10.1021/acs.jnatprod.8b01083.s001
Corey
M. Griffith
Corey
M.
Griffith
Abigail Feceu
Abigail
Feceu
Cynthia K. Larive
Cynthia K.
Larive
David B. C. Martin
David
B. C. Martin
Synthesis and Structure Reassignment of Malylglutamate,
a Recently Discovered Earthworm Metabolite
American Chemical Society
2019
sample
HMBC
Earthworm Metabolite Malylglutamate
diastereomer
NMR spectra
2019-02-08 20:19:22
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Synthesis_and_Structure_Reassignment_of_Malylglutamate_a_Recently_Discovered_Earthworm_Metabolite/7697942
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 (<b>1</b>) 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 (<b>2</b>) diastereomers were synthesized, L,L-<b>2</b> and
D,D-<b>2</b>. NMR spectra were an excellent match with the natural
sample, and chiral-phase chromatography was employed to identify (−)-β-l-malyl-l-glutamate (<b>2</b>) as the isomer
native to <i>Eisenia fetida</i>.