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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)

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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
Yi-Rui Wang et al.
Journal of Asian natural products research, 20(11), 1019-1027 (2018-04-05)
Three new dammarane triterpenoid saponins, cyclocariosides O-Q (1-3), were isolated from the ethanolic extracts of the leaves of Cyclocarya paliurus. The structures of these compounds were elucidated by spectroscopic methods.
Haibin Xi et al.
IUBMB life, 66(2), 110-121 (2014-03-01)
Through the eons of time, out of all possible configurations, nature has selected glucose not only as a vital source of energy to sustain life but also as the molecule who's structure supplies the appropriate elements required for a cell
D Massillon et al.
The Journal of biological chemistry, 270(33), 19351-19356 (1995-08-18)
In search for a nonmetabolized, superior glucose analogue to study the mechanism of glucose-induced glycogen synthesis, we have tested 2-deoxy-2-fluoro-alpha-D-glucopyranosyl fluoride, which inhibits muscle phosphorylase beta 10-fold better than dose glucose (Street, I.P., Armstrong, C.R., and Withers, S.G. (1986) Biochemistry
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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