157-03-9 Usage
Description
6-Diazo-5-oxo-L-norleucine (DON) is an amino acid derivative characterized by its slightly yellow powder form. It is a chemical compound with a unique structure that has garnered interest in various scientific and medical applications due to its specific properties and interactions.
Uses
Used in Pharmaceutical Industry:
6-Diazo-5-oxo-L-norleucine is used as an inhibitor for glutamine synthetase–glutamine(amide)-2-oxoglutarate aminotransferase. This application is significant because it plays a crucial role in the regulation of nitrogen metabolism and has been linked to various diseases, including cancer. By inhibiting this enzyme, DON can potentially be used in the development of therapeutic strategies to target these diseases.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 157-03-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,5 and 7 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 157-03:
(5*1)+(4*5)+(3*7)+(2*0)+(1*3)=49
49 % 10 = 9
So 157-03-9 is a valid CAS Registry Number.
InChI:InChI=1/C6H9N3O3/c7-5(6(11)12)2-1-4(10)3-9-8/h3,5H,1-2,7H2,(H-,10,11,12)/b4-3+/t5-/m0/s1
157-03-9Relevant articles and documents
Inhibition of Escherichia coli glucosamine synthetase by novel electrophilic analogues of glutamine - Comparison with 6-diazo-5-oxo-norleucine
Walker, Brian,Brown, Martin F.,Lynas, John F.,Martin,McDowell, Andrew,Badet, Bernard,Hill, Alan J.
, p. 2795 - 2798 (2000)
A series of electrophilic glutamine analogues based on 6-diazo-5-oxo-norleucine has been prepared, using novel synthetic routes, and evaluated as inhibitors of Escherichia coli. glucosamine synthetase. The γ-dimethylsulphonium salt analogue of glutamine was found to be one of the most potent inactivators of this enzyme yet reported, with an apparent second order rate constant (k2/K(i)) of 3.5 x 105 M-1 min-1. (C) 2000 Elsevier Science Ltd.
The Reaction of Lithium Trimethylsilyldiazomethane with Pyroglutamates - a Facile Synthesis of 6-Diazo-5-oxo-norleucine and Derivatives
Coutts, Ian G. C.,Saint, Robert E.
, p. 3242 - 3246 (2007/10/03)
The reaction of carbamate derivatives of pyroglutamic acid esters with the lithium salt of trimethylsilyldiazomethane below -100 deg C gives good yields of the corresponding substituted 6-diazo-5-oxo-norleucine esters; cleavage of Fmoc-substituted products provides a safe, convenient route to the parent acid.