Skip Navigation
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

National Institute of Environmental Health Sciences

Use this QR code to view the newest version of this document
Use this QR code to view the newest version of this document

Your Environment. Your Health.

Publication Detail

Title: Synthesis and Structure Reassignment of Malylglutamate, a Recently Discovered Earthworm Metabolite.

Authors: Griffith, Corey M; Feceu, Abigail; Larive, Cynthia K; Martin, David B C

Published In J Nat Prod, (2019 Feb 22)

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.

PubMed ID: 30735390 Exiting the NIEHS site

MeSH Terms: Animals; Glutamates/chemical synthesis*; Glutamates/chemistry*; Glutamates/metabolism; Magnetic Resonance Spectroscopy; Malates/chemistry; Oligochaeta/metabolism*; Peptides/chemical synthesis*; Peptides/chemistry; Stereoisomerism

Back
to Top