engleski

The sweet life of the formose reaction

The formose reaction is an important method for synthesis of monosaccharides from a simple molecule - formaldehyde. It is often mentioned in the context of a possible formation of carbohydrates in prebiotic life. First findings date back to 1861 when Butlerow noticed the formation of sugar-like substances after treatment of formaldehyde solution with a base. In 1959 Breslow proposed a mechanism involving two different processes. The first process, formation of glycolaldehyde from two molecules of formaldehyde, is a very slow process. Once glycolaldehyde is formed, a fast-autocatalytic process is initiated to produce unselectively various straight and branched carbohydrates. We would like to contribute to the elucidation of the reaction mechanism and kinetics of the formose reaction by mass spectrometry and ion spectroscopy. We monitor this reaction in time by direct infusion into a mass spectrometer. We initiate the fast-autocatalytic process by the addition of dihydroxyacetone after which the sugars start to grow, and we can detect them in the form of cationic calcium and potassium complexes. We use ion mobility separation mass spectrometry to analyze the formed sugars based on their masses and shapes. The key sugar intermediates are further analyzed by infrared photodissociation spectroscopy.

Formose ; Formaldehyde ; Sugars ; Mass spectrometry

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