engleski

Formose reaction – towards the detection of products

Formose reaction is a very important method for synthesis of monosaccharides and sugar-like substances from a very simple molecule - formaldehyde. First findings date back to 1861 when Buterlow 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 for condensation of formaldehyde. The first process, formation of glycoladehyde from two molecules of formaldehyde, is a very slow process. Once glycolaldehyde is formed, a fast autocatalytic process is initiated to produce more glycolaldehyde and various straight and branched carbohydrates. Formose reaction, due to its autocatalytic nature, possible retro aldol reactions in alkaline medium and side reactions (e.g. Cannizzaro reaction), is still not fully revealed and understood. We would like to contribute to the elucidation of the reaction mechanism and kinetics of formose reaction by mass spectrometry. However, the detection of sugar-like substances is not straightforward. We have tested electrospray ionization (ESI) and atmospheric-pressure chemical ionization (APCI) in both positive and negative mode. We were able to detect sugar- like substances (CH2O)n as deprotonated in negative mode. Better ionization was observed using APCI.

formose reaction ; formaldehyde ; sugars

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