ArticleJournal of natural products2019
Synthesis and Structure Reassignment of Malylglutamate, a Recently Discovered Earthworm Metabolite.
Article in Journal of natural products, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
1 citing paper in PubMed.
- Metabolite biomarkers of chlorothalonil exposure in earthworms, coelomic fluid, and coelomocytes.The Science of the total environment · 2019Article
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Authors and funding
4 authors.
Funding
Abstract
Malylglutamate, a newly identified metabolite in earthworms, was synthesized using a traditional peptide coupling approach for assembling the amide from protected malate and glutamate precursors. The proposed structure (1) and a diastereomer were synthesized, but their NMR spectra did not match the natural sample. Further analysis of the natural sample using HMBC spectroscopy suggested an alternative attachment of the malyl moiety, and β-malylglutamate (2) diastereomers were synthesized, L,L-2 and D,D-2. NMR spectra were an excellent match with the natural sample, and chiral-phase chromatography was employed to identify (-)-β-l-malyl-l-glutamate (2) as the isomer native to Eisenia fetida.
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