478519-02-7

Basic information

• Product Name: L-[1-13C]GLUCOSE
• Synonyms: L-[1-13C]GLUCOSE
• CAS NO: 478519-02-7
• Molecular Formula: C6H12O6
• Molecular Weight: 181.16
• Product Categories: Carbohydrates & Derivatives, Isotope Labelled Compounds
• Mol File: 478519-02-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: L-[1-13C]GLUCOSE(CAS DataBase Reference)
• NIST Chemistry Reference: L-[1-13C]GLUCOSE(478519-02-7)
• EPA Substance Registry System: L-[1-13C]GLUCOSE(478519-02-7)

Safety Data

• Hazardous Substances Data: 478519-02-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
L-[1-13C]GLUCOSE is used as a key component in the synthesis of L-Glucose Pentaacetate, a potential therapeutic agent for the treatment of type II diabetes. L-[1-13C]GLUCOSE may help regulate blood sugar levels and improve insulin sensitivity, offering a promising avenue for diabetes management.
Used in Medical Diagnostics:
L-[1-13C]GLUCOSE is used as a colon cleansing agent in preparation for a colonoscopy procedure. Its synthetic nature and stable isotope labeling make it suitable for this application, ensuring a thorough cleansing of the colon while minimizing potential side effects.
Used in Research Applications:
L-[1-13C]GLUCOSE, due to its stable isotope labeling, is utilized in research settings to study various biological processes and pathways. The incorporation of carbon-13 allows for the tracking and analysis of glucose metabolism, providing valuable insights into cellular functions and potential therapeutic targets.

Upstream product

• 10323-20-3 D-Arabinose 
• 70849-31-9 <1-13C>-D-mannose 
• 1114-34-7 D-lyxose 
• 58-86-6 D-xylose 
• 50-69-1 D-ribose 
• 213825-55-9 D-(1,5-13C₂)arabinose 
• 139657-61-7 D-(2,5-13C₂)ribose 
• 40010-55-7 <1-13C>-α-D-talopyranose 
• 40010-55-7 β-D-[1-13C]talopyranose 
• 70849-16-0 D-<2-13C>glucose 
• 40010-55-7 α- and β-D-<1-13C>mannose 

Downstream Products

• 1633-56-3 (¹³C)-formic acid 
• 287111-36-8 [U-(13)C6]-mevalonolactone 
• 478506-38-6 C₅⁽¹³⁾CH₁₂O₆ 
• 108311-21-3 <1-13C>-D-fructose 
• 444313-77-3 C₁-¹³C-tri-O-benzyl-D-glucal 

Relevant articles and documents

STABILIZED ACYCLIC SACCHARIDE COMPOSITE AND METHOD FOR STABILIZING ACYCLIC SACCHARIDES AND APPLICATIONS THEREOF

Disclosed is a stabilized acyclic saccharide composite, which includes a LDH-based (layered double hydroxide-based) material and acyclic saccharides intercalated in interlayer regions of the LDH-based material. The acyclic saccharides stabilized and trapped in the LDH-based material give an opportunity for direct functionalization to other valuable molecules in the pharmaceutical, chemical or carbohydrate industries. Further, a novel pathway for saccharide transformation and aldol condensation without the drawbacks associated with enzymatic catalysts is achieved through the acyclic saccharides trapped by the LDH-based material.

Successive C1-C2 bond cleavage: The mechanism of vanadium(v)-catalyzed aerobic oxidation of d-glucose to formic acid in aqueous solution

Vanadium(v)-catalyzed aerobic oxidation in aqueous solution shows high selectivity in the field of C-C bond cleavage of carbohydrates for chemicals with less carbon atoms. However, the pathway of C-C bond cleavage from carbohydrates and the conversion mechanism are unclear. In this work, we studied the pathway and the mechanism of d-glucose oxidation to formic acid (FA) in NaVO3-H2SO4 aqueous solution using isotope-labeled glucoses as substrates. d-Glucose is first transformed to FA and d-arabinose via C1-C2 bond cleavage. d-Arabinose undergoes similar C1-C2 bond cleavage to form FA and the corresponding d-erythrose, which can be further degraded by C1-C2 bond cleavage. Dimerization and aldol condensation between carbohydrates can also proceed to make the reaction a much more complicated mixture. However, the fundamental reaction, C1-C2 bond cleavage, can drive all the intermediates to form the common product FA. Based on the detected intermediates, isotope-labelling experiments, the kinetic isotope effect study and kinetic analysis, this mechanism is proposed. d-Glucose first reacts with a vanadium(v) species to form a five-membered-ring complex. Then, electron transfer occurs and the C1-C2 bond weakens, followed by C1-C2 bond cleavage (with no C-H bond cleavage), to generate the H3COO-vanadium(iv) complex and d-arabinose. FA is generated from H3COO that is oxidized by another vanadium(v) species. The reduced vanadium species is oxidized by O2 to regenerate to its oxidation state. This finding will provide a deeper insight into the process of C-C bond cleavage of carbohydrates for chemical synthesis and provide guidance for screening and synthesizing new highly-efficient catalyst systems for FA production.

