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Synthesis of (2‐mercaptoacetyl)‐L‐[2‐ 14 C]tryptophan as a selective metallo‐β‐lactamase inhibitor via [2‐ 14 C]indole based on chiral pool strategy
Author(s) -
Shirvani Gholamhossein,
Shockravi Abbas,
Amini Mohsen,
Saemian Nader
Publication year - 2017
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3485
Subject(s) - chemistry , indole test , tryptophan , stereochemistry , ring (chemistry) , yield (engineering) , beta lactam , enzyme , amino acid , combinatorial chemistry , organic chemistry , antibiotics , biochemistry , materials science , metallurgy
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‐ 14 C]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 [ 14 C]carbonate as a starting material.