Abstract
Isomerization of D-glucose to fructose and mannose in aqueous solutions of Ca(OH)2 with the initial pH 11.4 in a temperature interval of 20–90 °C was studied by 13C NMR spectroscopy in the presence and absence of dissolved oxygen. In the presence of oxygen, the apparent equilibrium isomerization constant is much lower than that in the absence of oxygen. This is related to the oxidation of monosaccharides to formic and aldonic acids, a decrease in the pH of solutions, and cessation of isomerization at pH < 9.
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References
C. A. Lobry de Bruyn and W. A. Alberda van Ekenstein, Recl. Trav. Chim. Pays-Bas, 1895, 14, 195.
C. A. Lobry de Bruyn and W. A. Alberda van Ekenstein, Recl. Trav. Chim. Pays-Bas, 1897, 16, 256.
J. C. Speck, Jr., Adv. Carbohydr. Chem., 1958, 13, 63.
S. J. Angyal, in Glycoscience: Epimerization, Isomerization, and Rearrangement Reactions of Carbohydrates, Ed. A. F. Stutz, Springer-Verlag, Berlin—Heidelberg, 2001, p. 1.
J. C. Sowden and R. Schaffer, J. Am. Chem. Soc., 1952, 74, 505.
M. L. Wolform and W. L. Lewis, J. Am. Chem. Soc., 1928, 50, 837.
A. M. Kuzin, Zh. Obshch. Khim., 1935, 5, 1373.
R. Yanagihara, K. Saeda, S. Osana, and S. Yshikawa, Bull. Chem. Soc. Jpn, 1997, 66, 2268.
K. Fujino, J. Kobayashi, and I. Higuchi, Nippon Kagaku Kaishi, 1972, 2287.
J. A. Rendelman, Jr., Adv. Carbohydr. Chem., 1966, 21, 209.
H. S. El Khadem, S. Ennifar, and H. S. Isbell, Carbohydr. Res., 1987, 169, 13.
H. S. El Khadem, S. Ennifar, and H. S. Isbell, Carbohydr. Res., 1989, 185, 51.
H. E. Gottlieb, V. Kotlyar, and A. Nudelman, J. Org. Chem., 1997, 62, 7512.
The Sadtler Standard Spectra: C-13 Nuclear Magnetic Resonance Spectra, Sadtler Research Lab., Philadelphia, 1978, No. 822c; No. 4681c.
K. Bock and R. Thoegersen, Ann. Repts NMR Spectroscopy, 1982, 13, 1.
W. B. Gleason and R. Barker, Can. J. Chem., 1971, 49, 1425; 1433.
G. de Wit, A. P. G. Kieboom, and H. van Bekkum, Carbohydr. Res., 1979, 74, 157.
T. I. Khomenko and O. V. Krylov, Kinet. Katal., 1974, 15, 625 [Kinet. Catal., 1974, 15 (Engl. Transl.)].
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1909–1913, August, 2005.
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Simonov, A.N., Pestunova, O.P., Matvienko, L.G. et al. 13C NMR studies of isomerization of D-glucose in an aqueous solution of Ca(OH)2. The effect of molecular oxygen. Russ Chem Bull 54, 1967–1972 (2005). https://doi.org/10.1007/s11172-006-0065-x
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DOI: https://doi.org/10.1007/s11172-006-0065-x