Synthesis of (2-mercaptoacetyl)-L-[2-¹⁴C]tryptophan as a selective metallo-β-lactamase inhibitor via [2-¹⁴C]indole based on chiral pool strategy

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• 作者：Gholamhossein Shirvani ; Abbas Shockravi ; Mohsen Amini and Nader Saemian
• 刊名：Journal of Labelled Compounds and Radiopharmaceuticals
• 出版年：2017
• 出版时间：February 2017
• 年：2017
• 卷：60
• 期：2
• 页码：130-134
• 全文大小：373K
• ISSN：1099-1344

文摘

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.