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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/REAXYS Number:
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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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J J Blum
The Journal of protozoology, 39(5), 613-618 (1992-09-01)
Leishmania donovani promastigotes were grown to late log phase, washed and resuspended in iso-osmotic buffer containing L-arginine, and the rate of urea formation was then measured under various conditions. Addition of glucose or mannose activated urea formation, whereas 2-deoxyglucose inhibited
C Parker et al.
Applied and environmental microbiology, 63(2), 543-546 (1997-02-01)
Listeria monocytogenes transported glucose by a high-affinity phosphoenolpyruvate-dependent phosphotransferase system and a low-affinity proton motive force-mediated system. The low-affinity system (Km = 2.9 mM) was inhibited by 2-deoxyglucose and 6-deoxyglucose, whereas the high-affinity system (Km = 0.11 mM) was inhibited
Rare phenazine L-quinovose esters from a marine actinomycete
Pathirana C, et al.
The Journal of Organic Chemistry, 57(2), 740-742 (1992)
Dorthe Villadsen et al.
Plant molecular biology, 55(4), 467-477 (2004-12-18)
The response of some plant genes to glucose analogues 3-O-methylglucose (3OMG) or 6-deoxyglucose (6DOG) has been cited as evidence for metabolism-independent glucose signalling. To analyse such signalling using a genetic approach, we sought to identify Arabidopsis glucose-responsive genes which also
T Roitsch et al.
Plant physiology, 108(1), 285-294 (1995-05-01)
Photoautotrophic suspension-culture cells of Chenopodium rubrum that were shifted to mixotrophic growth by adding glucose were used as model system to investigate the influence of the source-sink transition in higher plants on the expression and enzyme activities of intracellular and
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