Skip to Content
MilliporeSigma
All Photos(1)

Documents

D2141

Sigma-Aldrich

6-Diazo-5-oxo-L-norleucine

>95% (TLC), suitable for ligand binding assays

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C6H9N3O3
CAS Number:
157-03-9
Molecular Weight:
171.15
Beilstein/REAXYS Number:
1725815
MDL number:
MFCD00037218
UNSPSC Code:
12352209
PubChem Substance ID:
24893639
NACRES:
NA.26

product name

6-Diazo-5-oxo-L-norleucine, crystalline

assay

>95% (TLC)

Quality Level

200

form

crystalline

technique(s)

ligand binding assay: suitable

color

light yellow

mp

145 °C

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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.

pictograms

Skull and crossbones
GHS06

signalword

Danger

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Yingyue Zhang et al.
Journal of agricultural and food chemistry, 67(30), 8411-8418 (2019-06-28)
Economic loss of postharvest wheat under poor storage conditions due to fungal spoilage and mycotoxin contamination is severe. In order to study the influencing factors of the aggravation of mildew in natural wheat during storage, we assessed changes in Fusarium
Sen-Ling Feng et al.
Journal of ginseng research, 44(2), 247-257 (2020-03-10)
Multidrug resistance (MDR) to chemotherapy drugs remains a major challenge in clinical cancer treatment. Here we investigated whether and how ginsenoside Rg5 overcomes the MDR mediated by ABCB1 transporter in vitro and in vivo. Cytotoxicity and colon formation as well as the
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
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.
View All Related Papers

Articles

Glutamine Metabolism in Cancer Cells

Sigma article discusses tumor cell metabolic pathways, focusing on aerobic glycolysis and mitochondrial activity.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service