| Full text | |
| Author(s): |
dos Santos, Vagner B.
[1]
;
Vidal, Denis T. R.
[1]
;
Francisco, Kelliton J. M.
[1]
;
Ducati, Lucas C.
[1]
;
do Lago, Claudimir L.
[1]
Total Authors: 5
|
| Affiliation: | [1] Univ Sao Paulo, Inst Chem, Dept Fundamental Chem, Av Prof Lineu Prestes 748, BR-05508000 Sao Paulo, SP - Brazil
Total Affiliations: 1
|
| Document type: | Journal article |
| Source: | Carbohydrate Research; v. 428, p. 18-22, JUN 16 2016. |
| Web of Science Citations: | 3 |
| Abstract | |
Hemiesters of carbonic acid can be freely formed in aqueous media containing HCO3-/CO2 and mono- or poly-hydroxy compounds. Herein, C-13 NMR spectroscopy was used to identify isomers formed in aqueous solutions of glycerol (a prototype compound) and seven carbohydrates, as well as to estimate the equilibrium constant of formation (K-eq). Although both isomers are formed, glycerol 1-carbonate corresponds to 90% of the product. While fructose and ribose form an indistinct mixture of isomers, the anomers of D-glucopyranose 6-carbonate correspond to 74% of the eight isomers of glucose carbonate that were detected. The values of K-eq for the disaccharides sucrose (4.3) and maltose (4.2) are about twice the values for the monosaccharides glucose (2.0) and fructose (2.3). Ribose (K-eq = 0.89)-the only sugar without a significant concentration of a species containing a -CH2OH group in an aqueous solution-resulted in the smallest K-eq. On the basis of the K-eq value and the concentrations of HCO3- and glucose in blood, one can anticipate a concentration of 2-4 mu mol L-1 for glucose 6-carbonate, which corresponds to ca. of 10% of its phosphate counterpart (glucose 6-phosphate). (C) 2016 Elsevier Ltd. All rights reserved. (AU) | |
| FAPESP's process: | 11/02156-2 - The use of capillary electrophoresis with contactless conductivity detection for obtaining analytical and physicochemical parameters of peroxycarbonate, peroxyacids, and monoethyl pyrocarbonate. |
| Grantee: | Denis Tadeu Rajh Vidal |
| Support Opportunities: | Scholarships in Brazil - Post-Doctoral |
| FAPESP's process: | 13/14993-1 - Characterization and quantification of monoalkyl carbonates in aqueous medium employing microfluidic devices coupled to a mass spectrometer |
| Grantee: | Vagner Bezerra dos Santos |
| Support Opportunities: | Scholarships in Brazil - Post-Doctoral |
| FAPESP's process: | 12/06642-1 - Formation and properties of adducts of organic hydroxy-compounds with carbonate in aqueous medium and biological conditions |
| Grantee: | Claudimir Lucio Do Lago |
| Support Opportunities: | Regular Research Grants |