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 ΔI L/ΔI D) 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.

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Af luorophilic fluorescent probe based on ap erfluoroalkyl-substituted bis(binaphthyl) compound wasd esigned and synthesized.I td isplayed ah ighly enantioselective fluorescencer esponse towards tructurally diverse amino acids in ab iphasic fluorous/aqueous system with enantiomeric fluorescent enhancementr atio (ef; DI D /DI L )v alues up to 45.2 (histidine). It can be used to determinet he enantiomeric compositions of amino acids and also allows the amino acid enantiomerst ob ev isually discriminated. NMR and mass-spectroscopic investigations provided insights into the observedh igh enantioselectivity.T his biphasic fluorescent recognition was used to determine the enantiomeric composition of the crude phenylalanine products generated by an enzyme-catalyzed asymmetrichydrolysis under various reactionc onditions. The fluorous-phase-based fluorescence measurement under the biphasic conditions wasa ble to minimize the interference of other reaction componentsa nd thus has potential in asymmetricreactionscreening.[a] Dr.Y .-Y.Zhu SchoolofC hemistry and EnvironmentalE ngineering Wuhan Institute of Technology, Wuhan4 30205 (P.R.C hina)[b] Dr.