title: Synthesis of (2-mercaptoacetyl)-L-[2-14C]tryptophan as a selective metallo-β-lactamase inhibitor via [2-14C]indole based on chiral pool strategy.
abstract: Metallo-beta-lactamase enzymes make bacteria resistant to a broad range of commonly used beta-lactam antibiotics. Several thiol derivatives of L-amino acids have been shown their inhibitory effects against the metallo-β-lactamase IMP-1. In this study, (2-mercaptoacetyl)-L-tryptophan as a new inhibitor of metallo-β-lactamases labeled with carbon-14 in the 2-position of the indole ring was prepared from [2-14C]indole as a key synthetic intermediate based on chiral pool strategy. The overall synthesis was performed in 10 steps with the overall radiochemical yield 3.6% on the basis of the barium [14C]carbonate as a starting material.
authors.affiliation: Nuclear Science Research School, Nuclear Science and Technology Research Institute, Tehran, Iran.
authors.forename: Gholamhossein
authors.initials: G
authors.lastname: Shirvani
authors.affiliation: Faculty of Chemistry, Kharazmi University, Tehran, Iran.
authors.forename: Abbas
authors.initials: A
authors.lastname: Shockravi
authors.affiliation: Department of Medicinal Chemistry, Faculty of Pharmacy and Drug Design Development Research Center, Tehran University of Medical Sciences, Tehran, Iran.
authors.forename: Mohsen
authors.initials: M
authors.lastname: Amini
authors.affiliation: Nuclear Science Research School, Nuclear Science and Technology Research Institute, Tehran, Iran.
authors.forename: Nader
authors.initials: N
authors.lastname: Saemian
mesh_terms: D001464:Barium / Q000737:chemistry; D002250:Carbon Radioisotopes / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry; D007211:Indoles / Q000737:chemistry; D019275:Radiopharmaceuticals / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D065093:beta-Lactamase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D001618:beta-Lactamases / Q000378:metabolism
chemical_list: C000625391:(2-mercaptoacetyl)tryptophan; D002250:Carbon Radioisotopes; D002254:Carbonates; D007211:Indoles; D019275:Radiopharmaceuticals; D013438:Sulfhydryl Compounds; D065093:beta-Lactamase Inhibitors; D001464:Barium; C006685:barium carbonate; D014364:Tryptophan; C409201:beta-lactamase IMP-1; D001618:beta-Lactamases
keywords: amino acid; antibiotics; carbon-14; indole; metallo-β-lactamase's inhibitors