Journal article
Synthesis and Structure Reassignment of Malylglutamate, a Recently Discovered Earthworm Metabolite
Journal of natural products (Washington, D.C.), Vol.82(2), pp.417-421
02/22/2019
DOI: 10.1021/acs.jnatprod.8b01083
PMCID: PMC9040194
PMID: 30735390
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.
Details
- Title: Subtitle
- Synthesis and Structure Reassignment of Malylglutamate, a Recently Discovered Earthworm Metabolite
- Creators
- Corey M GriffithAbigail FeceuCynthia K LariveDavid B C Martin
- Resource Type
- Journal article
- Publication Details
- Journal of natural products (Washington, D.C.), Vol.82(2), pp.417-421
- DOI
- 10.1021/acs.jnatprod.8b01083
- PMID
- 30735390
- PMCID
- PMC9040194
- NLM abbreviation
- J Nat Prod
- ISSN
- 0163-3864
- eISSN
- 1520-6025
- Publisher
- United States
- Grant note
- DOI: 10.13039/100007602, name: University of California, Riverside
- Language
- English
- Date published
- 02/22/2019
- Academic Unit
- Iowa Neuroscience Institute; Chemistry
- Record Identifier
- 9984065856302771
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