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D9761

Sigma-Aldrich

6-Deoxy-D-glucose

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Synonym(s):
D-Isorhamnose, Epifucose, Quinovose
Empirical Formula (Hill Notation):
C6H12O5
CAS Number:
Molecular Weight:
164.16
Beilstein/REAXYS Number:
1723317
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.52

grade

Molecular Biology
for molecular biology

Quality Level

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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1 of 4

This Item
552003G7000G6875
vibrant-m

D9761

6-Deoxy-D-glucose

vibrant-m

552003

D-Glucose-1,2,3,4,5,6,6-d7

grade

Molecular Biology, for molecular biology

grade

-

grade

-

grade

-

assay

≥98% (TLC)

assay

99% (CP)

assay

≥97% (Enzymatic Purity, anhydrous)

assay

≥97% (HPLC)

storage temp.

−20°C

storage temp.

-

storage temp.

−20°C

storage temp.

−20°C

form

powder

form

powder

form

powder

form

powder

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)


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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
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
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
J V Pego et al.
Plant physiology, 119(3), 1017-1023 (1999-03-09)
Low concentrations of the glucose (Glc) analog mannose (Man) inhibit germination of Arabidopsis seeds. Man is phosphorylated by hexokinase (HXK), but the absence of germination was not due to ATP or phosphate depletion. The addition of metabolizable sugars reversed the
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.

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