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D2141

Sigma-Aldrich

6-Diazo-5-oxo-L-norleucine

crystalline

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:
157-03-9
Molecular Weight:
171.15
Beilstein/REAXYS Number:
1725815
MDL number:
MFCD00037218
UNSPSC Code:
12352209
PubChem Substance ID:
24893639
NACRES:
NA.26

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

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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’.

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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.
A novel nitrate/nitrite permease in the marine Cyanobacterium synechococcus sp. strain PCC 7002.
Sakamoto T
Journal of Bacteriology, 181(23), 7363-7372 (1999)
The rediscovery of DON (6-diazo-5-oxo-L-norleucine).
Kisner DL
Recent Results in Cancer Research. Fortschritte der Krebsforschung. Progres Dans Les Recherches Sur le Cancer, 74, 258-263 (1980)
María M E Belizán et al.
International journal of food microbiology, 305, 108242-108242 (2019-06-10)
Fusarium meridionale and F. boothii cause Gibberella Ear Rot (GER) in maize. This study determined the effects of temperature (5-35 °C) and water activity (0.90-0.995 aw) on the growth, and deoxynivalenol (DON) and nivalenol (NIV) production of F. meridionale and F.
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Glutamine Metabolism is Dysregulated in Many Cancer Cells

Sigma-Aldrich presents an article about how 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 metabolites away from mitochondrial oxidative phosphorylation, many tumor cells exhibit increased mitochondrial activity.

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