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D2141

Sigma-Aldrich

6-Diazo-5-oxo-L-norleucine

crystalline

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Synonym(s):
(S)-2-Amino-6-diazo-5-oxocaproic acid, DON
Empirical Formula (Hill Notation):
C6H9N3O3
CAS Number:
Molecular Weight:
171.15
Beilstein/REAXYS Number:
1725815
MDL number:
PubChem Substance ID:
NACRES:
NA.26

assay

>95% (TLC)

Quality Level

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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1 of 4

This Item
B8385C3909C6880
6-Diazo-5-oxo-L-norleucine crystalline

D2141

6-Diazo-5-oxo-L-norleucine

Bestatin hydrochloride ≥98% (HPLC)

B8385

Bestatin hydrochloride

D-Cycloserine synthetic

C3909

D-Cycloserine

D-Cycloserine

C6880

D-Cycloserine

technique(s)

ligand binding assay: suitable

technique(s)

-

technique(s)

-

technique(s)

-

assay

>95% (TLC)

assay

≥98% (HPLC)

assay

-

assay

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Quality Level

200

Quality Level

-

Quality Level

-

Quality Level

-

mp

145 °C

mp

216 °C

mp

147 °C (dec.) (lit.)

mp

147 °C (dec.) (lit.)

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

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


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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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