NMR of all-carbon-13 sugars: an application in development of an analytical method for a novel natural sugar, 1,5-anhydrofructose.
Of the all-carbon-13 compounds, glucose is one of the most easily accessible, and therefore we applied 13C-NMR technique to the metabolic study of glucose-related compounds, 1,5-anhydro-D-glucitol and 1,5-anhydro-D-fructose (AF). Applying an INADEQUATE method to the substitutes of these novel sugars fully labeled with carbon-13, we could trace out the entire carbon skeleton with high sensitivity and confirm the chemical structures of these sugars. The method also provided a much easier way to optimize the enzymatic oxidation for AF preparation: we selectively and continuously monitored the quantities, as well as their structures in aqueous solution, of the substrate and products in a noninvasive manner. Similarly relying upon information from the 13C-NMR, we developed a valuable derivatization method of AF for its GC-MS application, which was so sensitive that we were able to demonstrate the natural occurrence of AF in rat liver.
Kametani
S
S
Department of Life Science, Graduate School of Arts and Sciences, The University of Tokyo, Komaba, Meguro-ku.
Mizuno
H
H
Shiga
Y
Y
Akanuma
H
H
D000818:Animals; D002247:Carbon Isotopes; D003847:Deoxyglucose / Q000032:analysis* / Q000737:chemistry / Q000378:metabolism; D005632:Fructose / Q000031:analogs & derivatives* / Q000032:analysis / Q000737:chemistry / Q000378:metabolism; D008099:Liver / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D051381:Rats
D002247:Carbon Isotopes; D005632:Fructose; C006584:1,5-anhydroglucitol; C048927:1,5-anhydrofructose; D003847:Deoxyglucose