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D2141

Sigma-Aldrich

6-Diazo-5-oxo-L-norleucine

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

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C6H9N3O3
Numero CAS:
157-03-9
Peso molecolare:
171.15
Beilstein:
1725815
Numero MDL:
MFCD00037218
Codice UNSPSC:
12352209
ID PubChem:
24893639
NACRES:
NA.26

Nome del prodotto

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

Saggio

>95% (TLC)

Livello qualitativo

200

Stato

crystalline

tecniche

ligand binding assay: suitable

Colore

light yellow

Punto di fusione

145 °C

Spettro attività antibiotica

neoplastics

Modalità d’azione

enzyme | inhibits

Temperatura di conservazione

−20°C

Stringa SMILE

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
YCWQAMGASJSUIP-YFKPBYRVSA-N

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Descrizione generale

Chemical structure: amino acid derivatives

Applicazioni

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

Azioni biochim/fisiol

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.

Pittogrammi

Skull and crossbones
GHS06

Avvertenze

Danger

Indicazioni di pericolo

H301 + H311 + H331

Classi di pericolo

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Codice della classe di stoccaggio

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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

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Certificati d'analisi (COA)

Lot/Batch Number
069M4084V
029M4072V
108M4013V
038M4008V
107M4026V

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TIC10 angular ≥98% (HPLC)

Sigma-Aldrich

SML1068

TIC10 angular

Glutaminase Inhibitor, Compound 968 Glutaminase Inhibitor, Compd 968, is a cell-permeable, reversible inhibitor of mitochondrial glutaminase. Represses growth & invasive activity in glutaminase upregulated fibroblasts and tumor cells.

Sigma-Aldrich

352010

Glutaminase Inhibitor, Compound 968

OSMI-1 ≥98% (HPLC)

Sigma-Aldrich

SML1621

OSMI-1

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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Articoli

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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