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Biosynthetic route towards saxitoxin and shunt pathway
Saxitoxin, the most potent voltage-gated sodium channel blocker, is one of the paralytic shellfish toxins (PSTs) produced by cyanobacteria and dinoflagellates. Recently, putative biosynthetic genes of PSTs were reported in these microorganisms. We previously synthesized genetically predicted biosynt...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4740887/ https://www.ncbi.nlm.nih.gov/pubmed/26842222 http://dx.doi.org/10.1038/srep20340 |
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author | Tsuchiya, Shigeki Cho, Yuko Konoki, Keiichi Nagasawa, Kazuo Oshima, Yasukatsu Yotsu-Yamashita, Mari |
author_facet | Tsuchiya, Shigeki Cho, Yuko Konoki, Keiichi Nagasawa, Kazuo Oshima, Yasukatsu Yotsu-Yamashita, Mari |
author_sort | Tsuchiya, Shigeki |
collection | PubMed |
description | Saxitoxin, the most potent voltage-gated sodium channel blocker, is one of the paralytic shellfish toxins (PSTs) produced by cyanobacteria and dinoflagellates. Recently, putative biosynthetic genes of PSTs were reported in these microorganisms. We previously synthesized genetically predicted biosynthetic intermediates, Int-A’ and Int-C’2, and also Cyclic-C’ which was not predicted based on gene, and identified them all in the toxin-producing cyanobacterium Anabaena circinalis (TA04) and the dinoflagellate Alexandrium tamarense (Axat-2). This study examined the incorporation of (15)N-labeled intermediates into PSTs (C1 and C2) in A. circinalis (TA04). Conversions from Int-A’ to Int-C’2, from Int-C’2 to Cyclic-C’, and from Int-A’ and Int-C’2 to C1 and C2 were indicated using high resolution-LC/MS. However, Cyclic-C’ was not converted to C1 and C2 and was detected primarily in the extracellular medium. These results suggest that Int-A’ and Int-C’2 are genuine precursors of PSTs, but Int-C’2 converts partially to Cyclic-C’ which is a shunt product excreted to outside the cells. This paper provides the first direct demonstration of the biosynthetic route towards saxitoxin and a shunt pathway. |
format | Online Article Text |
id | pubmed-4740887 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Nature Publishing Group |
record_format | MEDLINE/PubMed |
spelling | pubmed-47408872016-02-09 Biosynthetic route towards saxitoxin and shunt pathway Tsuchiya, Shigeki Cho, Yuko Konoki, Keiichi Nagasawa, Kazuo Oshima, Yasukatsu Yotsu-Yamashita, Mari Sci Rep Article Saxitoxin, the most potent voltage-gated sodium channel blocker, is one of the paralytic shellfish toxins (PSTs) produced by cyanobacteria and dinoflagellates. Recently, putative biosynthetic genes of PSTs were reported in these microorganisms. We previously synthesized genetically predicted biosynthetic intermediates, Int-A’ and Int-C’2, and also Cyclic-C’ which was not predicted based on gene, and identified them all in the toxin-producing cyanobacterium Anabaena circinalis (TA04) and the dinoflagellate Alexandrium tamarense (Axat-2). This study examined the incorporation of (15)N-labeled intermediates into PSTs (C1 and C2) in A. circinalis (TA04). Conversions from Int-A’ to Int-C’2, from Int-C’2 to Cyclic-C’, and from Int-A’ and Int-C’2 to C1 and C2 were indicated using high resolution-LC/MS. However, Cyclic-C’ was not converted to C1 and C2 and was detected primarily in the extracellular medium. These results suggest that Int-A’ and Int-C’2 are genuine precursors of PSTs, but Int-C’2 converts partially to Cyclic-C’ which is a shunt product excreted to outside the cells. This paper provides the first direct demonstration of the biosynthetic route towards saxitoxin and a shunt pathway. Nature Publishing Group 2016-02-04 /pmc/articles/PMC4740887/ /pubmed/26842222 http://dx.doi.org/10.1038/srep20340 Text en Copyright © 2016, Macmillan Publishers Limited http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Article Tsuchiya, Shigeki Cho, Yuko Konoki, Keiichi Nagasawa, Kazuo Oshima, Yasukatsu Yotsu-Yamashita, Mari Biosynthetic route towards saxitoxin and shunt pathway |
title | Biosynthetic route towards saxitoxin and shunt pathway |
title_full | Biosynthetic route towards saxitoxin and shunt pathway |
title_fullStr | Biosynthetic route towards saxitoxin and shunt pathway |
title_full_unstemmed | Biosynthetic route towards saxitoxin and shunt pathway |
title_short | Biosynthetic route towards saxitoxin and shunt pathway |
title_sort | biosynthetic route towards saxitoxin and shunt pathway |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4740887/ https://www.ncbi.nlm.nih.gov/pubmed/26842222 http://dx.doi.org/10.1038/srep20340 |
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