Beilstein J. Org. Chem.2017,13, 2869–2882, doi:10.3762/bjoc.13.279
][40]. 2-Aminobutanoic acid (Abu) and its fluorinated analogues 2-amino-4,4-difluorobutanoic acid (DfeGly) and 2-amino-4,4,4-trifluorobutanoic acid (TfeGly) were individually incorporated at either the P2, the P1’ or the P2’ position [41] to give nine different analogues of FA. In prior studies, we
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Graphical Abstract
Figure 1:
(a) Structures of isoleucine (1), leucine (2), and their fluorinated analogues 5,5,5-trifluoroisole...
Beilstein J. Org. Chem.2010,6, No. 40, doi:10.3762/bjoc.6.40
protein environment and to enable the design of fluorinated proteins with arbitrary desired properties.
Keywords: chemical aminoacylation; DfeGly; fluorinated amino acids; site-specific protein mutagenesis; TfeGly; TfmAla; Introduction
Over the past two decades, the interest in engineering proteins
)-ethylglycine (Abu) and two of its fluorinated analogues, (S)-2-amino-4,4-difluorobutanoic acid (DfeGly) [23] and (S)-2-amino-4,4,4-trifluorobutanoic acid (TfeGly) [24], were synthesized in the appropriate protected activated form and used to chemically aminoacylate tRNAPheCUA by means of the hybrid
acids were activated as their corresponding cyanomethyl esters (Scheme 1).
The N-(4-pentenoyl) protection of Abu and its fluorinated analogues DfeGly and TfeGly, and the preparation of their cyanomethyl esters were performed as described by Hecht and co-workers [7][9]. In the first step, the amino acid
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Graphical Abstract
Figure 1:
General strategy of using a chemically aminoacylated suppressor tRNA and an in vitro translation sy...