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      Structural characterization of new microcystins containing tryptophan and oxidized tryptophan residues

      Puddick, Jonathan; Prinsep, Michèle R.; Wood, Susanna A.; Miles, Christopher O.; Rise, Frode; Cary, S. Craig; Hamilton, David P.; Wilkins, Alistair L.
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      Structural characterization.pdf
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      Structural characterization Supplementary.pdf
      Supplementary Materials , 739.2Kb
      DOI
       10.3390/md11083025
      Link
       www.mdpi.com
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      Puddick, J., Prinsep, M., Wood, S., Miles, C., Rise, F., Cary, S., Hamilton, D., et al. (2013). Structural characterization of new microcystins containing tryptophan and oxidized tryptophan residues. Marine Drugs, 11(8), 3025-3045.
      Permanent Research Commons link: https://hdl.handle.net/10289/8241
      Abstract
      Microcystins are cyclic peptides produced by cyanobacteria, which can be harmful to humans and animals when ingested. Eight of the (more than) 90 microcystin variants presently characterized, contain the amino acid tryptophan. The well-researched oxidation products of tryptophan; kynurenine, oxindolylalanine, and N-formylkynurenine, have been previously identified in intact polypeptides but microcystin congeners containing oxidized tryptophan moieties have not been reported. Liquid chromatography-tandem mass spectrometric analysis of an extract of Microcystis CAWBG11 led to the tentative identification of two new tryptophan-containing microcystins (MC‑WAba and MC-WL), as well as eight other microcystin analogs containing kynurenine, oxindolylalanine and N‑formylkynurenine (Nfk). Investigation of one of these congeners (MC‑NfkA) by nuclear magnetic resonance spectroscopy was used to verify the presence of Nfk in the microcystin. Liquid chromatography-mass spectrometry analysis of a tryptophan oxidation experiment demonstrated that tryptophan-containing microcystins could be converted into oxidized tryptophan analogs and that low levels of oxidized tryptophan congeners were present intracellularly in CAWBG11. MC-NfkR and MC-LNfk were detected in standards of MC-WR and MC-LW, indicating that care during storage of tryptophan-containing microcystins is required.
      Date
      2013
      Type
      Journal Article
      Publisher
      MDPI
      Rights
      ©2013 MDPI. This article is published under the Creative Commons Attribution License 3.0.
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      • Science and Engineering Papers [3019]
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