D4601
2-Deoxy-D-glucose
99%
Synonym(s):
2-Deoxy-D-arabinohexose
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About This Item
Empirical Formula (Hill Notation):
C6H12O5
CAS Number:
Molecular Weight:
164.16
EC Number:
205-823-0
UNSPSC Code:
12352103
MDL number:
Beilstein/REAXYS Number:
1723331
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
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.
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Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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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