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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

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.