2-Keto-D-Glucose

Names

[ Name ]:
2-Keto-D-Glucose

[Synonym ]:
Arabino-hexosulose
D-arabino-hexosulose
Fructosone
arabino-Hexos-2-ulose
Mannosone
3-deoxyglucosone
(3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexanal
D-Arabino-hexos-2-ulose
2-Keto-D-glucose
2-Ketoglucose
Glucosone

Biological Activity

[Description]:

2-Keto-D-Glucose (D-Glucosone) is a key intermediate in a secondary metabolic pathway leading to the antibiotic Cortalcerone. 2-Keto-D-Glucose is also an intermediate in the conversion of D-glucose into D-fructose. 2-Keto-D-Glucose is found in various natural sources, including fungi, algae, and shellfish[1][2].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Others >> Others

[In Vitro]

Pyrroloquinoline quinone-dependent 2-keto-D-glucose (2KG) dehydrogenase (2KGDH) has high specificity for the oxidation of 2-Keto-D-Glucose to 2-keto-D-gluconic acid (2KGA). P. aureofaciens (Pa2KGDH) specifically preferred 2KG as a substrate and oxidized the C-1 position of 2KG, indicating that the enzyme is a 2KGDH[3].

[References]

[1]. Sun, Lianhong, et al. Engineering galactose oxidase to increase expression level in E. coli, enhance thermostability, and introduce novel activities. Dissertation (Ph.D.), California Institute of Technology.

[2]. zawa K, et al. A novel pyrroloquinoline quinone-dependent 2-keto-D-glucose dehydrogenase from Pseudomonas aureofaciens. J Bacteriol. 2015 Apr;197(8):1322-9.

[3]. Te-ning E.Liu, et al. Convenient, laboratory procedure for producing solid d-arabino-hexos-2-ulose (d-glucosone). Carbohydrate Research. Volume 113, Issue 1, 16 February 1983, Pages 151-157.

Chemical & Physical Properties

[ Density]:
1.574 g/cm3

[ Boiling Point ]:
481ºC at 760 mmHg

[ Melting Point ]:
118-120°C

[ Molecular Formula ]:
C₆H₁₀O₆

[ Molecular Weight ]:
178.14000

[ Flash Point ]:
258.8ºC

[ Exact Mass ]:
178.04800

[ PSA ]:
115.06000

[ Vapour Pressure ]:
2.85E-11mmHg at 25°C

[ Index of Refraction ]:
1.55

[ Storage condition ]:
Hygroscopic, Store under Inert atmosphere -20°C Freezer

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
24/25

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
29144000

Articles

Peroxynitrite induces formation of N( epsilon )-(carboxymethyl) lysine by the cleavage of Amadori product and generation of glucosone and glyoxal from glucose: novel pathways for protein modification by peroxynitrite.

Diabetes 51(9) , 2833-9, (2002)

Accumulation of advanced glycation end products (AGEs) on tissue proteins increases with pathogenesis of diabetic complications and atherosclerosis. Here we examined the effect of peroxynitrite (ONOO(...

Bioconversion of D-glucose into D-glucosone by glucose 2-oxidase from Coriolus versicolor at moderate pressures.

Appl. Biochem. Biotechnol. 163 , 906-917, (2011)

Glucose 2-oxidase (pyranose oxidase, pyranose:oxygen-2-oxidoreductase, EC 1.1.3.10) from Coriolus versicolor catalyses the oxidation of D-glucose at carbon 2 in the presence of molecular O₂ producing ...

Fungal pyranose oxidases: occurrence, properties and biotechnical applications in carbohydrate chemistry.

Appl. Microbiol. Biotechnol. 54 , 727, (2000)

Pyranose oxidases are widespread among lignin-degrading white rot fungi and are localized in the hyphal periplasmic space. They are relatively large flavoproteins which oxidize a number of common mono...