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Sequencing of cyclic peptides by NMR and MS techniques demonstrated on stylissamides A–F

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Abstract

The Caribbean sponge Stylissa caribica is the source of a series of six proline-rich cyclic heptapeptides, the stylissamides A–F (1–6). Here, we review the elucidation of the structures of 1–6 by a combination of NMR and mass spectrometry (MS/MS and MSn experiments). A detailed description of the NMR analysis (including semi-selective 1H,13C-HMBC and NOESY experiments) for sequencing the peptides is provided for stylissamides A (1) and E (5).

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Acknowledgments

Financial support from the Deutsche Forschungsgemeinschaft (DFG) (Ko 1314/5-1 and 5-2, DFG-Forschergruppe FOR 934) is gratefully acknowledged. Sponge collection was carried out by Dr. M. Assmann during a scientific expedition to the Bahamas in 2000. During this time the project was also sponsored by the DFG (Ko 1314/3-1 to 3-4). We would like to acknowledge the support of Prof. Dr. J. R. Pawlik (University of North Carolina, Wilmington, USA) who gave members of the Köck research group the opportunity to participate in scientific sojourns to the Bahamas (1998 to 2008).

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  1. Alfred‐Wegener‐Institut, Helmholtz‐Zentrum für Polar- und Meeresforschung, Am Handelshafen 12, 27570, Bremerhaven, Germany

    Christine Cychon, Gesine Schmidt & Matthias Köck

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  1. Christine Cychon
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  2. Gesine Schmidt
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  3. Matthias Köck
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Correspondence to Matthias Köck.

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Cychon, C., Schmidt, G. & Köck, M. Sequencing of cyclic peptides by NMR and MS techniques demonstrated on stylissamides A–F. Phytochem Rev 12, 495–505 (2013). https://doi.org/10.1007/s11101-012-9252-6

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  • DOI: https://doi.org/10.1007/s11101-012-9252-6

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