/sup 18/O isotope shift in /sup 13/C nuclear magnetic resonance spectroscopy. 12. Position of bond cleavage in the acid-catalyzed hydrolysis of sucrose

Journal Article · Wed Sep 14 04:00:00 EDT 1988 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00227a017· OSTI ID:6187776

Mega, T L; Van Etten, R L

The /sup 18/O isotope-induced shift in /sup 13/C NMR spectroscopy was used to elucidate the point of bond cleavage in the acid-catalyzed hydrolysis of sucrose. Sucrose was hydrolyzed in the presence of H/sub 2//sup 18/O, and the incorporation of /sup 18/O into the several anomeric products was simultaneously assayed as a function of time. While the equilibrium ratio of /sup 18/O was detected in the fructose anomers throughout the course of the hydrolysis, the percentage incorporation of /sup 18/O into the glucose anomers slowly increased to the equilibrium ratio. Independent experimental evidence was obtained with /sup 1/H NMR; the ratio of ..beta..-glucose to ..cap alpha..-glucose was observed to increase from an initially detected value of less than 2:3 to the equilibrium value of greater than 3:2 during the hydrolysis reaction. The data from the NMR experiments were quantitated and compared to theoretical models based on hydrolysis mechanisms involving fructosyl-oxygen bond cleavage and glucosyl-oxygen bond cleavage. The results clearly indicate fructosyl-oxygen bond cleavage under the reaction conditions employed. 39 references, 4 figures.

• Research Organization: Purdue Univ., West Lafayette, IN (USA)
• OSTI ID: 6187776
• Journal Information: J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 110:19; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
400202 -- Isotope Effects
Isotope Exchange
& Isotope Separation
ALDEHYDES
CARBOHYDRATES
CARBON 13
CARBON ISOTOPES
CHEMICAL BONDS
DATA
EVEN-EVEN NUCLEI
EVEN-ODD NUCLEI
EXPERIMENTAL DATA
GLUCOSE
HEXOSES
INFORMATION
ISOTOPES
LIGHT NUCLEI
MONOSACCHARIDES
NMR SPECTRA
NUCLEI
NUMERICAL DATA
ORGANIC COMPOUNDS
OXYGEN 18
OXYGEN ISOTOPES
SACCHARIDES
SPECTRA
SPECTRAL SHIFT
STABLE ISOTOPES