Highly chemoselective and enantioselective recognition of serine by a fluorescent probe

A diarylacetylene-containing 1,1'-bi-2-naphthol derivative (R)-2 was designed and synthesized. This compound in combination with Zn2+ represents the first chemoselective as well as enantioselective fluorescent probe for the biologically important amino acid serine. It was found that L-serine can greatly enhance the fluorescence of the probe at lambda = 471 nm but o-serine and 17 other common amino acids cannot. An enantioselective fluorescence enhancement ratio [ef = (I-L - I-0)/(I-D - I-0) = Delta I-L/Delta I-D] of 15 was observed for the response of (R)-2 + Zn2+ toward serine. (C) 2021 Elsevier Ltd. All rights reserved.