Further characterization of glycine-containing microcystins from the McMurdo Dry Valleys of Antarctica

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dc.contributor.authorPuddick, Jonathan
dc.contributor.authorPrinsep, Michèle R.
dc.contributor.authorWood, Susanna A.
dc.contributor.authorCary, S. Craig
dc.contributor.authorHamilton, David P.
dc.contributor.authorHolland, Patrick T.
dc.coverage.spatialSwitzerlanden_NZ
dc.date.accessioned2015-05-20T21:20:04Z
dc.date.available2015-02-10
dc.date.available2015-05-20T21:20:04Z
dc.date.issued2015-02-10
dc.description.abstractMicrocystins are hepatotoxic cyclic peptides produced by several cyanobacterial genera worldwide. In 2008, our research group identified eight new glycine-containing microcystin congeners in two hydro-terrestrial mat samples from the McMurdo Dry Valleys of Eastern Antarctica. During the present study, high-resolution mass spectrometry, amino acid analysis and micro-scale thiol derivatization were used to further elucidate their structures. The Antarctic microcystin congeners contained the rare substitution of the position-1 D-alanine for glycine, as well as the acetyl desmethyl modification of the position-5 Adda moiety (3S-amino-9S-methoxy-2S,6,8S-trimethyl-10-phenyldeca-4E,6E-dienoic acid). Amino acid analysis was used to determine the stereochemistry of several of the amino acids and conclusively demonstrated the presence of glycine in the microcystins. A recently developed thiol derivatization technique showed that each microcystin contained dehydrobutyrine in position-7 instead of the commonly observed N-methyl dehydroalanine.
dc.format.mimetypeapplication/pdf
dc.identifier.citationPuddick, J., Prinsep, M. R., Wood, S. A., Cary, S. C., Hamilton, D. P., & Holland, P. T. (2015). Further characterization of glycine-containing microcystins from the McMurdo Dry Valleys of Antarctica. Toxins, 7(2), 493–515. http://doi.org/10.3390/toxins7020493en
dc.identifier.doi10.3390/toxins7020493
dc.identifier.eissn2072-6651
dc.identifier.urihttps://hdl.handle.net/10289/9328
dc.language.isoen
dc.publisherMDPI AG
dc.relation.isPartOfToxins
dc.relation.urihttp://www.mdpi.com/2072-6651/7/2/493
dc.rights© 2015 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/4.0/).
dc.subjectamino acid analysis
dc.subjectAntarctica
dc.subjectmass spectrometry
dc.subjectmicrocystin
dc.subjectthiol derivatization
dc.titleFurther characterization of glycine-containing microcystins from the McMurdo Dry Valleys of Antarctica
dc.typeJournal Article
pubs.begin-page493
pubs.elements-id119259
pubs.end-page515
pubs.issue2
pubs.notesEvidence of peer review: http://www.mdpi.com/journal/toxins/about
pubs.organisational-group/Waikato
pubs.organisational-group/Waikato/FSEN
pubs.organisational-group/Waikato/FSEN/School of Science
pubs.volume7
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