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Very high isotope incorporation in the C‐1 position of glucose by exchange with deuterium or tritium gas
Author(s) -
Long Mervyn A.,
Morimoto Hiromi,
Williams Philip G.
Publication year - 1995
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580361104
Subject(s) - tritium , chemistry , deuterium , tritium illumination , catalysis , radiochemistry , aqueous solution , kinetic isotope effect , isotope , solvent , hydrogen–deuterium exchange , heavy water , hydrogen , inorganic chemistry , nuclear chemistry , organic chemistry , nuclear physics , physics
The experimental conditions which control the exchange from deuterium or tritium gas into the C‐1 proton position of glucose in aqueous solution have been studied in detail, with a view to determining the factors which maximize exchange into glucose, but minimize exchange into the solvent water. The favoured conditions for producing glucose with close to 100% isotope labelling in the C‐1 position, and with negligible formation of labelled byproducts, were a reaction time of 6 to 8 hours, a temperature of 60 °C, and a pH of 7 or higher. Pd/BaSO 4 was the preferred catalyst and slow pre‐addition of the deuterium or tritium gas to the catalyst bed was essential to maximize the subsequent isotope exchange into the substrate.