D9761
6-Deoxy-D-glucose
Synonym(s):
D-Isorhamnose, Epifucose, Quinovose
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About This Item
Empirical Formula (Hill Notation):
C6H12O5
CAS Number:
Molecular Weight:
164.16
UNSPSC Code:
12352200
NACRES:
NA.52
PubChem Substance ID:
EC Number:
231-622-2
Beilstein/REAXYS Number:
1723317
MDL number:
InChI key
SHZGCJCMOBCMKK-GASJEMHNSA-N
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
SMILES string
C[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O
Quality Level
assay
≥98% (TLC)
storage temp.
−20°C
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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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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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 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
Mark W Ruszczycky et al.
Journal of the American Chemical Society, 133(19), 7292-7295 (2011-04-26)
DesII, a radical S-adenosyl-l-methionine (SAM) enzyme from Streptomyces venezuelae, catalyzes the deamination of TDP-4-amino-4,6-dideoxy-D-glucose to TDP-3-keto-4,6-dideoxy-D-glucose in the desosamine biosynthetic pathway. DesII can also catalyze the dehydrogenation of TDP-D-quinovose to the corresponding 3-keto sugar. Similar to other radical SAM enzymes
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
Markus Ralser et al.
Proceedings of the National Academy of Sciences of the United States of America, 105(46), 17807-17811 (2008-11-14)
The glucose analogue 2-deoxy-D-glucose (2-DG) restrains growth of normal and malignant cells, prolongs the lifespan of C. elegans, and is widely used as a glycolytic inhibitor to study metabolic activity with regard to cancer, neurodegeneration, calorie restriction, and aging. Here
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