Radiocarbon labeled fully deuterated glucose: Preparation, chromatography and preliminary distribution studies

Conference · Wed May 01 04:00:00 EDT 1985 · J. Nucl. Med.; (United States)

OSTI ID:7033477

Gatley, S J; Wess, M M; Govoni, P L; Wagner, A; Katz, J J; Friedman, A M

Since carbon-deuterium bonds are harder to break than carbon-hydrogen bonds, substitution of deuterium into organic molecules often leads to alterations in metabolism; e.g. fully deuterated glucose (d/sup 7/-G or deuterioglucose) is a poorer substrate than (protio) glucose for the bacterial enzyme, glucose oxidase. Radiolabeled d/sup 7/-G was therefore prepared to search for a possible isotope effect in its biodistribution in mammals. Green algae grown in deuterium oxide for many generations were exposed to C-14 CO/sub 2/ in the light, and then boiled in 2N-HCl. After rotary evaporation of the HCl the residue was passed through H/sup +/-form and CO/sub 3//sup =/-form Dowex columns in water and then passed through silica gel and activated charcoal in ethanol. The major component of the final neutral fraction, d/sup 7/-G was further purified by HPLC on a Bio-Rad HPX-87P column eluted with water. The behavior of d/sup 7/-G on HPX-87P, on an NH-column (Alltech) and on 2D cellulose TLC, was identical with that of glucose. However, on silica gel TLC d/sup 7/-G ran more slowly (R/sub Glc./ = 0.93); this result was confirmed with authentic d/sup 7/-G. In later work, pure C-11 and C-14 d/sup 7/-G were rapidly and conveniently obtained by HPX-87P chromatography of an invertase-treated extract obtained by boiling algae in 80% EtOH. Preliminary tissue distributions and metabolite analyses suggest slow transport of d/sup 7/-G than G into the brain. Exploitation of deuterium isotope effects could become a useful aspect of radiopharmaceutical design.

• Research Organization: Chemistry Dept., Argonne National Lab., IL
• OSTI ID: 7033477
• Report Number(s): CONF-850611-
• Conference Information: Journal Name: J. Nucl. Med.; (United States) Journal Volume: 26:5
• Country of Publication: United States
• Language: English

Related Subjects

38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
400700 -- Radiochemistry & Nuclear Chemistry
550501* -- Metabolism-- Tracer Techniques
59 BASIC BIOLOGICAL SCIENCES
ACTIVATED CARBON
ADSORBENTS
ALCOHOLS
ALDEHYDES
ALGAE
ANIMALS
BETA DECAY RADIOISOTOPES
BETA-PLUS DECAY RADIOISOTOPES
BODY
BRAIN
CARBOHYDRATES
CARBON
CARBON 11
CARBON 14 COMPOUNDS
CARBON COMPOUNDS
CARBON DIOXIDE
CARBON DIOXIDE FIXATION
CARBON ISOTOPES
CARBON OXIDES
CELLULOSE
CENTRAL NERVOUS SYSTEM
CHALCOGENIDES
CHEMICAL PREPARATION
CHROMATOGRAPHY
DEUTERIUM COMPOUNDS
DISTRIBUTION
ELEMENTS
ENZYMES
ETHANOL
EVAPORATION
EVEN-ODD NUCLEI
GLUCOSE
GROWTH
HEAVY WATER
HEXOSES
HYDROCHLORIC ACID
HYDROGEN COMPOUNDS
HYDROXY COMPOUNDS
INORGANIC ACIDS
ION EXCHANGE CHROMATOGRAPHY
ISOTOPE EFFECTS
ISOTOPES
LABELLED COMPOUNDS
LABELLING
LIGHT NUCLEI
LIQUID COLUMN CHROMATOGRAPHY
MAMMALS
METABOLISM
METABOLITES
MINUTES LIVING RADIOISOTOPES
MONOSACCHARIDES
NERVOUS SYSTEM
NONMETALS
NUCLEI
ORGANIC COMPOUNDS
ORGANS
OXIDES
OXIDOREDUCTASES
OXYGEN COMPOUNDS
PHASE TRANSFORMATIONS
PLANTS
POLYSACCHARIDES
RADIOISOTOPES
SACCHARIDES
SEPARATION PROCESSES
SUBSTRATES
SYNTHESIS
THIN-LAYER CHROMATOGRAPHY
TISSUE DISTRIBUTION
VERTEBRATES
WATER