N-(1-Deoxy-d -fructos-1-yl) Fumonisin B1, the Initial Reaction Product of Fumonisin B1 and d -Glucose
| Autor: | Ronald D. Plattner, David Weisleder, Stephen M. Poling |
|---|---|
| Rok vydání: | 2002 |
| Předmět: |
chemistry.chemical_classification
Fumonisin B1 Molecular Structure Carboxylic Acids food and beverages General Chemistry Mycotoxins Spectrometry Mass Fast Atom Bombardment Alkaline hydrolysis (body disposal) Fumonisins Aldehyde Mass Spectrometry chemistry.chemical_compound Hydrolysis Glucose chemistry D-Glucose Amadori rearrangement Fumonisin Organic chemistry Indicators and Reagents Amine gas treating General Agricultural and Biological Sciences Chromatography Liquid Nuclear chemistry |
| Zdroj: | Journal of Agricultural and Food Chemistry. 50:1318-1324 |
| ISSN: | 1520-5118 0021-8561 |
| DOI: | 10.1021/jf010955g |
| Popis: | Incubation of fumonisin B(1) and D-glucose in aqueous solutions resulted in the formation of N-(1-deoxy-D-fructos-1-yl) fumonisin B(1) in addition to the previously reported N-(carboxymethyl) fumonisin B(1). N-(1-Deoxy-D-fructos-1-yl) fumonisin B(1) is the first stable product formed after the Amadori rearrangement of the Schiff base formed by the reaction of the primary amine of fumonisin B(1) and the aldehyde group of D-glucose. N-(1-Deoxy-D-fructos-1-yl) fumonisin B(1) was synthesized by reacting fumonisin B(1) with an excess of D-glucose in methanol and heating for 6 h at 64 degrees C. It was purified using C(18) and strong cation exchange solid-phase extraction cartridges and characterized by nuclear magnetic resonance and liquid chromatography-mass spectrometry. Subsequently, N,N-dimethylformamide was found to be a better reaction solvent, requiring reaction for only 2-3 h at 64 degrees C and eliminating the formation of methyl esters. Alkaline hydrolysis of N-(1-deoxy-D-fructos-1-yl) fumonisin B(1) gave a mixture of hydrolyzed fumonisin B(1) and hydrolyzed N-(carboxymethyl) fumonisin B(1). |
| Databáze: | OpenAIRE |
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