Show simple item record  

dc.contributor.authorPuddick, Jonathan
dc.contributor.authorPrinsep, Michèle R.
dc.contributor.authorWood, Susanna A.
dc.contributor.authorMiles, Christopher O.
dc.contributor.authorRise, Frode
dc.contributor.authorCary, S. Craig
dc.contributor.authorHamilton, David P.
dc.contributor.authorWilkins, Alistair L.
dc.coverage.spatialSwitzerlanden_NZ
dc.date.accessioned2013-11-26T22:48:21Z
dc.date.available2013-11-26T22:48:21Z
dc.date.copyright2013-08-21
dc.date.issued2013
dc.identifier.citationPuddick, 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.en_NZ
dc.identifier.urihttps://hdl.handle.net/10289/8241
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.en_NZ
dc.format.mimetypeapplication/pdf
dc.format.mimetypeapplication/pdf
dc.language.isoenen_NZ
dc.publisherMDPIen_NZ
dc.relation.ispartofMarine Drugs
dc.relation.urihttp://www.mdpi.com/1660-3397/11/8/3025en_NZ
dc.rights©2013 MDPI. This article is published under the Creative Commons Attribution License 3.0.en_NZ
dc.subjectmicrocystinen_NZ
dc.subjectmicrocystinen_NZ
dc.subjectN‑formylkynurenineen_NZ
dc.subjectmass spectrometryen_NZ
dc.subjectnuclear magnetic resonance spectroscopyen_NZ
dc.subjectMicrocystis CAWBG11en_NZ
dc.titleStructural characterization of new microcystins containing tryptophan and oxidized tryptophan residuesen_NZ
dc.typeJournal Articleen_NZ
dc.identifier.doi10.3390/md11083025en_NZ
dc.relation.isPartOfMarine Drugsen_NZ
pubs.begin-page3025en_NZ
pubs.elements-id38812
pubs.end-page3045en_NZ
pubs.issue8en_NZ
pubs.volume11en_NZ


Files in this item

This item appears in the following Collection(s)

Show simple item record