Key Documents

View All Documentation

D9761

6-Deoxy-D-glucose

Name: 6-Deoxy-<SC>D</SC>-glucose
Brand: SIGMA

Synonym(s):

D-Isorhamnose, Epifucose, Quinovose

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):

C₆H₁₂O₅

CAS Number:

7658-08-4

Molecular Weight:

164.16

UNSPSC Code:

12352200

NACRES:

NA.52

PubChem Substance ID:

24894327

EC Number:

231-622-2

Beilstein/REAXYS Number:

1723317

MDL number:

MFCD00061627

Technical Service

Need help? Our team of experienced scientists is here for you.

Let Us Assist

Properties

Quality Level

200

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

Description

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)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

0000524236

0000492556

0000478300

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

The O-specific polysaccharide structure and gene cluster of serotype O:12 of the Yersinia pseudotuberculosis complex, and the identification of a novel L-quinovose biosynthesis gene.

Cristina De Castro et al.

Glycobiology, 23(3), 346-353 (2012-10-19)

A major virulence factor for Yersinia pseudotuberculosis is lipopolysaccharide, including O-polysaccharide (OPS). Currently, the OPS based serotyping scheme for Y. pseudotuberculosis includes 21 known O-serotypes, with genetic and structural data available for 17 of them. The completion of the OPS

Glucose induces cAMP-independent growth-related changes in stationary-phase cells of Saccharomyces cerevisiae.

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

Mechanistic studies of the radical S-adenosyl-L-methionine enzyme DesII: EPR characterization of a radical intermediate generated during its catalyzed dehydrogenation of TDP-D-quinovose.

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

View All Related Papers

Global Trade Item Number

SKU	GTIN
D9761-100MG	04061833591093
D9761-250MG	04061833076330