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Tritium-Labeled Compounds XII. Note on the Synthesis of d-Glucose- and d-Mannose-.
J Res Natl Bur Stand A Phys Chem
January 1969
Institute for Materials Research, National Bureau of Standards, Washington, D.C. 20234.
d-Glucose- and d-mannose- have been synthesized from sodium 2--d-gluconate (sodium d--hexulosonate). Reduction of the salt with lithium borohydride- produced the epimeric, 2-labeled aldonic acids in almost equal proportions. The acids, separated by carrier techniques, were lactonized, and the lactones were reduced with sodium amalgam to the corresponding sugars.
View Article and Find Full Text PDFCrystalline and Forms of 3---d-Glucopyranosyl-d-arabinopyranose.
J Res Natl Bur Stand A Phys Chem
January 1968
Institute for Materials Research, National Bureau of Standards, Washington, D.C. 20234.
Crystalline 3---d-glucopyranosyl--d-arabinopyranose monohydrate, mp 120 to 121 °C, and 3---d-gluecopyranosyl--d-arabinopyranose, mp 155 to 157 °C, were prepared from a sirup obtained by the Ruff degradation of calcium maltobionate. For the monohydrate, , and for the anhydrous form, . The structure of the sugar was established by converting it into maltose.
View Article and Find Full Text PDFDeuterium Isotope Effects in Pyranose and in Pyranose-Furanose Interconversions.
J Res Natl Bur Stand A Phys Chem
January 1967
Institute for Materials Research, National Bureau of Standards, Washington, D.C. 20234.
Rates of mutarotation, catalytic coefficients, and isotope effects are reported for the mutarotations of -d-xylose, -d-glucose, and -d-fructose in HO and in DO at 20 °C. The isotope effects ( ) for the mutarotation of -d-fructose (a pyranose-furanose interconversion) parallel in striking manner the isotope effects for the mutarotation of -d-glucose (an pyranose anomerization). For each sugar, the isotope effect is lowest for the acid-catalyzed reaction, and highest for the water-catalyzed reaction.
View Article and Find Full Text PDFd-Glucose-3- has been prepared by means of three, successive Kiliani syntheses. The process consists of (a) the addition of C-labeled-cyanide to d-glyceraldehyde; (b) hydrolysis of the cyanohydrins and conversion of the resulting epimeric d-tetronic--C acids into d-tetroses-1-C by way of an improved Rosenmund reduction of the acetylated tetronyl chlorides: (c) addition of nonlabeled cyanide to the mixture of the acetates of d-threose-- and d-erythrose-- : (d) hydrolysis of the cyanohydrins, and lactonization of the resulting mixture of four d-pentonic--C acids; (e) chromato-graphic separation of these into three fractions; (f) reduction of the fraction containing d-arabinono- and d-xylono-2-C-lactone to the corresponding sugars, and chromatographic separation of these; and (g) conversion of d-arabinose-2-C into d-glucose-3-C and d-mannose-3- by a third Kiliani synthesis. Approximately 3 percent of the radioactivity was obtained in the form of d-glucose-3-C The process results in the production of a large number of intermediate labeled compounds.
View Article and Find Full Text PDFTritium-Labeled Compounds. XI. Mechanism for the Oxidation of Aldehydes and Aldoses-- With Sodium Chlorite.
J Res Natl Bur Stand A Phys Chem
June 1964
Measurements of kinetic isotope-effects () for the oxidation of ten aldoses- with sodium chlorite in acid solution gave values ranging from 0.56 to 0.75, with an average of 0.
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