828919-20-6 Usage
Description
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(1Z)-2-(2,4-dinitrophenyl)ethenyl]-8-oxo-7-[(2-thienylacetyl)amino]-, (4-methoxyphenyl)methyl ester, (6R,7R)is a complex organic compound that serves as an intermediate in the synthesis of Nitrocefin (N493815), a chromogenic β-lactamase substrate. 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,
3-[(1Z)-2-(2,4-dinitrophenyl)ethenyl]-8-oxo-7-[(2-thienylacetyl)amino]-,
(4-methoxyphenyl)methyl ester, (6R,7R)is characterized by its unique molecular structure, which includes a thia-azabicyclo ring, a 2,4-dinitrophenyl ethenyl group, and a thienylacetylamino moiety.
Uses
Used in Detection of β-lactamase Activity:
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(1Z)-2-(2,4-dinitrophenyl)ethenyl]-8-oxo-7-[(2-thienylacetyl)amino]-, (4-methoxyphenyl)methyl ester, (6R,7R)is used as an intermediate in the synthesis of Nitrocefin, a chromogenic β-lactamase substrate. Nitrocefin undergoes a color change from yellow to red when the amide bond in the β-lactam ring is hydrolyzed by β-lactamase enzymes. This color change is utilized for the detection of β-lactamase activity from bacterial cell extracts by isoelectric focusing and spectroscopy.
Used in Studies Involving β-lactamase Resistant Antibiotics:
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(1Z)-2-(2,4-dinitrophenyl)ethenyl]-8-oxo-7-[(2-thienylacetyl)amino]-, (4-methoxyphenyl)methyl ester, (6R,7R)is also used in studies involving β-lactamase resistant antibiotics. The color changing properties of Nitrocefin, which is synthesized using this compound as an intermediate, allow for the investigation of β-lactamase activity and the development of new antibiotics that can overcome resistance mechanisms in bacteria.
Check Digit Verification of cas no
The CAS Registry Mumber 828919-20-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,2,8,9,1 and 9 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 828919-20:
(8*8)+(7*2)+(6*8)+(5*9)+(4*1)+(3*9)+(2*2)+(1*0)=206
206 % 10 = 6
So 828919-20-6 is a valid CAS Registry Number.
828919-20-6Relevant articles and documents
A practical synthesis of nitrocefin
Lee, Mijoon,Hesek, Dusan,Mobashery, Shahriar
, p. 367 - 369 (2005)
(Chemical Equation Presented). Nitrocefin is a key reagent for high and low throughput assays of the activities of penicillin-binding proteins (PBPs) and β-lactamases, the former used for discovery of antibiotics and the latter for inhibitors of resistance determinants for β-lactam antibiotics. This compound is commercially available but is prohibitively expensive because of the circuitous routes to its synthesis. We describe herein a three-step synthesis of nitrocefin that gives an overall yield of 44%. This is a practical route to the synthesis of this key reagent for drug discovery.
