6-DIAZO-5-OXO-L-NORLEUCINE Basic information
Product Name: 6-DIAZO-5-OXO-L-NORLEUCINE
Synonyms: 6-diazo-5-oxo,l-norleucin;6-diazo-5-oxo-l-norleucin;diazo-oxo-norleucine;don(pharmaceutical);6-DIAZO-5-OXO-L-2-AMINOHEXANOIC ACID;6-DIAZO-5-OXO-L-NORLEUCINE;6-DIAZO-5-OXO-NORLEUCINE;L-DON
CAS: 157-03-9
MF: C6H9N3O3
MW: 171.15
EINECS: 251-228-4
Product Categories: Antibiotics
Mol File: 157-03-9.mol
6-DIAZO-5-OXO-L-NORLEUCINE Structure
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 Information
Provider Language
SigmaAldrich English
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.]