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MedKoo Cat#: 596559 | Name: Diazooxonorleucine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Diazooxonorleucine is an amino acid that inhibits phosphate-activated glutaminase and interferes with glutamine metabolism. It is an antineoplastic antibiotic produced by an unidentified species of Streptomyces from Peruvian soil.

Chemical Structure

Diazooxonorleucine
CAS#157-03-9

Theoretical Analysis

MedKoo Cat#: 596559

Name: Diazooxonorleucine

CAS#: 157-03-9

Chemical Formula: C6H9N3O3

Exact Mass: 171.0644

Molecular Weight: 171.15

Elemental Analysis: C, 42.11; H, 5.30; N, 24.55; O, 28.04

Price and Availability

Size Price Availability Quantity
50mg USD 450.00 2 Weeks
100mg USD 750.00 2 Weeks
200mg USD 1,250.00 2 Weeks
500mg USD 2,250.00 2 Weeks
1g USD 3,250.00 2 Weeks
2g USD 5,850.00 2 Weeks
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Related CAS #
157-03-9
Synonym
Diazooxonorleucine; NSC 7365; NSC-7365; NSC7365; DON; L-DON
IUPAC/Chemical Name
(S)-2-amino-6-diazo-5-oxohexanoic acid
InChi Key
YCWQAMGASJSUIP-YFKPBYRVSA-N
InChi Code
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
SMILES Code
N[C@@H](CCC(C=[N+]=[N-])=O)C(O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 171.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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Structure of 6-diazo-5-oxo-norleucine-bound human gamma-glutamyl transpeptidase 1, a novel mechanism of inactivation. Protein Sci. 2017 Jun;26(6):1196-1205. doi: 10.1002/pro.3172. Epub 2017 Apr 17. PubMed PMID: 28378915; PubMed Central PMCID: PMC5441403. 4: Manivannan S, Baxter VK, Schultz KL, Slusher BS, Griffin DE. Protective Effects of Glutamine Antagonist 6-Diazo-5-Oxo-l-Norleucine in Mice with Alphavirus Encephalomyelitis. J Virol. 2016 Sep 29;90(20):9251-62. doi: 10.1128/JVI.01045-16. Print 2016 Oct 15. PubMed PMID: 27489275; PubMed Central PMCID: PMC5044826. 5: Griffin DE. Alphavirus Encephalomyelitis: Mechanisms and Approaches to Prevention of Neuronal Damage. Neurotherapeutics. 2016 Jul;13(3):455-60. doi: 10.1007/s13311-016-0434-6. Review. PubMed PMID: 27114366; PubMed Central PMCID: PMC4965404. 6: Xie S, Jin N, Gu J, Shi J, Sun J, Chu D, Zhang L, Dai CL, Gu JH, Gong CX, Iqbal K, Liu F. O-GlcNAcylation of protein kinase A catalytic subunits enhances its activity: a mechanism linked to learning and memory deficits in Alzheimer's disease. Aging Cell. 2016 Jun;15(3):455-64. doi: 10.1111/acel.12449. Epub 2016 Feb 3. PubMed PMID: 26840030; PubMed Central PMCID: PMC4854926. 7: Crunkhorn S. Infectious disease: Glutamine analogue reverses cerebral malaria. Nat Rev Drug Discov. 2015 Dec;14(12):820. doi: 10.1038/nrd4786. Epub 2015 Nov 20. PubMed PMID: 26585535. 8: Lee CF, Lo YC, Cheng CH, Furtmüller GJ, Oh B, Andrade-Oliveira V, Thomas AG, Bowman CE, Slusher BS, Wolfgang MJ, Brandacher G, Powell JD. Preventing Allograft Rejection by Targeting Immune Metabolism. Cell Rep. 2015 Oct 27;13(4):760-770. doi: 10.1016/j.celrep.2015.09.036. Epub 2015 Oct 17. PubMed PMID: 26489460; PubMed Central PMCID: PMC4626381. 9: Gordon EB, Hart GT, Tran TM, Waisberg M, Akkaya M, Kim AS, Hamilton SE, Pena M, Yazew T, Qi CF, Lee CF, Lo YC, Miller LH, Powell JD, Pierce SK. Targeting glutamine metabolism rescues mice from late-stage cerebral malaria. Proc Natl Acad Sci U S A. 2015 Oct 20;112(42):13075-80. doi: 10.1073/pnas.1516544112. Epub 2015 Oct 5. PubMed PMID: 26438846; PubMed Central PMCID: PMC4620853. 