Molecular structure of 6-Diazo-5-oxo-L-norleucine, CAS Number: 157-03-9
6-Diazo-5-oxo-L-norleucine (CAS 157-03-9)
Alternate Names:
DON
Application:
6-Diazo-5-oxo-L-norleucine is a glutamine analogue
CAS Number:
157-03-9
Purity:
≥95%
Molecular Weight:
171.15
Molecular Formula:
C6H9N3O3
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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Description
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SDS & Certificate of Analysis
6-Diazo-5-oxo-L-norleucine serves as an influential inhibitor targeting enzymes that utilize glutamine, such as glutaminase and amidotransferases. The compound achieves its inhibitory effect by irreversibly binding to the enzymes′ active sites, thus shutting down critical aspects of glutamine metabolism. This inhibition has broad ramifications on several key cellular processes, particularly those involved in nucleotide and protein synthesis, as well as in energy production. As glutamine plays a central role in cellular metabolism, the interruption of its utilization offers experimental avenue for dissecting the metabolic pathways to cell growth and maintenance. The mechanism by which 6-Diazo-5-oxo-L-norleucine operates provides significant insights into cellular metabolic dependencies.
6-Diazo-5-oxo-L-norleucine (CAS 157-03-9) References
- Antiviral effect of 6-diazo-5-oxo-L-norleucine, antagonist of gamma-glutamyl transpeptidase, on replication of human parainfluenza virus type 2. | Nishio, M., et al. 1990. J Gen Virol. 71 (Pt 1): 61-7. PMID: 1968085
- Bioanalysis of 6-diazo-5-oxo-l-norleucine in plasma and brain by ultra-performance liquid chromatography mass spectrometry. | Alt, J., et al. 2015. Anal Biochem. 474: 28-34. PMID: 25584882
- Protective Effects of Glutamine Antagonist 6-Diazo-5-Oxo-l-Norleucine in Mice with Alphavirus Encephalomyelitis. | Manivannan, S., et al. 2016. J Virol. 90: 9251-62. PMID: 27489275
- Discovery of 6-Diazo-5-oxo-l-norleucine (DON) Prodrugs with Enhanced CSF Delivery in Monkeys: A Potential Treatment for Glioblastoma. | Rais, R., et al. 2016. J Med Chem. 59: 8621-33. PMID: 27560860
- Feasibility and antitumor efficacy in vivo, of simultaneously targeting glycolysis, glutaminolysis and fatty acid synthesis using lonidamine, 6-diazo-5-oxo-L-norleucine and orlistat in colon cancer. | Cervantes-Madrid, D., et al. 2017. Oncol Lett. 13: 1905-1910. PMID: 28454342
- Evaluation of genetic toxicity of 6-diazo-5-oxo-l-norleucine (DON). | Kulkarni, RM., et al. 2017. Toxicol Mech Methods. 27: 518-527. PMID: 28552037
- Tumor-Targeted Delivery of 6-Diazo-5-oxo-l-norleucine (DON) Using Substituted Acetylated Lysine Prodrugs. | Tenora, L., et al. 2019. J Med Chem. 62: 3524-3538. PMID: 30892035
- Transient meiotic arrest maintained by DON (6-diazo-5-oxo-l-norleucine) enhances nuclear/cytoplasmic maturation of porcine oocytes. | Yang, HJ., et al. 2019. Reproduction. 158: 543-554. PMID: 31652418
- L-asparaginase and 6-diazo-5-oxo-L-norleucine synergistically inhibit the growth of glioblastoma cells. | Ohba, S. and Hirose, Y. 2020. J Neurooncol. 146: 469-475. PMID: 32020477
- Complete Biosynthetic Pathway of Alazopeptin, a Tripeptide Consisting of Two Molecules of 6-Diazo-5-oxo-l-norleucine and One Molecule of Alanine. | Kawai, S., et al. 2021. Angew Chem Int Ed Engl. 60: 10319-10325. PMID: 33624374
- Gluconeogenic enzyme PCK1 deficiency promotes CHK2 O-GlcNAcylation and hepatocellular carcinoma growth upon glucose deprivation. | Xiang, J., et al. 2021. J Clin Invest. 131: PMID: 33690219
- Model studies towards prodrugs of the glutamine antagonist 6-diazo-5-oxo-l-norleucine (DON) containing a diazo precursor. | Gao, RD., et al. 2021. Bioorg Med Chem Lett. 50: 128321. PMID: 34400301
- Targeting Glutamine Metabolism Ameliorates Autoimmune Hepatitis via Inhibiting T Cell Activation and Differentiation. | Yu, Q., et al. 2022. Front Immunol. 13: 880262. PMID: 35663990
- Inactivation of rat renal phosphate-dependent glutaminase with 6-diazo-5-oxo-L-norleucine. Evidence for interaction at the glutamine binding site. | Shapiro, RA., et al. 1979. J Biol Chem. 254: 2835-8. PMID: 429321
- Enhancement of antitumor activity of glutamine antagonists 6-diazo-5-oxo-L-norleucine and acivicin in cell culture by glutaminase-asparaginase. | Rosenfeld, H. and Roberts, J. 1981. Cancer Res. 41: 1324-8. PMID: 7214322
Inhibitor of:
γ-GCSc, ASCT2, AsnRS, ASNSD1, Asparagine synthetase, ASPG, biotinidase, calicin, CPS1, CTP, CTPS2, CTU2, GCAT, GCL, GFAT1, GFAT2, GGL, Gl Syn, GLULD1, GLYATL3, GNA1, GNPDA1, GNPDA2, GOT1L1, KGA_Gls, Mpi, NAG, O-GlcNAc transferase, PSAT1, PUS7L, QAPRTase, RhBG, SPINDLY, THNSL2, Trp E, UAP1L1, UROC1, and XylT-II.Activator of:
C3orf64, CPS2, CTP Synthase 1, EP58, and P5CR.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
6-Diazo-5-oxo-L-norleucine, 5 mg | sc-227078 | 5 mg | $88.00 | |||
6-Diazo-5-oxo-L-norleucine, 25 mg | sc-227078A | 25 mg | $291.00 | |||
6-Diazo-5-oxo-L-norleucine, 100 mg | sc-227078B | 100 mg | $926.00 | |||
6-Diazo-5-oxo-L-norleucine, 250 mg | sc-227078C | 250 mg | $2195.00 |