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NMR Derivatives for Quantification of 2 H and 13 C‐Enrichment of Human Glucuronide from Metabolic Tracers

2006; Taylor & Francis; Volume: 25; Issue: 2-3 Linguagem: Inglês

10.1080/07328300600732840

1532-2327

John G. Jones, Cristina Barosa, Filipe Coreta‐Gomes, Ana C. Mendes, Teresa C. Delgado, Luísa Diogo, Paula Garcia, Margarida Bastos, Luísa Barros, Ana Fagulha, Carla Baptista, Manuela Carvalheiro, M. Madalena Caldeira,

Analytical Chemistry and Chromatography

Quantification of 2H and 13C enrichment distributions in human urinary glucuronide following ingestion of 2H2O and 13C gluconeogenic tracers was achieved by NMR spectroscopy of the 1,2‐O‐isopropylidene‐α‐D‐glucofuranurono‐6,3‐lactone and 5‐O‐acetyl‐1,2‐O‐isopropylidene‐α‐D‐glucofuranurono‐6,3‐lactone derivatives. The derivatization process is simple and can be applied to any glucuronide species. The derivatives are highly soluble in acetonitrile and generate well‐resolved and narrow 2H and 13C NMR signals. The 1,2‐O‐isopropylidene‐α‐D‐glucofuranurono‐6,3‐lactone derivative provided resolution of the six glucuronide 13C signals and numerous 13C isotopomer populations through one‐ and two‐bond 13C‐13C‐coupling, while the 5‐O‐acetyl‐1,2‐O‐isopropylidene‐α‐D‐glucofuranurono‐6,3‐lactone derivative provided complete resolution of the 2H NMR signals for the five glucuronide hydrogens. The isopropylidene methyl signals were also resolved and provided an internal 2H enrichment standard following the acetonation of glucuronolactone with deuterated acetone.