2-Hydroxymethylboronate as a Reagent To Detect Carbohydrates: Application to the Analysis of the Formose Reaction

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• 作者：Alonso Ricardo ; Fabianne Frye ; Matthew A. Carrigan ; Jeremiah D. Tipton ; David H. Powell ; Steven A. Benner
• 刊名：Journal of Organic Chemistry
• 出版年：2006
• 出版时间：December 8, 2006
• 年：2006
• 卷：71
• 期：25
• 页码：9503 - 9505
• 全文大小：123K
• 年卷期：v.71,no.25(December 8, 2006)
• ISSN：1520-6904

文摘

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