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D9761

Sigma-Aldrich

6-Deoxy-D-glucose

Synonym(s):

D-Isorhamnose, Epifucose, Quinovose

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About This Item

Empirical Formula (Hill Notation):
C6H12O5
CAS Number:
7658-08-4
Molecular Weight:
164.16
Beilstein:
1723317
EC Number:
231-622-2
MDL number:
MFCD00061627
UNSPSC Code:
12352200
PubChem Substance ID:
24894327
NACRES:
NA.52

grade

Molecular Biology
for molecular biology

Quality Level

200

Assay

≥98% (TLC)

form

powder

storage temp.

−20°C

SMILES string

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

InChI key

SHZGCJCMOBCMKK-GASJEMHNSA-N

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General description

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.

Biochem/physiol Actions

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.

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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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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