D4601

Sigma-Aldrich

2-Deoxy-D-glucose

99%

Synonym(s):
2-Deoxy-D-arabinohexose
Empirical Formula (Hill Notation):
C6H12O5
CAS Number:
Molecular Weight:
164.16
Beilstein/REAXYS Number:
1723331
EC Number:
MDL number:

assay

99%

optical activity

[α]21/D +46.5°, c = 1 in H2O

mp

146-147 °C (lit.)

SMILES string

OC[C@@H](O)[C@@H](O)[C@H](O)CC=O

InChI

1S/C6H12O5/c7-2-1-4(9)6(11)5(10)3-8/h2,4-6,8-11H,1,3H2/t4-,5-,6+/m1/s1

InChI key

VRYALKFFQXWPIH-PBXRRBTRSA-N

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Biochem/physiol Actions

2-Deoxy-D-Glucose (2-Deoxyglucose) is a glucose analog that inhibits glycolysis via its actions on hexokinase, the rate limiting step of glycolysis. It is phosphorylated by hexokinase to 2-DG-P which can not be further metabolized by phosphoglucose isomerase. This leads to the accumulation of 2-DG-P in the cell and the depletion in cellular ATP. In vitro, 2-Deoxyglucose has been shown to induce autophagy, increase ROS production, and activate AMPK.

Certificate of Analysis

Certificate of Origin

Kyoung-Jin Jang et al.
Nature communications, 6, 6750-6750 (2015-04-11)
During immune reactions, functionally distinct B-cell subsets are generated by stochastic processes, including class-switch recombination (CSR) and plasma cell differentiation (PCD). In this study, we show a strong association between individual B-cell fates and mitochondrial functions. CSR occurs specifically in...

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