Enantioselectivity in Developmental Toxicity of rac‐metalaxyl and R‐metalaxyl in Zebrafish (Danio rerio) Embryo

Enantioselectivity of chiral pesticides in environmental safety has attracted more and more attention. In this study, we evaluated the enantioselective toxicity of rac‐metalaxyl and R‐metalaxyl to zebrafish (Danio rerio) embryos through various malformations including pericardial edema, yolk sac edema, crooked body, and short tails. The results showed that there were significant differences in toxicity to zebrafish embryos caused by rac‐metalaxyl and R‐metalaxyl, and the LC₅₀s at 96 h are 416.41 (353.91, 499.29) mg · L^‐1 and 320.650 (279.80, 363.46) mg · L^‐1, respectively. In order to explore the possible mechanism of the development defects, the genes involved in the hypothalamic–pituitary–gonadal axis (vtg1, vtg2, cyp17, cyp19a, cyp19b) and hypothalamic–pituitary–thyroid axis (dio1, dio2, nis, tg, tpo) were quantified by quantitative real‐time polymerase chain reaction (qRT‐PCR). The results revealed that there were no significant differences in the expression of vtg1, vtg2, cyp17, cyp19a, and cyp19b after exposure to rac‐metalaxyl. However, the expression of vtg1, cyp19a, and cyp19b decreased significantly after exposure to R‐metalaxyl. And likewise, rac‐metalaxyl only caused the upregulation of dio2, while R‐metalaxyl suppressed the expression of dio1 and tpo and induced the expression of dio2 and nis. The change of gene expression may cause the enantioselectivity in developmental toxicity in zebrafish embryo. The data provided here will be helpful for us to comprehensively understand the potential ecological risks of the currently used chiral fungicides. Chirality 28:489–494, 2016. © 2016 Wiley Periodicals, Inc.     

A New Biosensor for Chiral Recognition Using Goat and Rabbit Serum Albumin Self‐Assembled Quartz Crystal Microbalance

Quartz crystal microbalance (QCM) biosensor was used for the chiral recognition of five pairs of enantiomers by using goat serum albumin (GSA) and rabbit serum albumin (RbSA) as chiral selectors. Serum albumin (SA) was immobilized on the QCM through the self‐assembled monolayer technique, and the surface concentration of GSA and RbSA were 8.8 × 10^?12 mol cm^?2 and 1.2 × 10^?11 mol cm^?2, respectively. The QCM biosensors showed excellent sensitivity and selectivity. Meanwhile, the chiral recognition of SA sensors was quite species dependent. There were differences between GSA and RbSA sensors in the ability and the preference of chiral recognition. To R,S‐1,2,3,4‐tetrahydro‐1‐naphthylamine (R,S‐1‐TNA), R,S‐1‐(4‐methoxyphenyl)ethylamine (R,S‐4‐MPEA), and R,S‐1‐(3‐methoxyphenyl)ethylamine (R,S‐3‐MPEA), the preference of the stereoselective SA‐drug binding of the two kinds of SA sensors were consistent. However, to R,S‐2‐octanol (R, S‐2‐OT) and R,S‐methyl lactate (R,S‐MEL), the two kinds of SA sensors had opposite chiral recognition preference. Moreover, the interactions of SA and the five pairs of enantiomers have been further investigated through ultraviolet (UV) and fluorescent (FL) spectra. The UV/FL results were in accordance with the consequence of QCM. Chirality 24:804–809, 2012. © 2012 Wiley Periodicals, Inc.     

