TY - JOUR
T1 - Synthesis and structure reassignment of malylglutamate, a recently discovered earthworm metabolite
AU - Griffith, Corey M.
AU - Feceu, Abigail
AU - Larive, Cynthia K.
AU - Martin, David B.C.
N1 - Publisher Copyright:
© 2019 American Chemical Society and American Society of Pharmacognosy.
PY - 2019/2/22
Y1 - 2019/2/22
N2 - 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 (â)-β-l-malyl-l-glutamate (2) as the isomer native to Eisenia fetida.
AB - 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 (â)-β-l-malyl-l-glutamate (2) as the isomer native to Eisenia fetida.
UR - http://www.scopus.com/inward/record.url?scp=85061524539&partnerID=8YFLogxK
U2 - 10.1021/acs.jnatprod.8b01083
DO - 10.1021/acs.jnatprod.8b01083
M3 - Article
C2 - 30735390
AN - SCOPUS:85061524539
SN - 0163-3864
VL - 82
SP - 417
EP - 421
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 2
ER -