6-DIAZO-5-OXO-L-NORLEUCINE
Synonym(s):(S)-2-Amino-6-diazo-5-oxocaproic acid;DON
- CAS NO.:157-03-9
- Empirical Formula: C6H9N3O3
- Molecular Weight: 171.15
- MDL number: MFCD00037218
- EINECS: 251-228-4
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-21 15:02:00
What is 6-DIAZO-5-OXO-L-NORLEUCINE?
Chemical properties
Slightly yellow powder
The Uses of 6-DIAZO-5-OXO-L-NORLEUCINE
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.]
Properties of 6-DIAZO-5-OXO-L-NORLEUCINE
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 |
Safety information for 6-DIAZO-5-OXO-L-NORLEUCINE
Signal word | Danger |
Pictogram(s) |
Skull and Crossbones Acute Toxicity GHS06 |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
Computed Descriptors for 6-DIAZO-5-OXO-L-NORLEUCINE
New Products
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