(S)‐(−)‐(2‐MeBu)N(Pr)2MeI Salt as Template in the Enantioselective Synthesis of the Enantiopure Two‐dimensional (S)‐(−)‐(2‐MeBu)N(Pr)2Me[ΛMnΔCr(C2O4)3] Ferromagnet

We describe herein the synthesis of (rac)‐ or enantiopure (S)‐(?)‐(2‐MeBu)N(Pr)₂MeI ammonium salts. These racemic and enantiopure ammonium salts were used as cationic templates to obtain new two‐dimensional (2D) ferromagnets [(rac)‐(2‐MeBu)N(Pr)₂Me][MnCr(C₂O₄)₃] and [(S)‐(?)‐(2‐MeBu)N(Pr)₂Me][ΔMnΛ nCr(C₂O₄)₃]. The absolute configuration of the hexacoordinated Cr(III) metallic ion in the enantiopure 2D network was determined by a circular dichroism measurement. The structure of [(2‐MeBu)N(Pr)₂Me][MnCr(C₂O₄)₃], established by single crystal X‐ray diffraction, belongs to the chiral P6₃ space group. According to direct current (dc) magnetic measurements, these compounds are ferrromagnets with a temperature Tc = 6°K. Chirality 25:444–448, 2013. © 2013 Wiley Periodicals, Inc.     

Solution properties of the nickel(II,III) and copper(II,III) complexes of trans-dioxocyclam (trans-dioxocyclam=5,12-dioxo-1,4,8,11-tetraazacyclotetradecane) and the X-ray crystal structure of the N-rac-isomer of the nickel(II) complex

The crystal and molecular structures of the N-rac-isomer of the nickel(II) complex of 14-membered amide-containing macrocycle [NiL¹] · 4H₂O (H₂L¹=5,12-dioxo-1,4,8,11-tetraazacyclotetradecane) have been determined. Two deprotonated amide and two amine donors co-ordinate to the nickel(II) in nearly square planar manner with Ni-N_amine bonds longer than Ni-N_amide ones (1.930 vs. 1.898 Å). Water molecules do not co-ordinate and form hydrogen bond bridges between macrocyclic units in the crystal lattice. The analysis of ¹H NMR data confirmed that the solid-state conformation of the macrocycle in N-rac[NiL¹] is retained in aqueous solution though equilibrated with some amount of N-meso isomer. The comparison of the spectroscopic characteristics of the M(II) and M(III) complexes and the redox potentials of M(III/II) couples (M=Ni and Cu) for ML¹ with those for ML²(H₂L²=5,7-dioxo-1,4,8,11-tetraazacyclotetradecane) revealed a rather small influence of the trans- vs. cis-arrangement of amide donors in co-ordination spheres of the metal ions.     

DNA Binding,Antioxidant Activity,and DNA Damage Protection of Chiral Macrocyclic Mn(III) Salen Complexes

We are reporting the synthesis, characterization, and calf thymus DNA binding studies of novel chiral macrocyclic Mn(III) salen complexes S‐1 , R‐1 , S‐2 , and R‐2 . These chiral complexes showed ability to bind with DNA, where complex S‐1 exhibits the highest DNA binding constant 1.20 × 10⁶ M^?1. All the compounds were screened for superoxide and hydroxyl radical scavenging activities; among them, complex S‐1 exhibited significant activity with IC₅₀ 1.36 and 2.37 μM, respectively. Further, comet assay was used to evaluate the DNA damage protection in white blood cells against the reactive oxygen species wherein complex S‐1 was found effective in protecting the hydroxyl radicals mediated plasmid and white blood cells DNA damage. Chirality 24:1063–1073, 2012.© 2012 Wiley Periodicals, Inc.     

Self‐assembly and chiral recognition of quartz crystal microbalance chiral sensor

A novel chiral sensor based on the self‐assembled monolayer of (6^A‐ω‐mercaptoethylureado‐6^A‐deoxy)heptakis(2,3‐di‐o‐phenylcarbamoyl)‐6^B, 6^C, 6^D, 6^E, 6^F, 6^G‐ hexa‐o‐phenylcarbamoyl‐β‐cyclodextrin (Ph‐β‐CD‐SH) on a quartz crystal transducer for chiral recognition was set up. (R,S)‐(±)‐(3‐Methoxyphenyl)ethylamine were recognized by this QCM chiral sensor with a QCM chiral discrimination factor of 1.33. Furthermore, UV spectroscopy was used to investigate the mechanism of host‐guest interactions between (6^A‐azido‐6^A‐deoxy)heptakis(2,3‐di‐o‐phenylcarbamoyl)‐6^B, 6^C, 6^D, 6^E, 6^F, 6^G‐hexa‐o‐phenylcarbamoyl‐β‐cyclodextrin (Ph‐β‐CD) and (R,S)‐(±)‐(3‐methoxyphenyl) ethylamine. The UV discrimination factor was determined to be 0.066. Chirality, 2010. © 2009 Wiley‐Liss, Inc.     

