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On the formation of carbonate adducts of fatty alcohols, sterols, and sugars in biological conditions
Author(s) -
do Lago Claudimir L.,
Vidal Denis T. R.,
Rossi Marcelo R.,
Hotta Guilherme M.,
da Costa Eric T.
Publication year - 2012
Publication title -
electrophoresis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.666
H-Index - 158
eISSN - 1522-2683
pISSN - 0173-0835
DOI - 10.1002/elps.201200080
Subject(s) - chemistry , bicarbonate , adduct , hydronium , carbonate , equilibrium constant , aqueous solution , cyclohexanol , fructose , organic chemistry , catalysis , chromatography , inorganic chemistry , molecule
The formation and properties of carbonate adducts of some organic hydroxy compounds in aqueous medium were investigated. Fatty alcohols and sugars were chosen as representative classes of biological interest, and the medium was carbonated aqueous solution with p H ranging from 3.0 to 8.3. Capillary electrophoresis with two capacitively coupled contactless conductivity detectors ( C 4 D s) was used for quantitation and to obtain the mobility of the monoalkyl carbonates ( MAC s), which were used to determine the equilibrium and kinetic constants of the reaction as well as the diffusion coefficients. For increasing chain length of the alcohols, the equilibrium constant tends to the unit, which suggests that fatty alcohols can form the corresponding MAC s. The formation of MAC s for cyclohexanol and cyclopentanol also suggest the existence of similar species for sterols. Carbonate adducts of fructose, glucose, and sucrose were also detected, which suggests that these counterparts of the well‐known phosphates can also occur in the cytosol. Our calculations suggest that one in 1000 to one in 10 000 molecules of these hydroxy compounds would be available as the corresponding MAC in such a medium. Experiments carried out at p H values less than 3.0 showed that there is a catalytic effect of hydronium on the interconversion of bicarbonate and a MAC . Taking into account the great number of hydroxy compounds similar to the ones investigated and that bicarbonate is ubiquitous in living cells, one can anticipate the existence of a whole new class of carbonate adducts of these metabolites.