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.[1] It lacks the hydroxyl group at carbon 6 position. It is also an analog of mannose.[2]

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]

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)