Quantum mechanics

Catalysis

Valine

Enantioselective synthesis

Amino acid

Leucine

Methionine

Enantiomer

Biochemistry

Substrate (aquarium)

Geology

Alanine

Stereochemistry

Oceanography

Combinatorial chemistry

Physics

Organic chemistry

Fluorescence

Chemistry

Phenylalanine

Aromatic amino acids

Journal of the American Chemical Society

A novel fluorescent probe based on a bisbinaphthyl structure has been designed and synthesized. This compound in combination with Zn(II) has exhibited highly enantioselective fluorescence enhancement with 13 common free amino acids. For example, its enantiomeric fluorescent enhancement ratios (ef or ΔIL/ΔID) in the presence of the following amino acids are extremely high: 177 for valine, 199 for methionine, 186 for phenylalanine, 118 for leucine, and 89 for alanine. The observed high enantioselectivity and the extent of the substrate scope are unprecedented in the fluorescent recognition of free amino acids. This fluorescent probe can be applied to determine the enantiomeric composition of the structurally diverse chiral amino acids. NMR and mass spectroscopic investigations have provided clues to elucidate the observed high enantioselectivity.

Free Amino Acid Recognition: A Bisbinaphthyl-Based Fluorescent Probe with High Enantioselectivity