IngentaConnect NMR Derivatives for Quantification of 2 H and 13 CEnrichment of H...

Authors: Jones, John¹; Barosa, Cristina¹; Gomes, Filipe²; Carina Mendes, Ana²; Delgado, Teresa¹; Diogo, Luisa³; Garcia, Paula³; Bastos, Margarida⁴; Barros, Luisa⁴; Fagulha, Ana⁴; Baptista, Carla⁴; Carvalheiro, Manuela⁴; Madalena Caldeira, M.²

Source: Journal of Carbohydrate Chemistry, Volume 25, Numbers 2-3, -3/March-April 2006 , pp. 203-217(15)

Publisher: Taylor and Francis Ltd

Abstract:

Quantification of 2 H and 13 C enrichment distributions in human urinary glucuronide following ingestion of 2 H 2 O and 13 C 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 2 H and 13 C NMR signals. The 1,2‐ O ‐isopropylidene‐α‐D‐glucofuranurono‐6,3‐lactone derivative provided resolution of the six glucuronide 13 C signals and numerous 13 C isotopomer populations through one‐ and two‐bond 13 C‐ 13 C‐coupling, while the 5‐ O ‐acetyl‐1,2‐ O ‐isopropylidene‐α‐D‐glucofuranurono‐6,3‐lactone derivative provided complete resolution of the 2 H NMR signals for the five glucuronide hydrogens. The isopropylidene methyl signals were also resolved and provided an internal 2 H enrichment standard following the acetonation of glucuronolactone with deuterated acetone.

Keywords: Isotopomers; Gluconeogenesis; Intermediary metabolism; Glycogen; Liver

Document Type: Research article

DOI: 10.1080/07328300600732840

Affiliations: 1: NMR Research Unit, Department of Biochemistry and Center for Neurosciences and Cell Biology, University of Coimbra, Coimbra, Portugal 2: Department of Chemistry, University of Coimbra, Coimbra, Portugal 3: Pediatrics Hospital of Coimbra, Coimbra, Portugal 4: Department of Endocrinology, University Hospital of Coimbra, Coimbra, Portugal

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