A versatile chiral selector for determination of enantiomeric composition of fluorescent and nonfluorescent chiral molecules using steady‐state fluorescence spectroscopy

Abstract

A fluorescent chiral molecular micelle (FCMM), poly (sodium N-undecanoyl-L-phenylalaninate) (poly-L-SUF), was developed as a chiral selector for enantiomeric recognition and determination of enantiomeric composition of four fluorescent and four nonfluorescent chiral molecules by use of steady-state fluorescence spectroscopy. The influence of FCMM concentration, buffer pH and complexation medium on FCMM-analyte host-guest complexation, and the emission spectral properties of the resulting complexes were investigated. The chiral interactions of the analytes,1,1'-binaphthyl-2,2'-diamine, 1-(9-anthryl)-2,2,2-trifluoroethanol, propranolol, naproxen, chloromethyl menthyl ether (CME), citramalic acid, tartaric acid, and limonene (LIM), in the presence of poly-L-SUF were based on diastereomeric complex formation. The figures of merit obtained from the partial-least-squares regression modeling of the calibration samples suggested good prediction ability for the validation of six of the eight chiral analytes. Better host-guest complexation of the more hydrophobic molecules, CME and LIM, were obtained in methanol/water mixtures, resulting in better predictability of the regression models. Prediction ability of the models was evaluated by use of the root-mean-square percent relative error (RMS%RE) and was found to range from 1.77 to 15.80% (buffer), 1.26 to 7.95% (25:75 methanol/water), and 1.21 to 4.28% (75:25 methanol/water).

Chiral fluorescent sensors based on cellulose derivatives bearing terthienyl pendants

“…[5][6][7][8][9][10][11][12] Among them, using fluorescence responses as output signals is considered to be one of the most powerful techniques for chiral discrimination owing to its easy, rapid, sensitive and high-throughput features. [27][28][29] Because the research and development of new pharmaceuticals have been extensively performed all over the world and the kinds of chiral molecules are going on increasing day by day, the development of practical fluorescent sensors that can display good enantioselectivity toward various chiral compounds is strongly required. [21][22][23][24][25][26] However, most of them can only discriminate either central or axial chirality; sensors that can be used for various types of chirality are quite rare.…”

Syntheses and Highly Enantioselective Fluorescent Recognition of α‐Aminocarboxylic Acid Anions Using Chiral Oxacalix[2]arene[2]bisbinaphthes

“…The bisbinaphthyl‐based tweezers fluorescence sensors are found to carry out enantioselective fluorescence probe in the recognition of α‐aminocarboxylic acid derivatives. The compounds acted as a selective flurescence probe in the recognition of α‐aminocarboxylic acid anions with the dramatic change of fluorescence intensity . Following clusters pioneering work, the macrocyclic host molecules crown ethers have attacted increasing interest in recent years.…”

“…[22][23][24][25][26][27][28][29][30] Amongst many of the enantioselective methods under investigation, such as nuclear magnetic resonance (NMR), high-performance liquid chromatography, circular dichroism, especially the use of fluorescence has attracted a sizable interest because it can offer the advantages of real-time analysis, high sensitivity, multiple sensing modes, widely available instrumentation, and remote detection capabilities. [31][32][33][34][35][36][37] Several fluorescent sensors, including those developed within our group, have been reported to show high enantioselectivity in the recognition of mandelic acid and/or tartaric acid or -NH 2 protected by acetyl-group, Boc-group or benzoyl-group amino acid. [38][39][40] However, the enantioselective recognition of native a-aminocarboxylic acid is poor; therefore, the development of enantioselective fluorescent sensors for native a-aminocarboxylic acid has become a major challenge in this area.…”

Ephedrinium‐based protic chiral ionic liquids for enantiomeric recognition

“…52,53 The exact mechanism of chiral recognition is still unclear. Further studies are currently underway to determine the mechanism of chiral recognition by PCILs for analytes of varying chirality.…”