| Condensation of the isoprenoid and amino precursors in the biosynthesis of domoic acid. | |
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MedLine Citation:
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PMID: 22041653 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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Understanding how environmental signals regulate production of domoic acid in blooms of Pseudo-nitzschia spp. at a molecular level requires description of the biochemical pathway to this kainoid neurotoxin. Precursor feeding studies have suggested domoic acid arises from the condensation of the C(10) isoprenoid geranyl diphosphate with glutamate, but the specific reactions leading to domoic acid from these precursors remain undescribed. Here, we develop a method to derivatize domoic acid with propyl chloroformate that enables gas chromatography-mass spectrometry (GC-MS) analysis to measure incorporation of stable isotopes into domoic acid generated in cultures incubated with isotopically-labeled substrates. We apply this method to demonstrate that both (2)H from [1-(2)H(2)]geraniol are incorporated into domoic acid, suggesting that the condensation of geranyl diphosphate with an amino group occurs by nucleophilic substitution of the diphosphate rather than by oxidation of geraniol to the aldehyde before reaction with an amino group to form an imine. Ultimately, these and similar studies will facilitate the identification of DA biosynthetic enzymes and genes which will enable the study of how environmental factors regulate DA biosynthesis at the molecular level. |
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Authors:
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Thomas J Savage; G Jason Smith; Amy T Clark; Portia N Saucedo |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-10-25 |
Journal Detail:
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Title: Toxicon : official journal of the International Society on Toxinology Volume: - ISSN: 1879-3150 ISO Abbreviation: - Publication Date: 2011 Oct |
Date Detail:
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Created Date: 2011-11-1 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 1307333 Medline TA: Toxicon Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Copyright Information:
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Copyright © 2011. Published by Elsevier Ltd. |
Affiliation:
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Department of Chemistry, California State University Sacramento, Sacramento, CA 95819, USA. |
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