Oxygen Exchange and Bond Cleavage Reactions of Carbohydrates Studied Using the 180 Isotope Shift in 13C NMR Spectroscopy

  • Tony L. Mega
  • Robert L. Van Etten
Part of the Basic Life Sciences book series (BLSC, volume 56)


Isotopic labeling, particularly through the use of 18O-enriched water, has been important in defining our present understanding of the mutarotation process and reactions involving carbohydrate bond cleavage (Rittenberg and Graff, 1958; BeMiller, 1967; Capon, 1969). A related reaction, the exchange of oxygen at the anomeric carbon atom of reducing sugars, may also be observed by the use of 180-water, and an understanding of the kinetics of this exchange process is an important prerequisite to carbohydrate studies such as bond cleavage reactions that make use of the 180 label. Unfortunately, there are relatively few data in the literature that characterize the oxygen exchange reactions of even the most biologically important monosaccharides. No comparable investigation has appeared since Rittenberg and Graff’s study of glucose oxygen exchange in 1958. As a result, meaningful comparisons of oxygen exchange rates between different sugars have been quite difficult due to the wide variety of experimental conditions that have been used (Risley and Van Etten, 1982).


Bond Cleavage Carbonyl Carbon Isotope Shift Oxygen Exchange Bond Cleavage Reaction 
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Copyright information

© Plenum Press, New York 1990

Authors and Affiliations

  • Tony L. Mega
  • Robert L. Van Etten
    • 1
  1. 1.Chemistry DepartmentPurdue UniversityW. LafayetteUSA

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