Enantioselective Fluorescent Recognition of β‐Amino Alcohols by Stereoselective Cyclization

Abstract

2,2'-Diformyl-1,1'-binaphthyl is found to exhibit highly enantioselective fluorescence enhancement in the presence of various β-amino alcohols and base. It provides a new method to determine the enantiomeric composition of those substrates and has potential for high throughput analysis. Based on detailed spectroscopic analyses, it is proposed that a stereoselective cyclization of a β-amino alcohol with the probe should occur to form a rigid macrocyclic intermediate, contributing to the greatly enhanced fluorescence.

The Intramolecular Charge Transfer Mechanism by Which Chiral Self-Assembled H8-BINOL Vesicles Enantioselectively Recognize Amino Alcohols

“…In the pharmaceutical industry, the chiral center of the drug molecule can be recognized by the H 8 -BINOL derivative, leading to the preferential formation of one enantiomer over another. This process improves the efficacy and safety of the drug by ensuring that only the desired enantiomer is produced [ 21 , 22 , 23 , 24 ]. In environmental analysis, the H 8 -BINOL derivative is used to identify chiral pollutants in water and soil samples.…”

Enantioselective Recognition of Lysine and Phenylalanine Using an Imidazole Salt-Type Fluorescent Probe Based on H8-BINOL

“…In the past few years, enantioselective fluorescent probes have become a research hotspot and have been widely used for the enantioselective recognition of some amino acids, amino alcohols, and chiral amines [ 1 , 2 , 3 ]; these chiral molecules’ roles are important in organisms and chemical research. In the history of chemical research, many methods have been used to recognize chiral molecules; fluorescence analysis was widely used in enantioselective recognition due to its convenience, high sensitivity, fast and high-throughput analysis, and biological imaging [ 4 ].…”

Fluorous Phase-Enhanced Fluorescent Sensitivity for Enantioselective Recognition of Lysine

“…20−24 Another strategy that could be used to turn on the fluorescence of an imine compound is to introduce a cyclic structure into the imine product to restrict the excited state isomerization and increase the structural rigidity. 25 We propose that when (S,S)-1 is used to interact with most amino acids, there should not be a significant fluorescent response due to the expected formation of poorly emissive imine products from the condensation of the aldehyde groups of this probe with the amine groups of the substrates. However, when lysine is used to react with (S,S)-1, both of the amine groups of lysine could react with the two aldehyde groups of (S,S)-1 to form a macrocyclic compound like 2.…”

“…The two highly fluorinated alkyl groups in ( S,S )- 1 will allow this compound to be soluble in fluorinated solvents and allow fluorescence measurement to be conducted in the fluorous phase. Although various aldehydes have been actively utilized in the development of fluorescent probes for amines, − an imine product formed from the condensation of an aldehyde group with a primary amine is normally nonfluorescent due to the excited state isomerization of the imine double bond. Often, the addition of a metal cation such as Zn 2+ is needed to form chelated coordination with the imine nitrogen and restrict its excited state isomerization to turn on the fluorescence. − Another strategy that could be used to turn on the fluorescence of an imine compound is to introduce a cyclic structure into the imine product to restrict the excited state isomerization and increase the structural rigidity .…”

“…Although various aldehydes have been actively utilized in the development of fluorescent probes for amines, − an imine product formed from the condensation of an aldehyde group with a primary amine is normally nonfluorescent due to the excited state isomerization of the imine double bond. Often, the addition of a metal cation such as Zn 2+ is needed to form chelated coordination with the imine nitrogen and restrict its excited state isomerization to turn on the fluorescence. − Another strategy that could be used to turn on the fluorescence of an imine compound is to introduce a cyclic structure into the imine product to restrict the excited state isomerization and increase the structural rigidity . We propose that when ( S,S )- 1 is used to interact with most amino acids, there should not be a significant fluorescent response due to the expected formation of poorly emissive imine products from the condensation of the aldehyde groups of this probe with the amine groups of the substrates.…”