Chemistry Letters, Vol.46, No.5, 753-755, 2017
Click Reaction Based on the Biosynthesis of Firefly Luciferin
Novel click chemistry was developed based on the biosynthetic process of firefly luciferin, which includes an ideal coupling of a cyanothiazole residue with cysteine. Among various biomimetic couplings of nitriles with cysteine derivatives, the approach using 4-cyanopyridine and cysteine methyl ester provided a very rapid and quantitative conversion to the corresponding thiazole without any metal catalyst at room temperature.