6-DIAZO-5-OXO-L-NORLEUCINE Chemical Properties

Melting point:

145 °C

Boiling point:

301.12°C (rough estimate)

Density 

1.3994 (rough estimate)

refractive index 

1.5800 (estimate)

storage temp. 

-20°C

solubility 

DMSO (Slightly, Heated, Sonicated), Water (Slightly)

form 

crystalline

color 

light yellow

Merck 

13,3026

BRN 

1725815

Stability:

Hygroscopic

InChI

InChI=1/C6H9N3O3/c7-5(6(11)12)2-1-4(10)3-9-8/h3,5H,1-2,7H2,(H,11,12)/t5-/s3

InChIKey

YCWQAMGASJSUIP-GQMHJJTINA-N

SMILES

C(C(=O)C=[N+]=[N-])C[C@H](N)C(=O)O |&1:7,r|

Safety Information

Hazard Codes 

T

Risk Statements 

23/24/25

Safety Statements 

36/37/39-45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

RC6340000

F 

8

MSDS

• Language:English Provider:SigmaAldrich

6-DIAZO-5-OXO-L-NORLEUCINE Usage And Synthesis

Chemical Properties

Slightly yellow powder

Uses

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

Definition

ChEBI: 6-diazo-5-oxo-L-norleucine is a non-proteinogenic L-alpha-amino acid that is L-norleucine which is substituted at position 5 by an oxo group and at position 6 by a diazo group. It is as inhibitor of various glutamine-utilising enzymes. It has a role as a bacterial metabolite, an analgesic, an antibacterial agent, an antiviral agent, an antineoplastic agent, an EC 6.3.5.5 [carbamoyl-phosphate synthase (glutamine-hydrolysing)] inhibitor, an EC 6.3.4.2 [CTP synthase (glutamine hydrolyzing)] inhibitor, an EC 6.3.5.3 (phosphoribosylformylglycinamidine synthase) inhibitor, an EC 6.3.5.2 [GMP synthase (glutamine-hydrolysing)] inhibitor, an antimetabolite, a glutamine antagonist, an apoptosis inducer, an EC 2.4.2.14 (amidophosphoribosyltransferase) inhibitor, an EC 3.5.1.2 (glutaminase) inhibitor, an EC 6.3.5.1 [NAD(+) synthase (glutamine-hydrolysing)] inhibitor and an EC 6.3.5.4 [asparagine synthase (glutamine-hydrolysing)] inhibitor. It is a non-proteinogenic L-alpha-amino acid, a diazo compound and a ketone. It is a tautomer of a 6-diazo-5-oxo-L-norleucine zwitterion.

General Description

Chemical structure: amino acid derivatives

Biochem/physiol Actions

DON is used to study mechanisms of glutamine utilizing enzymes such as carbamoyl phosphate synthase and cytidine triphosphate synthase.

Purification Methods

Crystallise it from EtOH, H2O/EtOH, MeOH, 95% aqueous MeOH or H2O/Me2CO. [DeWald & Moor J Am Chem Soc 80 3944 1958, Dion et al. J Am Chem Soc 78 3075 1956, Beilstein 4 IV 3278.]

6-DIAZO-5-OXO-L-NORLEUCINE(157-03-9)Related Product Information

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