscopy supported by high-resolution mass spectrometry. X-ray crystallography was performed to determine the relative configuration of 1. The absolute configuration of 1 was assigned by HPLC of the amino acids after hydrolysis of the molecule and derivatization with chiral agents. Studies on the biosynthesis by feeding 13C-labeled substrates revealed that the nonpeptidic part of 1 originates from acetate and l-methionine. The involvement of a hybrid between a polyketide synthase and a nonribosomal peptide synthetase in the biosynthesis of the calcaripeptides is discussed.

Document Type: Article
Additional Information: WOS:000323630500010
Research affiliation: OceanRep > The Future Ocean - Cluster of Excellence
OceanRep > GEOMAR > FB3 Marine Ecology > FB3-MI Marine Microbiology
OceanRep > GEOMAR > Applied R&D > Centre for Marine Substances (KiWiZ)
Refereed: Yes
DOI etc.: 10.1021/np400262t
ISSN: 0163-3864
Projects: Future Ocean, Marine Fungi
Date Deposited: 19 Sep 2013 09:24
Last Modified: 12 Jan 2015 12:16
URI: http://eprints.uni-kiel.de/id/eprint/21997

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