Abstract
Herein, a series of aromatic pentafluorosulfanyl (SF5) containing amino acids are reported. A Negishi cross-coupling strategy utilising a catalyst system of Pd(dba)2 and SPhos afforded the aforementioned SF5 amino acids in yields between 32% and 42%. Two dipeptides utilising both the amine and carboxylic functionalities of the synthesised SF5 containing amino acids were prepared, demonstrating their compatibility with common amide/peptide coupling reagents and strategies.
Highlights
The synthesis of novel amino acids is an area of considerable interest as it offers a route to access previously inaccessible natural products and to modulate the properties of peptides [1,2,3]
Negishi cross-coupling has been used to access a wide range of amino acids previously within the literature [26,27]
To begin with a halogenated amino acid precursor 4 was selected as one coupling partner for our Negishi strategy
Summary
The synthesis of novel amino acids is an area of considerable interest as it offers a route to access previously inaccessible natural products and to modulate the properties of peptides [1,2,3]. The ability to include additional functionality (e.g. NMR probes, handles for chemical modification or bioconjugation) within peptide sequences has led to increasing interest in the synthesis of unusual amino acids in areas such as medicinal chemistry [4] and drug discovery [5,6]. Fluorine atoms have been demonstrated to modulate the structure, stability and activity of peptides [7]. The steric bulk and electronics of the SF5 group can modify both the conformation and chemical properties of a compound. This has led to the SF5 group being utilised to develop new pharmaceuticals [9] and agrochemicals [10]
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