Jeremiah Tipton - 2-Hydroxymethylboronate as a reagent to detect carbohydrates: application to the analysis of the formose reaction

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      Publication Details (including relevant citation   information):

      Ricardo, A.; Frye, F.; Carrigan, M.A.; Tipton,   J.D.; Powell, D.H.; Benner, S.A. The Journal of   Organic Chemistry 71(25), 9503-9505 (2006)

      Abstract:

      2-Hydroxymethylphenylboronate is described as a reagent that   converts neutral 1,2-diols, as found in simple carbohydrates,   into 1:1 anionic complexes that are easily detected by Fourier   transform ion cyclotron resonance mass spectrometry. The value of   this reagent was demonstrated through its application to analyze   complex mixtures of carbohydrates formed in the formose process,   often cited as a way that biologically significant carbohydrates   might have been generated from formaldehyde under prebiotic   conditions. Coupled with isotope studies, the reagent shows that   the simplest autocatalytic cycle for the consumption of   formaldehyde in this process cannot account for the bulk   consumption of formaldehyde

      Address (URL): http://pubs.acs.org/doi/abs/10.1021/jo061770h