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D2141

Sigma-Aldrich

6-Diazo-5-oxo-L-norleucine

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

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C6H9N3O3
Número CAS:
Peso molecular:
171.15
Beilstein:
1725815
Número MDL:
Código UNSPSC:
12352209
ID de substância PubChem:
NACRES:
NA.26

Nome do produto

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

Ensaio

>95% (TLC)

Nível de qualidade

Formulário

crystalline

técnica(s)

ligand binding assay: suitable

cor

light yellow

pf

145 °C

espectro de atividade do antibiótico

neoplastics

Modo de ação

enzyme | inhibits

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

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

chave InChI

YCWQAMGASJSUIP-YFKPBYRVSA-N

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Descrição geral

Chemical structure: amino acid derivatives

Aplicação

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

Ações bioquímicas/fisiológicas

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.

Pictogramas

Skull and crossbones

Palavra indicadora

Danger

Frases de perigo

Classificações de perigo

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

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

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


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P Freund et al.
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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.

Artigos

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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