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2-Keto-D-glucose

≥98.0% (TLC)

Synonym(s):

D-Glucosone

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About This Item

Empirical Formula (Hill Notation):
C6H10O6
CAS Number:
Molecular Weight:
178.14
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25

Assay

≥98.0% (TLC)

form

solid

color

white to beige

storage temp.

2-8°C

SMILES string

OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)C=O

InChI

1S/C6H10O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,4-6,8,10-12H,2H2/t4-,5-,6-/m1/s1

InChI key

DCNMIDLYWOTSGK-HSUXUTPPSA-N

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Application

2-Keto-D-glucose (D-Glucosone) is a key intermediate of a secondary metabolic pathway leading to the antibiotic cortalcerone. D-Glucosone is a substrate that may be used to identify, differentiate and characterize hexokinase(s).

Biochem/physiol Actions

2-Keto-D-glucose is the key intermediate of a secondary metabolic pathway leading to the antibiotic β-pyrone cortalcerone. This antibiotic offers protection to fungi against bacteria. The enzymatic oxidation of d-glucose by pyanose 2 oxidase results in 2-keto-D-glucose, and is considered as rare sugar.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Torbjörn Linden et al.
Kidney international, 62(2), 697-703 (2002-07-12)
Bioincompatible glucose degradation products (GDPs) in fluids for peritoneal dialysis (PD) develop during sterilization and storage. Their biological activity has successfully been monitored through the use of various in vitro methods but their molecular and chemical nature is less well
Teruyuki Usui et al.
Bioscience, biotechnology, and biochemistry, 71(9), 2162-2168 (2007-09-11)
Glyceraldehyde (GLA) was determined in glucose degradation and glycation. GLA was detected as a decahydroacridine-1,8-dione derivative on reversed phase HPLC using cyclohexane-1,3-dione derivatizing reagent. The glucose-derived GLA level was higher than the glycation-derived GLA level, because GLA was converted to
Fungal pyranose oxidases: occurrence, properties and biotechnical applications in carbohydrate chemistry
Giffhorn F
Applied Microbiology and Biotechnology, 54(6), 727-740 (2000)
Wenhui Zhang et al.
Journal of the American Chemical Society, 134(28), 11511-11524 (2012-06-02)
Pathways in the degradation of the C(6) 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 (13)C and (1)H NMR spectroscopy with the use of singly and doubly (13)C-labeled
Kunchala Rungsrisuriyachai et al.
Archives of biochemistry and biophysics, 483(1), 10-15 (2009-01-17)
The flavin-dependent pyranose 2-oxidase catalyzes the oxidation of d-glucose and other pyranoses at the C2 atom to yield 2-keto-sugars and hydrogen peroxide. Here, the steady-state kinetic mechanism of the enzyme from Trametes ochracea was investigated as a function of pH.

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