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D2141

6-Diazo-5-oxo-L-norleucine

Name: 6-Diazo-5-oxo-<SC>L</SC>-norleucine
Brand: SIGMA

≥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:

157-03-9

Molecular Weight:

171.15

NACRES:

NA.26

PubChem Substance ID:

24893639

UNSPSC Code:

12352209

MDL number:

MFCD00037218

Beilstein/REAXYS Number:

1725815

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Product Name

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

assay

≥95% (HPLC)

Quality Level

200

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

Related Categories

Biochemicals

Cell Culture Supplements & Reagents

Amino Acids – Building Blocks of Life Science

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

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.

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.

pictograms

GHS06

signalword

Danger

hcodes

H301 + H311 + H331

pcodes

P261 - P264 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311

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

Regulatory Information

涉药品监管产品

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Certificates of Analysis (COA)

Lot/Batch Number

0000530573

0000474367

0000474368

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Interactions among Fungal Community, Fusarium Mycotoxins, and Components of Harvested Wheat under Simulated Storage Conditions.

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

Glutamine targeting inhibits systemic metastasis in the VM-M3 murine tumor model.

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

Ginsenoside Rg5 overcomes chemotherapeutic multidrug resistance mediated by ABCB1 transporter: in vitro and in vivo study.

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

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)

A novel nitrate/nitrite permease in the marine Cyanobacterium synechococcus sp. strain PCC 7002.

Sakamoto T

Journal of Bacteriology, 181(23), 7363-7372 (1999)

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Global Trade Item Number

SKU	GTIN
D2141-25MG	04061833561690
D2141-5MG	04061833561706

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