D9761

6-Deoxy-D-glucose

• Synonym(s): D-Isorhamnose, Epifucose, Quinovose
• 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

Properties

• Quality Segment: 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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)