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dc.contributor.authorPuddick, Jonathan
dc.contributor.authorPrinsep, Michele R
dc.contributor.authorWood, Susanna A
dc.contributor.authorMiles, Christopher O
dc.contributor.authorRise, Frode
dc.contributor.authorCary, Stephen Craig
dc.contributor.authorHamilton, David P
dc.contributor.authorWilkins, Alistair L
dc.date.accessioned2017-05-18T00:57:03Z
dc.date.available2017-05-18T00:57:03Z
dc.date.issued2013
dc.identifier.issn1660-3397
dc.identifier.doi10.3390/md11083025
dc.identifier.urihttp://hdl.handle.net/10072/337282
dc.description.abstractMicrocystins 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.
dc.description.peerreviewedYes
dc.languageEnglish
dc.publisherM D P I AG
dc.relation.ispartofpagefrom3025
dc.relation.ispartofpageto3045
dc.relation.ispartofissue8
dc.relation.ispartofjournalMarine Drugs
dc.relation.ispartofvolume11
dc.subject.fieldofresearchPharmacology and Pharmaceutical Sciences not elsewhere classified
dc.subject.fieldofresearchPhysical Chemistry (incl. Structural)
dc.subject.fieldofresearchPharmacology and Pharmaceutical Sciences
dc.subject.fieldofresearchcode111599
dc.subject.fieldofresearchcode0306
dc.subject.fieldofresearchcode1115
dc.titleStructural characterization of new microcystins containing tryptophan and oxidized tryptophan residues
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
dcterms.licensehttp://creativecommons.org/licenses/by/3.0/
gro.rights.copyright© 2013 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
gro.hasfulltextFull Text
gro.griffith.authorHamilton, David P.


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