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Merck

D2141

6-Diazo-5-oxo-L-norleucine

≥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

Product Name

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

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

SMILES string

N[C@@H](CCC(=O)C=[N+]=[N-])C(O)=O

InChI key

YCWQAMGASJSUIP-YFKPBYRVSA-N

assay

≥95% (HPLC)

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

Quality Level

200

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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.

General description

Chemical structure: amino acid derivatives

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000474367
0000474368
0000474367
0000474368
0000371455

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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
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
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
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.
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)
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