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Preparation of Carbon-14 Labeled 2-(2-mercaptoacetamido)-3-phenylpropanoic Acid as Metallo-beta-lactamases Inhibitor (MBLI), for Coadministration with Beta-lactam Antibiotics

Author(s):

Ali Maleki*, Reza Taheri-Ledari, Reza Eivazzadeh-Keihan, Miguel de la Guardia and Ahad Mokhtarzadeh   Pages 1 - 7 ( 7 )

Abstract:


Numerous strategies are being executed to enter hazardous chemical materials into synthetic processes, with more convenience. In this regard, this paper presents a synthetic route for carbon-14 labeled 2-(2-mercaptoacetamido)-3-phenylpropanoic acid as a model inhibitor of metallo-β-lactamase enzyme to trace the mechanism of action of this compound in the body’s internal environment. Metallo-β-lactamase enzymes are produced by bacteria and are responsible for their resistance to β-lactam antibiotics. We report on our efforts to design a convenient synthetic pathway for preparation of carbon-14 labeled 2-(2-mercaptoacetamido)-3-phenylpropanoic acid via radioactive phenylalanine synthesis with overall chemical yield 73% and radioactivity 65.3 nCi. Our suggested synthetic route would be a convenient strategy to label all the novel (mercaptoalkanamido)-3-phenylpropanoic acids. Chromatography column and NMR spectroscopy were used for purifications and identification of desired products, respectively.

Keywords:

β-Lactam antibiotics, β-Lactamase inhibitors , Thiol-carboxylic acid, Carbon-14-labeled, Labeled medicinal compounds

Affiliation:

Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran 16846-13114, Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran 16846-13114, Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran 16846-13114, Department of Analytical Chemistry, University of Valencia, Dr. Moliner 50, 46100, Burjassot, Valencia, Immunology Research Center, Tabriz University of Medical Sciences, Tabriz



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