| Identification | Back Directory | [Name]
6-DIAZO-5-OXO-L-NORLEUCINE | [CAS]
157-03-9 | [Synonyms]
DON
L-DON
D2141
NSC-7365
H-L-Don-OH
don(pharmaceutical)
diazo-oxo-norleucine
H-6-DIAZO-5-OXO-NLE-OH
H-NLE(6-DIAZO-5-OXO)-OH
L-Nle(6-Diazo-5-oxo)-OH
6-DIAZO-5-OXO-NORLEUCINE
6-diazo-5-oxo,l-norleucin
6-diazo-5-oxo-l-norleucin
L-6-Diazo-5-oxonorleucine
5-Oxo-6-diazo-L-norleucine
6-DIAZO-5-OXO-L-NORLEUCINE
H-6-DIAZO-5-OXO-L-NORLEUCINE
L-Norleucine, 6-diazo-5-oxo-
6-DIAZO-5-OXO-L-NORLEUCINE USP/EP/BP
6-DIAZO-5-OXO-L-2-AMINOHEXANOIC ACID
(S)-2-AMINO-6-DIAZO-5-OXOCAPROIC ACID
6-Diazo-5-oxo-L-norleucine crystalline
(S)-2-aMino-6-diazo-5-oxohexanoic acid
(2S)-2-amino-6-diazo-5-oxohexanoic acid
(S)-2-Amino-6-diazo-5-oxocaproic acid, DON
6-Diazo-5-oxo-L-norleucine≥ 99% (TBAH, Titration)
(S)-2-Amino-6-diazo-5-oxocaproic acid, (S)-6-Diazo-5-oxo-L-norleucine
L-DON, 6-Diazo-5-oxo-L-2-aMinohexanoic acid, H-Glu(diazoMethylketone)-OH | [EINECS(EC#)]
251-228-4 | [Molecular Formula]
C6H9N3O3 | [MDL Number]
MFCD00037218 | [MOL File]
157-03-9.mol | [Molecular Weight]
171.15 |
| Chemical Properties | Back Directory | [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| |
| Hazard Information | Back Directory | [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.] |
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