title: Carbon exchange in hot alkaline degradation of glucose.
abstract: The decomposition of 1-13C-D-glucose, 6-13C-D-glucose, and 1-13C-sodium lactate has been studied in hot (145 +/- 3 degrees 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 of lactate from glucose the carboxylate (COO-) carbon is formed preferentially from C1 carbons but methyl (CH3) carbon is formed preferentially from C6 carbons. However, on further decomposition of lactate to ethanol and carbonate, 13C-labeled carboxylate (COO-) is scrambled equally among carbonate and both carbons in product ethanol molecules. In the production of glycolate, the labeled C1 carbon mainly ends up as carboxylate (COO-) carbon, while for C6-labeled glucose the labeled carbon mainly ends up as alcoholic (CH2OH) carbon. In the production of acetate and formate there is also discrimination between C1 and C6 label.
authors.affiliation: Department of Chemistry, Materials and Forensic Science, University of Technology Sydney, P.O. Box 123, Broadway, NSW 2007, Australia.
authors.forename: Amanda V
authors.initials: AV
authors.lastname: Ellis
authors.forename: Michael A
authors.initials: MA
authors.lastname: Wilson
mesh_terms: D000085:Acetates / Q000737:chemistry; D000438:Alcohols / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002247:Carbon Isotopes; D002254:Carbonates / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D002384:Catalysis; D005947:Glucose / Q000737:chemistry*; D006016:Glycolates / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D007773:Lactates / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D014867:Water
chemical_list: D000085:Acetates; D000438:Alcohols; D002247:Carbon Isotopes; D002254:Carbonates; D002264:Carboxylic Acids; D006016:Glycolates; D007773:Lactates; D014867:Water; C031149:glycolic acid; D002244:Carbon; D005947:Glucose