2-Hydroxymethylboronate as a reagent to detect carbohydrates: application to the analysis of the formose reaction.
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.
Ricardo
Alonso
A
Departamento de Química, Universidad de los Andes, Bogota, Colombia. aricardo@molbio.mgh.harvard.edu
Frye
Fabianne
F
Carrigan
Matthew A
MA
Tipton
Jeremiah D
JD
Powell
David H
DH
Benner
Steven A
SA
D001896:Boron Compounds / Q000737:chemistry*; D002241:Carbohydrates / Q000032:analysis*; D007202:Indicators and Reagents / Q000737:chemistry*; D013058:Mass Spectrometry; D017550:Spectroscopy, Fourier Transform Infrared
C522872:2-hydroxymethylboronate; D001896:Boron Compounds; D002241:Carbohydrates; D007202:Indicators and Reagents