Synthesis of a new metal chelating amino acid: Terpyridyl-alanine

Add time:08/28/2019    Source:sciencedirect.com

In past years, terpyridine-containing substances have been found useful in polynucleotide chemistry and enzymatic engineering applications. Therefore, the construction of a noncanonical amino acid with a terpyridine side chain may offer promising features for in vitro and in vivo applications, such as the direct bio-expression of proteins with these substances as building blocks. The first step towards these goals is to establish a synthetic protocol for a terpyridine analog bearing an amino acid moiety. Here, we demonstrate the synthesis of terpyridyl-alanine for the first time in five steps and an overall yield of 50%. A metal complex with Fe(II) ions was prepared by crystallization of a protected terpyridyl-alanine derivative and analyzed by X-ray crystallography. Complex formation in aqueous solution was studied by 1H-NMR, UV/Vis and fluorescence spectroscopy. The comparison of five transition metal ions revealed a metal dependent shift in the UV-absorption and a strong fluorescence in the presence of Zn(II) ions.

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