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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ftmdpi:oai:mdpi.com:/2072-6651/7/2/493/ 2023-08-20T04:01:26+02:00 Further Characterization of Glycine-Containing Microcystins from the McMurdo Dry Valleys of Antarctica Jonathan Puddick Michèle Prinsep Susanna Wood Stephen Cary David Hamilton Patrick Holland agris 2015-02-10 application/pdf https://doi.org/10.3390/toxins7020493 EN eng Multidisciplinary Digital Publishing Institute Marine and Freshwater Toxins https://dx.doi.org/10.3390/toxins7020493 https://creativecommons.org/licenses/by/4.0/ Toxins; Volume 7; Issue 2; Pages: 493-515 microcystin Antarctica amino acid analysis mass spectrometry thiol derivatization Text 2015 ftmdpi https://doi.org/10.3390/toxins7020493 2023-07-31T20:41:49Z 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 ᴅ-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 MDPI Open Access Publishing Antarctic McMurdo Dry Valleys The Antarctic Toxins 7 2 493 515 |
institution |
Open Polar |
collection |
MDPI Open Access Publishing |
op_collection_id |
ftmdpi |
language |
English |
topic |
microcystin Antarctica amino acid analysis mass spectrometry thiol derivatization |
spellingShingle |
microcystin Antarctica amino acid analysis mass spectrometry thiol derivatization Jonathan Puddick Michèle Prinsep Susanna Wood Stephen Cary David Hamilton Patrick Holland Further Characterization of Glycine-Containing Microcystins from the McMurdo Dry Valleys of Antarctica |
topic_facet |
microcystin Antarctica amino acid analysis mass spectrometry thiol derivatization |
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 ᴅ-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 |
Jonathan Puddick Michèle Prinsep Susanna Wood Stephen Cary David Hamilton Patrick Holland |
author_facet |
Jonathan Puddick Michèle Prinsep Susanna Wood Stephen Cary David Hamilton Patrick Holland |
author_sort |
Jonathan Puddick |
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 |
Multidisciplinary Digital Publishing Institute |
publishDate |
2015 |
url |
https://doi.org/10.3390/toxins7020493 |
op_coverage |
agris |
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_source |
Toxins; Volume 7; Issue 2; Pages: 493-515 |
op_relation |
Marine and Freshwater Toxins https://dx.doi.org/10.3390/toxins7020493 |
op_rights |
https://creativecommons.org/licenses/by/4.0/ |
op_doi |
https://doi.org/10.3390/toxins7020493 |
container_title |
Toxins |
container_volume |
7 |
container_issue |
2 |
container_start_page |
493 |
op_container_end_page |
515 |
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1774724716282511360 |