131771-46-5

Usage

Uses

Used in Biochemical Research:
D-[1-13C]THREO-PENT-2-ULOSE is used as a tracer compound for studying metabolic pathways and enzyme mechanisms in biochemical research. The incorporation of the 13C isotope enables researchers to track the compound's movement and interactions within biological systems, providing valuable insights into various metabolic processes.
Used in Fermentation Industry:
D-[1-13C]THREO-PENT-2-ULOSE is used as a substrate for the production of ethanol through fermentation. As the D-[1-13C]Xylulose labeled analog, it can be utilized in the fermentation process to produce ethanol, which is a widely used biofuel and industrial chemical. The use of this labeled analog can help researchers understand the fermentation process and optimize it for higher yields and efficiency.

Upstream product

• 453-17-8 D-Glyceraldehyde 
• 131000-15-2 (2,3-13C₂)-D,L-Serine 
• 101615-89-8 D-[1,2,3,4,5,6-¹³C₆]glucose 
• 65861-56-5 <1-¹³C>D-Fructose 6-phosphate 
• 1384936-56-4 D-[1,3-⁽¹³⁾C]-glucosone 
• 1384936-55-3 D-[1,2-⁽¹³⁾C]-glucosone 
• 1384936-54-2 D-[2-⁽¹³⁾C]-glucosone 
• 1384936-53-1 D-[1-⁽¹³⁾C]-glucosone 

Relevant academic research and scientific papers

Mass spectrometric studies of the path of carbon in photosynthesis: Positional isotopic analysis of 13C-labelled C4 to C7 sugar phosphates

The (EIMS) electron ionization mass spectrometric fragmentation patterns of the methoxime- and ethoximetrimethylsilyl (TMS) derivatives of C4 to C7 sugars involved as phosphates in the Calvin pathway of photosynthesis in plants were analysed by gas chromatography/EIMS using specifically labelled 13C analogs. In general, most but not all of the major ions in the mass spectra arise from single carbon-carbon bond cleavages of the straight-chain derivatives. The results confirm that GC/MS of the alkoxime-TMS derivatives is a viable method for measuring 163C incorporations at individual carbon atoms in each of the sugar phosphates during photosynthetic experiments with 13CO2. Copyright

Phosphate-catalyzed degradation of d-glucosone in aqueous solution is accompanied by C1-C2 transposition

Pathways in the degradation of the C6 1,2-dicarbonyl sugar (osone) d-glucosone 2 (d-arabino-hexos-2-ulose) in aqueous phosphate buffer at pH 7.5 and 37 °C have been investigated by 13C and 1H NMR spectroscopy with the use of singly and doubly 13C-labeled isotopomers of 2. Unlike its 3-deoxy analogue, 3-deoxy-d-glucosone (3-deoxy-d-erythro-hexos-2-ulose) (1), 2 does not degrade via a 1,2-hydrogen shift mechanism but instead initially undergoes C1-C2 bond cleavage to yield d-ribulose 3 and formate. The latter bond cleavage occurs via a 1,3-dicarbonyl intermediate initially produced by enolization at C3 of 2. However, a careful monitoring of the fates of the sketetal carbons of 2 during its conversion to 3 revealed unexpectedly that C1-C2 bond cleavage is accompanied by C1-C2 transposition in about 1 out of every 10 transformations. Furthermore, the degradation of 2 is catalyzed by inorganic phosphate (Pi), and by the Pi-surrogate, arsenate. C1-C2 transposition was also observed during the degradation of the C5 osone, d-xylosone (d-threo-pentose-2- ulose), showing that this transposition may be a common feature in the breakdown of 1,2-dicarbonyl sugars bearing an hydroxyl group at C3. Mechanisms involving the reversible formation of phosphate adducts to 2 are proposed to explain the mode of Pi catalysis and the C1-C2 transposition. These findings suggest that the breakdown of 2 in vivo is probably catalyzed by Pi and likely involves C1-C2 transposition.

Analysis of metabolic pathways via quantitative prediction of isotope labeling patterns: A retrobiosynthetic 13C NMR study on the monoterpene loganin

The monoterpene loganin serves as a precursor in the biosynthetic pathways of numerous indole alkaloids. In contrast to earlier studies, we present evidence that the biosynthesis of loganin in Rauwolfia serpentina cells proceeds mainly via the deoxyxylulose pathway and not by the mevalonate pathway. This conclusion is based on experiments using a R. serpentina cell culture supplied with 13C-labeled samples of glucose, ribose/ribulose, pyruvate or glycerol. Loganin was isolated from biomass, and the hydrolysis of cellular protein afforded amino acids. The isolated metabolites were analyzed by NMR spectroscopy. The 13C-labeling patterns of isolated amino acids were then used to reconstruct the labeling patterns of phosphoenol pyruvate, pyruvate and acetyl CoA. These labeling patterns were subsequently used to predict labeling patterns for dimethylallyl pyrophosphate and isopentenyl pyrophosphate via the mevalonate and deoxyxylulose pathway, respectively. The observed labeling patterns of the terpenoid moieties in loganin were in excellent agreement with the deoxyxylulose prediction. The minor incorporation of mevalonate into loganin observed in earlier studies can be attributed to metabolite exchange between the two terpenoid pathways. The possibility of crosstalk between the two pathways in plants and plant cell cultures stresses the need for a quantitative analysis of general carbon metabolism in order to determine the partitioning between the mevalonate and deoxyxylulose pathway. The present study shows that a wide variety of general metabolic precursors can fulfill this task in conjunction with the retrobiosynthetic concept.

Enzymes as reagents in organic chemistry: transketolase-catalyzed synthesis of D-xylulose

Oxidation of commercial DL-serine by D-amino acid oxidase gave hydroxypyruvate, the condensation of which with D-glyceraldehyde, catalysed by transketolase (partially purified from spinach leaves), gave D-threo-pentulose (D-xylulose), which was studied by 13C-n.m.r. spectroscopy.