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Synthesis of (2-Mercaptoacetyl)-L-[2-14C]Tryptophan As a Selective Metallo-Β-Lactamase Inhibitor Via [2-14C]Indole Based on Chiral Pool Strategy Publisher Pubmed



Shirvani G1 ; Shockravi A2 ; Amini M3 ; Saemian N1
Authors
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Authors Affiliations
  1. 1. Nuclear Science Research School, Nuclear Science and Technology Research Institute, Tehran, Iran
  2. 2. Faculty of Chemistry, Kharazmi University, Tehran, Iran
  3. 3. Department of Medicinal Chemistry, Faculty of Pharmacy and Drug Design Development Research Center, Tehran University of Medical Sciences, Tehran, Iran

Source: Journal of Labelled Compounds and Radiopharmaceuticals Published:2017


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. Copyright © 2016 John Wiley & Sons, Ltd.
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