Carbon exchange in hot alkaline degradation of glucose

Publisher:
American Chemical Society
Publication Type:
Journal article
Citation:
Ellis, A. and Wilson, M. 2002 'Carbon exchange in hot alkaline degradation of glucose', Journal of Organic Chemistry, vol. 67, no. 24, pp. 8469-8474.
Issue Date:
2002
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The decomposition ofl-13C-o-glucose, 6-13C-o-glucose, and 1-13C-sodium lactate has been studied in hot (145 ± 3°C) alkaline (3.5 M) sodium hydroxide solution in order to understand the mechanisms of carbon exchange in the alkaline degradation of glucose. The results show that in the formation oflactate from glucose the carboxylate (COO-) carbon is formed preferentially from Cl carbons but methyl (ClIa) carbon is formed preferentially from C6 carbons. However, on further decomposition of lactate to ethanol and carbonate, 13C-Iabeled carboxylate (COO-) is scrambled equally among carbonate and both carbons in product ethanol molecules. In the production of glycolate, the labeled Cl carbon mainly ends up as carboxylate (COO-) carbon, while for C6-labeled glucose the labeled carbon mainly ends up as alcoholic (CH20H) carbon. In the production of acetate and formate there is also discrimination between Cl and C6 label.
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