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D9761

Sigma-Aldrich

6-Deoxy-D-glucose

Synonyme(s) :

D-Isorhamnose, Epifucose, Quinovose

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About This Item

Formule empirique (notation de Hill):
C6H12O5
Numéro CAS:
7658-08-4
Poids moléculaire :
164.16
Numéro Beilstein :
1723317
Numéro CE :
231-622-2
Numéro MDL:
MFCD00061627
Code UNSPSC :
12352200
ID de substance PubChem :
24894327
Nomenclature NACRES :
NA.52

Qualité

Molecular Biology
for molecular biology

Niveau de qualité

200

Pureté

≥98% (TLC)

Forme

powder

Température de stockage

−20°C

Chaîne SMILES 

C[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O

InChI

1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3-,4+,5-,6?/m1/s1

Clé InChI

SHZGCJCMOBCMKK-GASJEMHNSA-N

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Description générale

6-Deoxy-D-glucose is a structural homolog of D-glucose (dextrose) and stable analog. It lacks the hydroxyl group at carbon 6 position. It is also an analog of mannose.

Application

6-Deoxy-D-glucose has been used as a standard in the circular dichroism measurements. It has also been used as sugar to incubate starved Dictyostelium HMX44A.atg1-1 cells for microscopy studies.

Actions biochimiques/physiologiques

2-Deoxy-D-glucose (2-DG) is used as a glycolytic inhibitor in studying the biological function of glucose. It is not metabolized, induces endoplasmic reticulum stress and hence, blocks the carbohydrate metabolism in cancer cells. It has therapeutic potential in targeting chemo-resistant hypoxic cancer cells. 2-DG halts the N-linked glycosylation by replacing mannose.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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D Granot et al.
Proceedings of the National Academy of Sciences of the United States of America, 88(13), 5724-5728 (1991-07-01)
Nutrients play a critical role in the decision to initiate a new cell cycle. Addition of nutrients to arrested cells such as stationary-phase cells and spores induces them to begin growth. We have analyzed the nutrients required to induce early
A H Romano
Journal of bacteriology, 152(3), 1295-1297 (1982-12-01)
6-Deoxy-D-glucose, a structural homomorph of D-glucose which lacks a hydroxyl group at carbon 6 and thus cannot be phosphorylated, is transported by Saccharomyces cerevisiae via a facilitated diffusion system with affinity equivalent to that shown with D-glucose. This finding supports
C Laporte et al.
Cell death and differentiation, 14(2), 266-274 (2006-07-01)
While necrotic cell death is attracting considerable interest, its molecular bases are still poorly understood. Investigations in simple biological models, taken for instance outside the animal kingdom, may benefit from less interference from other cell death mechanisms and from better
Cristina De Castro et al.
Glycobiology, 23(3), 346-353 (2012-10-19)
A major virulence factor for Yersinia pseudotuberculosis is lipopolysaccharide, including O-polysaccharide (OPS). Currently, the OPS based serotyping scheme for Y. pseudotuberculosis includes 21 known O-serotypes, with genetic and structural data available for 17 of them. The completion of the OPS
A J Fry et al.
Molecular and biochemical parasitology, 60(1), 9-18 (1993-07-01)
Kinetic parameters for entry of D-fructose into Trypanosoma brucei brucei have been determined. The net uptake of D-fructose was found to be rapid and occurred at a rate which was comparable with that observed for uptake of D-glucose. The Km
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