Two-bond 13C-13C spin-coupling constants in carbohydrates: New measurements of coupling signs

D-(1,3,6-13C3)Allose (1), (13C)methyl α-D-(1,2-13C2)glucopyranoside (2) and (13C)methyl β-D-(1,2-13C2)glucopyranoside (3) were synthesized and used to establish the signs of their constituent 2J(CCC) or 2J(COC) values (2J(C1,C3) in the α-pyranose of 1 (15), and 2J(C1,CH3) in 2 and 3). Compounds 2, 3 and 15 contain three mutually coupled labeled carbons, thus creating a three-spin system from which crosspeak displacements in 13C-13C COSY-45 spectra were used to determine coupling signs. In all compounds, at least one 3J(CC) value was present as an internal reference: 3J(C2,CH3 in 2 and 3, and 3J(C1,C6) and 3J(C3,C6) in 15. 2J(C1,CH3), in 2 and 3, and 2J(C1,C3) in 15, were found to be negative, thus providing experimental confirmation of the sign predictions made via the projection resultant rule described recently.

D-Talose Anomerization: NMR Methods To Evaluate the Reaction Kinetics

The kinetics of anomerization of the aldohexose, D-talose, have been studied by several NMR methods in order to evaluate their limitations, complementarity, and internal consistency and to futher explore the effect of monosaccharide structure on reactivity.By use of Dtalose and 13C NMR spectroscopy, six tautomeric forms were detected and quantitated in aqueous solution: α- and β-talofuranoses, α- and β-talopyranoses, hydrate (1,1-gem-diol), and aldehyde.The 13C (75-MHz) and 1H (620-MHz) NMR spectra of D-talose have been interpreted, yielding chemical shiftsand coupling constants (JHH, JCC, JCH) that have been evaluated in terms of ring configuration and conformation.By use of 13C saturation-transfer NMR (ST-NMR), ring-opening rate constants (kopen) of the four cyclic forms were measured, and ring-closing rate constants (kclose) were calculated from kopen and equilibrium constants.NMR-derived rates of tautomer equilibration obtained after dissolving α-D-talopyranose in aqueous solution were predicted accurately from a computer treatment of the unidirectional rate constants determined by ST-NMR under similar solution conditions.Two-dimensional 13C exchange spectroscopy was applied to obtain overall rate constants of tautomer interconversion; rate constants obtained in this fashion compared favorably with those calculated from the ST-derived unidirectional rate constants using the steady-state approximation.Kinetic results show that anomeric configuration and ring size significantly affect ring-opening and ring-closing rates of monosaccharides.

HYDROXIDE-CATALYZED ISOMERIZATION OF D-(1-13C)MANNOSE: EVIDENCE FOR THE INVOLVEMENT OF 3,4-ENEDIOLS

The KOH-catalyzed isomerization of D-(1-13C)mannose under anaerobic conditions was studied by 13C-n.m.r. spectroscopy.D-(1-13C)Glucose and D-(1-13C)fructose are generated during the reaction, as expected.In addition, however, (6-13C)glucose, (6-13C)mannose, and (6-13C)fructose are produced in small proportions, possibly via symmetrical 3,4-enediol intermediates.The involvement of the latter structures in 13C-label shifting is inferred from the observation of (1-13C)sorbose and (6-13C)sorbose in the reaction mixture.

Paramolybdate anion-exchange resin, an improved catalyst for the C-1-C-2 rearrangement and 2-epimerization of aldoses.

Aqueous solutions of molybdate at 90 degrees bring about the inversion of the C-1-C-2 fragment of aldoses having four or more carbon atoms, generating thermodynamically equilibrated mixtures of the starting aldose and its 2-epimer. In some cases, notably with the aldopentoses, substantial proportions of the 3-epimers are produced, as well as 2-epimers that have not undergone inversion of the C-1-C-2 fragment. These side-reactions can be controlled by using the paramolybdate form of an anion-exchange resin (AG MP-1) together with the formate form of the same resin. The latter acts to scavenge unbound molybdate and paramolybdate anions that appear to be responsible for the side reactions.