Enantioselective Photolysis and Quantitative Chiral Analysis of Tryptophan Complexed With Alkali‐Metalized L‐Serine in the Gas Phase

The enantioselective photolysis of a cold gas‐phase noncovalent complex of tryptophan with alkali‐metalized L‐serine, M⁺(L‐Ser)(Trp) (M = Na and Li), was examined using a tandem mass spectrometer containing a variable‐temperature ion trap. CO₂ loss from Trp in the clusters was enantiomerically selective in ultraviolet excitation with linearly polarized light. M⁺(L‐Ser) promoted the enantioselective photolysis of Trp as a chiral auxiliary. The enantioselective photolysis of the D‐enantiomer was applied to a quantitative chiral analysis, in which the optical purity of tryptophan could be determined by measuring the relative abundance ratio R of the enantioselective CO₂ loss to the chiral‐independent evaporation of L‐Ser in a single photodissociation mass spectrum of M⁺(L‐Ser)(Trp). Chirality 27:349–352, 2015. © 2015 Wiley Periodicals, Inc.     

Tetrathiafulvalene‐[2.2]paracyclophanes: Synthesis,crystal structures,and chiroptical properties

Two racemic tetrathiafulvalene‐[2.2]paracyclophane electron donors EDT‐TTF‐[2.2]paracyclophane 1 and (COOMe)₂‐TTF‐[2.2]paracyclophane 2 have been synthesized via the phosphite mediated cross coupling strategy. Chiral HPLC allowed the optical resolution of the (R_P) and (S_P) enantiomers for both compounds. Solid‐state structures of (R_P)‐ 1 and (rac)‐ 2 have been determined by single crystal X‐ray analysis. Intermolecular π‐π and S???S interactions are disclosed in the packing. Single crystal X‐ray analysis of (R_P)‐ 1 combined with experimental and theoretical circular dichroism spectra allowed the assignment of the absolute configuration of the enantiomers of 1 and 2 .     

Crystallographic studies for the chiral recognition of the novel chiral stationary phase derived from (+)‐(R)‐18‐crown‐6 tetracarboxylic acid

Chiral discrimination observed in high‐performance liquid chromatography (HPLC) with the novel chiral stationary phase (CSP‐18C6I) derived from (+)‐(R)‐18‐crown‐6 tetracarboxylic acid [(+)‐18C6H₄] was investigated by X‐ray crystallographic analysis of the complex composed of the R‐enantiomer of 1‐(1‐naphthyl)ethylamine (1‐NEA) and (+)‐18C6H₄. Mixtures of 1‐NEA (the R‐ or S‐enantiomer) and (+)‐18C6H₄ were dissolved in methanol‐water (1:1) solution and allowed to stand for crystallization. The R‐enantiomer crystallized with (+)‐18C6H₄ as a co‐crystal, although the S‐enantiomer did not. This result was in good agreement with the enantiomer elution order of 1‐NEA in CSP‐18C6I. The apparent binding constants (K_a) of the enantiomers to the (+)‐18C6H₄ obtained from ¹H‐NMR experiments also supported the above‐mentioned result. The X‐ray crystal structure of the 1:1 complex of the R‐enantiomer and (+)‐18C6H₄ indicated the four sets of hydrogen bond association between the naphthylethylammonium cation and oxygen of polyether ring or carbonyl group of (+)‐18C6H₄. Chirality 11:173–178, 1999. © 1999 Wiley‐Liss, Inc.     

