The stability of D-glucose 1  in aqueous solution has attracted attention in recent years because of the potential role of spontaneous glucose autoxidation in promoting protein modification in vivo, especially in diabetic patients.  Aqueous solutions of 1  in phosphate buffer at pH 7.4, incubated at 37 �C and open to the atmosphere for several months, contain degradation products such as D-arabinose and glyoxal, both of which can cause protein covalent modification.  This behavior has important implications not only for studies of protein glycation, but also for biochemical studies where glucose solutions are part of the experimental protocol; aqueous solutions of 1 , incubated for moderately short periods of time at 37 �C, contain degradation products that could interfere with data interpretation.  Solution stability is also critical for pharmaceutical preparations where 1  is involved either as an API or an excipient.        The stability of 1  in phosphate buffer was examined by 13C NMR spectroscopy using a series of singly 13C-labeled D-glucoses as substrates:  D-[1-13C], [2-13C], [3-13C], [4-13C], [5-13C], and [6-13C]glucose.  This experimental approach allows determinations of the specific fates of individual carbons in 1  during degradation.  Contrary to prior findings, aqueous solutions of 1  contain mainly D-fructose after 2-3 months at 37 �C.  These solutions also contain additional rearrangement and degradation products that have been characterized.  Chemical mechanisms to explain the origins of these products have been proposed, and additional labeling experiments with 13C and 2H are underway to test these mechanisms.

On the stability of D-glucose in aqueous phosphate buffer: A <sup>13</sup>C NMR investigation with singly <sup>13</sup>C-labeled isotopomers

246th National Meeting (2013)

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On the stability of D-glucose in aqueous phosphate buffer: A 13C NMR investigation with singly 13C-labeled isotopomers

On the stability of D-glucose in aqueous phosphate buffer: A ¹³C NMR investigation with singly ¹³C-labeled isotopomers