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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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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
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
Rare phenazine L-quinovose esters from a marine actinomycete
Pathirana C, et al.
The Journal of Organic Chemistry, 57(2), 740-742 (1992)
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
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