D2141
6-Diazo-5-oxo-L-norleucine
≥95% (HPLC), suitable for ligand binding assays
Synonym(s):
(S)-2-Amino-6-diazo-5-oxocaproic acid, DON
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About This Item
Empirical Formula (Hill Notation):
C6H9N3O3
CAS Number:
Molecular Weight:
171.15
NACRES:
NA.26
PubChem Substance ID:
UNSPSC Code:
12352209
MDL number:
Beilstein/REAXYS Number:
1725815
Product Name
6-Diazo-5-oxo-L-norleucine, powder
assay
≥95% (HPLC)
Quality Level
form
powder
technique(s)
ligand binding assay: suitable
color
faint yellow, to yellow or tan
antibiotic activity spectrum
neoplastics
mode of action
enzyme | inhibits
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
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 used to study mechanisms of glutamine utilizing enzymes such as carbamoyl phosphate synthase and cytidine triphosphate synthase.
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.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
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Brandon T Pfannenstiel et al.
Biotechnology advances, 37(6), 107345-107345 (2019-02-10)
Fungi produce an abundance of bioactive secondary metabolites which can be utilized as antibiotics and pharmaceutical drugs. The genes encoding secondary metabolites are contiguously arranged in biosynthetic gene clusters (BGCs), which supports co-regulation of all genes required for any one
P Freund et al.
Leukemia, 31(10), 2132-2142 (2017-01-12)
The signal transducer and activator of transcription 5 (STAT5) regulates differentiation, survival, proliferation and transformation of hematopoietic cells. Upon cytokine stimulation, STAT5 tyrosine phosphorylation (pYSTAT5) is transient, while in diverse neoplastic cells persistent overexpression and enhanced pYSTAT5 are frequently found.
Laura M Shelton et al.
International journal of cancer, 127(10), 2478-2485 (2010-05-18)
Metastatic cancer is a major cause of morbidity and mortality. Current therapeutic options consist of chemotherapy, radiation or targeted therapies. However, these therapies are often toxic, effective over a small range of cancer types or result in drug resistance. Therefore