The use of Boric Acid for the Determination of the Configuration of Carbohydrates

Publisher Summary This chapter discusses the use of boric acid for the determination of the configuration of carbohydrates. For the polyhydroxy compounds, the conductivity in water and subsequently in 0.5 M boric acid at 25°C is determined. Aliphatic, noncyclic glycols without adjacent hydroxyl groups have no effect, and they cannot form cyclic complexes. With an increase in number of adjacent groups, two hydroxyl groups are more favorably situated with reference to one another, as is unmistakably shown by the following results of determinations. The α-hydroxy acids cause a very considerable increase in the conductivity of boric acid; this may be explained by assuming that the carboxyl group is hydrated to C(OH)*, as a result of which a very favorable situation prevails in these acids for the formation of a boric acid complex.

[1]  K. Sjöberg,et al.  Die Aceton‐Verbindungen der Xylose , 1923 .

[2]  H. Sachse.  Ueber die geometrischen Isomerien der Hexamethylenderivate , 1890 .

[3]  T. Lowry,et al.  XCI.—Studies of dynamic isomerism. Part XXVI. Consecutive changes in the mutarotation of galactose , 1928 .

[4]  C. N. Riiber.  Über Mutarotation (II. Mitteilung) , 1922 .

[5]  H. Isbell,et al.  Pyranose-furanose interconversions with reference to the mutarotations of galactose, levulose, lactulose,and turanose , 1938 .

[6]  E. Mohr.  Die Baeyersche Spannungstheorie und die Struktur des Diamanten , 1918 .

[7]  Paneth.  Das Leitvermögen der Elektrolyte , 1917 .

[8]  N. Vermaas.  Investigations on the equilibria of the boric acid‐diol‐water‐system. I , 2010 .

[9]  C. Hudson,et al.  Studies on the Cleavage of the Carbon Chain of Glycosides by Oxidation. A New Method for Determining Ring Structures and Alpha and Beta Configurations of Glycosides1 , 1937 .

[10]  J. Böeseken.  Über die Lagerung der Hydroxyl‐Gruppen von Polyoxy‐Verbindungen im Raum. Die Konfiguration der gesättigten Glykole und der α‐ und β‐Glykose , 1913 .

[11]  P. Hermans.  Über die Konstitution der Borsäuren und einiger ihrer Derivate , 1925 .

[12]  K. Freudenberg,et al.  Zur Kenntnis der Aceton‐Zucker, II.: Diaceton‐xylose , 1922 .

[13]  K. Freudenberg,et al.  Zur Kenntnis der Aceton-Zucker, IV.: Versuche mit Galaktose und Mannose , 1923 .

[14]  C. N. Riiber,et al.  Eine dritte Modifikation der Galaktose (VII. Mitteilung über Mutarotation) , 1926 .

[15]  W. Haworth,et al.  LXXXI.—The constitution of the disaccharides. Part XII. Lactose , 2022 .

[16]  J. Meulenhoff.  Über das Optisch aktive Boratom , 1925 .

[17]  H. Isbell,et al.  Bromine oxidation and mutarotation measurements of the alpha- and beta-aldoses , 1937 .

[18]  J. Böeseken.  Notiz über den Gleichgewichts- und den Bewegungszustand der Moleküle im Raum , 1923 .