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D2141 Sigma-Aldrich

6-Diazo-5-oxo-L-norleucine

crystalline

Synonym: (S)-2-Amino-6-diazo-5-oxocaproic acid, DON

  • CAS Number 157-03-9

  • Empirical Formula (Hill Notation) C6H9N3O3

  • Molecular Weight 171.15

  •  Beilstein/REAXYS Number 1725815

  •  MDL number MFCD00037218

  •  PubChem Substance ID 24893639

  •  NACRES NA.26

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Properties

Related Categories A - K, Amino Acid Derivatives, Antibacterial, Antibiotics, Antibiotics A to Z,
Quality Level   200
assay   >95% (TLC)
form   crystalline
application(s)   ligand binding assay: suitable
color   light yellow
mp   145 °C
Mode of action   enzyme | inhibits
antibiotic activity spectrum   neoplastics
storage temp.   −20°C
SMILES string   N[C@@H](CCC(=O)C=[N+]=[N-])C(O)=O
InChI   1S/C6H9N3O3/c7-5(6(11)12)2-1-4(10)3-9-8/h3,5H,1-2,7H2,(H,11,12)/t5-/m0/s1
InChI key   YCWQAMGASJSUIP-YFKPBYRVSA-N

Description

General description

Chemical structure: amino acid derivatives

Application

6-Diazo-5-oxo-L-norleucine (DON) has been used as an inhibitor of glutamine synthetase–glutamine(amide)-2-oxoglutarate aminotransferase.

Biochem/physiol Actions

6-Diazo-5-oxo-L-norleucine (DON), a glutamine analogue, is used as an inhibitor to study the function, specificity and characteristics of cytidine triphosphate synthase 1(s) (CTPS1) and various glutaminase(s). DON is used to inhibit glutamine (GLN) flux between cells.

DON is associated with a number of reactions involving L-glutamine as a nitrogen source, such as nucleic acid and protein synthesis. It is known to possess anticancer activity against choriocarcinoma.

DON is used to study mechanisms of glutamine utilizing enzymes such as carbamoyl phosphate synthase and cytidine triphosphate synthase.

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
WGK 3
RTECS 
RC6340000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Glutamine Metabolism is Dysregulated in Many Cancer Cells

Proliferatively active cells require both a source of carbon and of nitrogen for the synthesis of macromolecules. Although a large proportion of tumor cells utilize aerobic glycolysis and shunt metab...
BioFiles v7 n4
Keywords: Aerobic, Cancer, Citric Acid Cycle, Gene expression, Glycolysis, Metabolism, Metabolites, Phosphorylations, Transcription

Peer-Reviewed Papers
15

References

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92210 Timestrip Plus 0 °C
06693 Timestrip Plus -20 °C

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