6-Diazo-5-oxo-L-nor-Leucine

Category	Influenza Virus
CAS	157-03-9
Description	It is produced by the strain of Streptomyces ambofaciens. It has anti-tumor activity and is not suitable for clinical use due to excessive toxicity. Its N-acetyl (Duazomycin) also has anti-tumor effect.

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Synonyms	6-diazo-5-oxo-L-norleucine;157-03-9;diazooxonorleucine;L-DON;L-Norleucine, 6-diazo-5-oxo-;6-Diazo-5-oxo-L-nor-Leucine;DON;NSC-7365;(S)-2-Amino-6-diazo-5-oxocaproic acid;03J0H273KZ;MFCD00037218;DON (pharmaceutical);L-Norleucine,6-diazo-5-oxo-;H-6-Diazo-5-oxo-Nle-OH;NSC 7365;L-6-Diazo-5-oxonorleucine;BRN 1725815;Norleucine,6-diazo-5-oxo-;NSC7365;UNII-03J0H273KZ;AI3-26441;Norleucine, 6-diazo-5-oxo, L-;NCIMech_000302;NCIStruc1_000220;NCIStruc2_000175;(L)-DON;4-04-00-03278 (Beilstein Handbook Reference);CHEMBL97485;CHEMBL4303391;Diazo-5-oxo-L-norleucine, 6-;L-DON;H-Glu(diazomethylketone)-OH;6-Diazo-5-oxo-L-2-aminohexanoic acid;SCHEMBL15349013;SCHEMBL15349015;KMX-010;NCI7365;CHEBI:138889;YCWQAMGASJSUIP-YFKPBYRVSA-N;DTXSID501028846;EX-A1965;CCG-35449;CCG-37571;NCGC00013078;NSC823855;AKOS030213039;NSC-823855;NCGC00013078-02;NCGC00096202-01;6-Diazo-5-oxo-L-norleucine, crystalline;6-DIAZO-5-OXO-L-NORLEUCINE [MI];(2S)-2-amino-6-diazo-5-oxohexanoic acid;HY-108357;(2S)-2-amino-6-diazo-5-oxo-hexanoic acid;CS-0028442;NS00011811;C22429;F82153;A936514;Q245487;J-009370;
IUPAC Name	(2S)-2-amino-6-diazo-5-oxohexanoic acid
Molecular Weight	171.15
Molecular Formula	C6H9N3O3
Canonical SMILES	N[C@@H](CCC(C=[N+]=[N-])=O)C(O)=O
InChI	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
InChIKey	YCWQAMGASJSUIP-YFKPBYRVSA-N
Boiling Point	301.12°C (rough estimate)
Melting Point	142-150 °C
Purity	95%
Density	1.3994 g/cm3(rough estimate)
Solubility	Soluble in Water
Appearance	Solid
Application	Antibiotics, Antineoplastic
Storage	-20°C, sealed storage, away from moisture *In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)
Complexity	232
Exact Mass	228.08600
In Vitro	6-Diazo-5-oxo-L-nor-Leucine (DON) (0.3 mM; 1 h) shows inhibition of glutamine catabolism in WI-L2 cells, and decreases the selfrenewal potential and metastatic ability of tumor cell.
In Vivo	6-Diazo-5-oxo-L-nor-Leucine sensitizes pancreatic tumors to anti-PD1 resulting in tumor regression and prolonged survival in vivo. It also decreases hyaluronan and collagen in the tumor microenvironment, leading to an extensive remodeling of the ECM (extensive extracellular matrix), and an increases infiltration CD8+ T-cells.
PSA	147.12000
Target	Glutaminase; Bacterial; Influenza Virus; Antibiotic
XLogP3-AA	-3.5