Further Characterization of Glycine-Containing Microcystins from the McMurdo Dry Valleys of Antarctica
Microcystins 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 stud...
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ftpubmed:oai:pubmedcentral.nih.gov:4344637 2023-05-15T14:05:12+02:00 Further Characterization of Glycine-Containing Microcystins from the McMurdo Dry Valleys of Antarctica Puddick, Jonathan Prinsep, Michèle R. Wood, Susanna A. Cary, Stephen Craig Hamilton, David P. Holland, Patrick T. 2015-02-10 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4344637 http://www.ncbi.nlm.nih.gov/pubmed/25675414 https://doi.org/10.3390/toxins7020493 en eng MDPI http://www.ncbi.nlm.nih.gov/pmc/articles/PMC http://www.ncbi.nlm.nih.gov/pubmed/25675414 http://dx.doi.org/10.3390/toxins7020493 © 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/). CC-BY Article Text 2015 ftpubmed https://doi.org/10.3390/toxins7020493 2015-03-22T00:58:38Z Microcystins 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. Text Antarc* Antarctic Antarctica McMurdo Dry Valleys PubMed Central (PMC) Antarctic McMurdo Dry Valleys The Antarctic Toxins 7 2 493 515 |
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Article Puddick, Jonathan Prinsep, Michèle R. Wood, Susanna A. Cary, Stephen Craig Hamilton, David P. Holland, Patrick T. Further Characterization of Glycine-Containing Microcystins from the McMurdo Dry Valleys of Antarctica |
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description |
Microcystins 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. |
format |
Text |
author |
Puddick, Jonathan Prinsep, Michèle R. Wood, Susanna A. Cary, Stephen Craig Hamilton, David P. Holland, Patrick T. |
author_facet |
Puddick, Jonathan Prinsep, Michèle R. Wood, Susanna A. Cary, Stephen Craig Hamilton, David P. Holland, Patrick T. |
author_sort |
Puddick, Jonathan |
title |
Further Characterization of Glycine-Containing Microcystins from the McMurdo Dry Valleys of Antarctica |
title_short |
Further Characterization of Glycine-Containing Microcystins from the McMurdo Dry Valleys of Antarctica |
title_full |
Further Characterization of Glycine-Containing Microcystins from the McMurdo Dry Valleys of Antarctica |
title_fullStr |
Further Characterization of Glycine-Containing Microcystins from the McMurdo Dry Valleys of Antarctica |
title_full_unstemmed |
Further Characterization of Glycine-Containing Microcystins from the McMurdo Dry Valleys of Antarctica |
title_sort |
further characterization of glycine-containing microcystins from the mcmurdo dry valleys of antarctica |
publisher |
MDPI |
publishDate |
2015 |
url |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4344637 http://www.ncbi.nlm.nih.gov/pubmed/25675414 https://doi.org/10.3390/toxins7020493 |
geographic |
Antarctic McMurdo Dry Valleys The Antarctic |
geographic_facet |
Antarctic McMurdo Dry Valleys The Antarctic |
genre |
Antarc* Antarctic Antarctica McMurdo Dry Valleys |
genre_facet |
Antarc* Antarctic Antarctica McMurdo Dry Valleys |
op_relation |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC http://www.ncbi.nlm.nih.gov/pubmed/25675414 http://dx.doi.org/10.3390/toxins7020493 |
op_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/). |
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CC-BY |
op_doi |
https://doi.org/10.3390/toxins7020493 |
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Toxins |
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7 |
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493 |
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515 |
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1766276928385318912 |