70849-31-9

Basic information

• Product Name: D-MANNOSE-1-13C
• Synonyms: D-MANNOSE-1-13C;D-[1-13C]MANNOSE
• CAS NO: 70849-31-9
• Molecular Formula: C₆H₁₂O₆
• Molecular Weight: 181.16
• Product Categories: 13C & 2H Sugars;Alphabetical Listings;MStable Isotopes;Stable Isotopes;Sugars;Carbohydrates & Derivatives, Isotope Labeled Compounds
• Mol File: 70849-31-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 133 °C(lit.)
• Appearance: /
• Density: 1.732g/cm³
• Refractive Index: 1.635
• CAS DataBase Reference: D-MANNOSE-1-13C(CAS DataBase Reference)
• NIST Chemistry Reference: D-MANNOSE-1-13C(70849-31-9)
• EPA Substance Registry System: D-MANNOSE-1-13C(70849-31-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 70849-31-9(Hazardous Substances Data)

Usage

Uses

(D-Mannose-1-13C) D-Mannose is a carbohydrate that is important in the glycosylation of molecules in a variety of cellular processes. It is involved in N and O glycosylation of bovine why protein products, used in infant formulas. It is also responsible for the O-glycosylation of the T helper cell-derived cytokine interlukin-17A, an important cell-signaling molecule. This is the labeled analog.

InChI:InChI=1/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5+,6?/m1/s1/i6+1

Upstream product

• 10323-20-3 D-Arabinose 
• 70849-16-0 D-<2-13C>glucose 

Downstream Products

• 132202-29-0 <1-13C>Mannitol 
• 40762-22-9 [1-13C]D-glucose 
• 70849-16-0 D-<2-13C>glucose 

Relevant articles and documents

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.