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.
Department of Life Science, Graduate School of Arts and Sciences, The University of Tokyo, Komaba, Meguro-ku.
S
S
Kametani
H
H
Mizuno
Y
Y
Shiga
H
H
Akanuma
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