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:
Pricing and availability is not currently available.
Quality Level
grade
Molecular Biology
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
General description
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.[3]
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[1] and hence, blocks the carbohydrate metabolism in cancer cells.[2] It has therapeutic potential in targeting chemo-resistant hypoxic cancer cells. 2-DG halts the N-linked glycosylation by replacing mannose.[2]
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This Item | |||
|---|---|---|---|
| assay ≥98% (TLC) | assay ≥97% (HPLC) | assay 99% (CP) | assay ≥97% (Enzymatic Purity, anhydrous) |
| grade Molecular Biology | grade - | grade - | grade - |
| Quality Level 200 | Quality Level 100 | Quality Level 200 | Quality Level 200 |
| form powder | form powder | form powder | form powder |
| storage temp. −20°C | storage temp. −20°C | storage temp. room temp | storage temp. −20°C |
![2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose ≥97% (HPLC)](/deepweb/assets/sigmaaldrich/product/structures/104/527/40bd5a41-ebc4-484e-a10e-891fecfaea79/640/40bd5a41-ebc4-484e-a10e-891fecfaea79.png)
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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
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
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| D9761-100MG | 04061833591093 |
| D9761-250MG | 04061833076330 |