NMR Analysis of Carboxylate Isotopomers of 13C-Metabolites by Chemoselective Derivatization with 15N-Cholamine

Sara Vicente-Muñoz, Penghui Lin, Teresa W.M. Fan, Andrew N. Lane

Research output: Contribution to journalArticlepeer-review

5 Scopus citations


A substantial fraction of common metabolites contains carboxyl functional groups. Their 13C isotopomer analysis by nuclear magnetic resonance (NMR) is hampered by the low sensitivity of the 13C nucleus, the slow longitudinal relaxation for the lack of an attached proton, and the relatively low chemical shift dispersion of carboxylates. Chemoselective (CS) derivatization is a means of tagging compounds in a complex mixture via a specific functional group. 15N1-cholamine has been shown to be a useful CS agent for carboxylates, producing a peptide bond that can be detected via 15N-attached H with high sensitivity in heteronuclear single quantum coherence experiments. Here, we report an improved method of derivatization and show how 13C-enrichment at the carboxylate and/or the adjacent carbon can be determined via one-and two-bond coupling of the carbons adjacent to the cholamine 15N atom in the derivatives. We have applied this method for the determination of 13C isotopomer distribution in the extracts of A549 cell culture and liver tissue from a patient-derived xenograft mouse.

Original languageEnglish
Pages (from-to)6629-6637
Number of pages9
JournalAnalytical Chemistry
Issue number17
StatePublished - May 4 2021

Bibliographical note

Funding Information:
This work was supported in part by the National Institutes of Health 5R01ES022191-04, 3R01ES022191-04S1, 1U24DK097215-01A1, P01 CA163223-01A1, and 1P20GM121327-01. We thank Dr. Timothy Scott for the mouse sample preparation and Yan Zhang for preparing the A549 cells.

Publisher Copyright:
© 2021 American Chemical Society.

ASJC Scopus subject areas

  • Analytical Chemistry


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