10: Cervantes-Madrid D, Romero Y, Dueñas-González A. Reviving Lonidamine and 6-Diazo-5-oxo-L-norleucine to Be Used in Combination for Metabolic Cancer Therapy. Biomed Res Int. 2015;2015:690492. doi: 10.1155/2015/690492. Epub 2015 Sep 6. Review. PubMed PMID: 26425550; PubMed Central PMCID: PMC4575731. 11: Goswami MT, Chen G, Chakravarthi BV, Pathi SS, Anand SK, Carskadon SL, Giordano TJ, Chinnaiyan AM, Thomas DG, Palanisamy N, Beer DG, Varambally S. Role and regulation of coordinately expressed de novo purine biosynthetic enzymes PPAT and PAICS in lung cancer. Oncotarget. 2015 Sep 15;6(27):23445-61. PubMed PMID: 26140362; PubMed Central PMCID: PMC4695129. 12: Cervantes-Madrid D, Dueñas-González A. Antitumor effects of a drug combination targeting glycolysis, glutaminolysis and de novo synthesis of fatty acids. Oncol Rep. 2015 Sep;34(3):1533-42. doi: 10.3892/or.2015.4077. Epub 2015 Jun 24. PubMed PMID: 26134042. 13: Cao BB, Huang Y, Jiang YY, Qiu YH, Peng YP. Cerebellar fastigial nuclear glutamatergic neurons regulate immune function via hypothalamic and sympathetic pathways. J Neuroimmune Pharmacol. 2015 Mar;10(1):162-78. doi: 10.1007/s11481-014-9572-y. Epub 2015 Feb 4. PubMed PMID: 25649846. 14: Potter MC, Baxter VK, Mathey RW, Alt J, Rojas C, Griffin DE, Slusher BS. Neurological sequelae induced by alphavirus infection of the CNS are attenuated by treatment with the glutamine antagonist 6-diazo-5-oxo-l-norleucine. J Neurovirol. 2015 Apr;21(2):159-73. doi: 10.1007/s13365-015-0314-6. Epub 2015 Feb 3. PubMed PMID: 25645378; PubMed Central PMCID: PMC4375032. 15: Olsen RR, Mary-Sinclair MN, Yin Z, Freeman KW. Antagonizing Bcl-2 family members sensitizes neuroblastoma and Ewing's sarcoma to an inhibitor of glutamine metabolism. PLoS One. 2015 Jan 23;10(1):e0116998. doi: 10.1371/journal.pone.0116998. eCollection 2015. PubMed PMID: 25615615; PubMed Central PMCID: PMC4304844. 16: Alt J, Potter MC, Rojas C, Slusher BS. Bioanalysis of 6-diazo-5-oxo-l-norleucine in plasma and brain by ultra-performance liquid chromatography mass spectrometry. Anal Biochem. 2015 Apr 1;474:28-34. doi: 10.1016/j.ab.2015.01.001. Epub 2015 Jan 10. PubMed PMID: 25584882; PubMed Central PMCID: PMC4357560. 17: Joseph D, Kimar C, Symington B, Milne R, Essop MF. The detrimental effects of acute hyperglycemia on myocardial glucose uptake. Life Sci. 2014 Jun 6;105(1-2):31-42. doi: 10.1016/j.lfs.2014.04.009. Epub 2014 Apr 18. PubMed PMID: 24747137. 18: Thangavelu K, Chong QY, Low BC, Sivaraman J. Structural basis for the active site inhibition mechanism of human kidney-type glutaminase (KGA). Sci Rep. 2014 Jan 23;4:3827. doi: 10.1038/srep03827. PubMed PMID: 24451979; PubMed Central PMCID: PMC4929687. 19: Takahashi N, Tarumi W, Ishizuka B. Involvement of hyaluronan synthesis in ovarian follicle growth in rats. Reproduction. 2013 Dec 19;147(2):189-97. doi: 10.1530/REP-13-0464. Print 2014 Feb. PubMed PMID: 24218629. 20: Erickson JR, Pereira L, Wang L, Han G, Ferguson A, Dao K, Copeland RJ, Despa F, Hart GW, Ripplinger CM, Bers DM. Diabetic hyperglycaemia activates CaMKII and arrhythmias by O-linked glycosylation. Nature. 2013 Oct 17;502(7471):372-6. doi: 10.1038/nature12537. Epub 2013 Sep 29. PubMed PMID: 24077098; PubMed Central PMCID: PMC3801227.