Synthesis and Structure Reassignment of Malylglutamate,
a Recently Discovered Earthworm Metabolite
Posted on 2019-02-08 - 20:19
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.
CITE THIS COLLECTION
DataCite
3 Biotech
3D Printing in Medicine
3D Research
3D-Printed Materials and Systems
4OR
AAPG Bulletin
AAPS Open
AAPS PharmSciTech
Abhandlungen aus dem Mathematischen Seminar der Universität Hamburg
ABI Technik (German)
Academic Medicine
Academic Pediatrics
Academic Psychiatry
Academic Questions
Academy of Management Discoveries
Academy of Management Journal
Academy of Management Learning and Education
Academy of Management Perspectives
Academy of Management Proceedings
Academy of Management Review
Griffith, Corey
M.; Feceu, Abigail; Larive, Cynthia K.; B. C. Martin, David (2019). Synthesis and Structure Reassignment of Malylglutamate,
a Recently Discovered Earthworm Metabolite. ACS Publications. Collection. https://doi.org/10.1021/acs.jnatprod.8b01083
or
Select your citation style and then place your mouse over the citation text to select it.
SHARE
Usage metrics
Read the peer-reviewed publication
AUTHORS (4)
CG
Corey
M. Griffith
AF
Abigail Feceu
CL
Cynthia K. Larive
DB
David B. C. Martin