Synthesis of 2-deoxy-(6-/sup 13/C)glucose

Conference · Fri May 01 00:00:00 EDT 1987 · Fed. Proc., Fed. Am. Soc. Exp. Biol.; (United States)

OSTI ID:6081023

Walker, T E; Unkefer, C J; Ehler, D S

The authors have prepared 2-deoxy-D-(6-/sup 13/C)glucose which will be used to test the stability of 2-deoxy-D-glucose-6-phosphate in brain tissue. They chose to label 2-deoxy-D-glucose at C-6 because of the large chemical shift difference between C-6 in the free sugar and C-6 in the 6-phosphate analog. Their synthetic scheme is similar to that used for the synthesis of D-(6-/sup 13/C)glucose which involves the removal of C-6 from D-glucose followed by its replacement with /sup 13/C. They first prepare the methyl ..cap alpha..-furanoside using trifluoroacetic acid in methanol. This product is then treated with periodate which cleaves only between C-5 and C-6 to form a hydrated aldehyde which is reacted directly with K/sup 13/CN to form a mixture of nitriles. The enriched nitriles are reduced with hydrogen to a mixture of 6-aldehydo sugars using a 5% Pd on carbon catalyst. These sugars are reduced with NaBH/sub 4/ to a mixture of labeled methyl furanosides. Acid hydrolysis followed by chromatography yields 2-deoxy-D-(6-/sup 13/C)glucose in an overall yield of 10% from K/sup 13/CN.

• Research Organization: Los Alamos National Lab., NM
• OSTI ID: 6081023
• Report Number(s): CONF-870644-
• Journal Information: Fed. Proc., Fed. Am. Soc. Exp. Biol.; (United States), Journal Name: Fed. Proc., Fed. Am. Soc. Exp. Biol.; (United States) Vol. 46:6; ISSN FEPRA
• Country of Publication: United States
• Language: English

Related Subjects

550200* -- Biochemistry
59 BASIC BIOLOGICAL SCIENCES
ACID HYDROLYSIS
ALDEHYDES
BODY
BRAIN
CARBOHYDRATES
CARBON 13
CARBON ISOTOPES
CENTRAL NERVOUS SYSTEM
CHEMICAL PREPARATION
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHROMATOGRAPHY
DECOMPOSITION
EVEN-ODD NUCLEI
GLUCOSE
HEXOSES
HYDROLYSIS
ISOTOPE APPLICATIONS
ISOTOPES
LIGHT NUCLEI
LYSIS
MONOSACCHARIDES
NERVOUS SYSTEM
NUCLEI
ORGANIC COMPOUNDS
ORGANS
SACCHARIDES
SEPARATION PROCESSES
SOLVOLYSIS
STABLE ISOTOPES
SYNTHESIS
TRACER TECHNIQUES