Synthetic Method for 2,2'‐Disubstituted Fluorinated Binaphthyl Derivatives and Application as Chiral Source in Design of Chiral Mono‐Phosphoric Acid Catalyst

A practical synthetic method for 2,2'‐disubstituted fluorinated binaphthyl derivatives was achieved using magnesium bis(2,2,6,6‐tetramethylpiperamide) [Mg(TMP)₂], prepared from LiTMP (2 equiv) and MgBr₂ (1 equiv), which allows for access to a variety of fluorinated binaphthyl compounds. The utility of the fluorinated binaphthyl backbone was evaluated in F₁₀BINOL derived chiral mono‐phosphoric acid (R)‐ 19 as the chiral Brønsted acid catalyst. The catalyst (R)‐ 19 performs exceptionally well in the catalytic enantioselective imino‐ene reaction, demonstrating the potential of a fluorinated binaphthyl framework. Chirality 27:464–475, 2015. © 2015 Wiley Periodicals, Inc.     

Synthesis of enantiopure planar chiral bis‐(para)‐pseudo‐meta‐type [2.2]paracyclophanes

A new type of planar chiral (R_p)‐ and (S_p)‐4,7,12,15‐tetrasubstituted [2.2]paracyclophanes was prepared from racemic 4,7,12,15‐tetrabromo[2.2]paracyclophane as the starting substrate. Regioselective lithiation and transformations afforded racemic bis‐(para)‐pseudo‐meta‐type [2.2]paracyclophane (4,15‐dibromo‐7,12‐dihydroxy[2.2]paracyclophane). Its optical resolution was performed by the diastereomer method using a chiral camphanoyl group as the chiral auxiliary. The diastereoisomers were readily isolated by simple silica gel column chromatography, and the successive hydrolysis afforded (R_p)‐ and (S_p)‐bis‐(para)‐pseudo‐meta‐type [2.2]paracyclophanes ((R_p)‐ and (S_p)‐4,15‐dibromo‐7,12‐dihydroxy[2.2]paracyclophanes). They can be used as pseudo‐meta‐substituted chiral building blocks.     

Enantiomeric Specificity of Biologically Significant Cu(II) and Zn(II) Chromone Complexes Towards DNA

Novel chiral Schiff base ligands (R)/(S)‐2‐amino‐3‐(((1‐hydroxypropan‐2‐yl)imino)methyl)‐4H‐chromen‐4‐one (L₁ and L₂) derived from 2‐amino‐3‐formylchromone and (R/S)‐2‐amino‐1‐propanol and their Cu(II)/Zn(II) complexes ( R1 , S1 , R2 , and S2 ) were synthesized. The complexes were characterized by elemental analysis, infrared (IR), hydrogen (¹H) and carbon (¹³C) nuclear magnetic resonance (NMR), electrospray ionization‐mass spectra (ESI‐MS), and molar conductance measurements. The DNA binding studies of the complexes with calf thymus were carried out by employing different biophysical methods and molecular docking studies that revealed that complexes R1 and S1 prefers the guanine–cytosine‐rich region, whereas R2 and S2 prefers the adenine–thymine residues in the major groove of DNA. The relative trend in K_b values followed the order R1 S1 R2 S2 . This observation together with the findings of circular dichroic and fluorescence studies revealed maximal potential of (R)‐enantiomeric form of complexes to bind DNA. Furthermore, the absorption studies with mononucleotides were also monitored to examine the base‐specific interactions of the complexes that revealed a higher propensity of Cu(II) complexes for guanosine‐5′‐monophosphate disodium salt, whereas Zn(II) complexes preferentially bind to thymidine‐5′‐monophosphate disodium salt. The cleavage activity of R1 and R2 with pBR322 plasmid DNA was examined by gel electrophoresis that revealed that they are good DNA cleavage agents; nevertheless, R1 proved to show better DNA cleavage ability. Topoisomerase II inhibitory activity of complex R1 revealed that the complex inhibits topoisomerase II catalytic activity at a very low concentration (25 μM). Furthermore, in vitro antitumor activity of complexes R1 and S1 were screened against human carcinoma cell lines of different histological origin. Chirality 24:977–986, 2012. © 2012 Wiley Periodicals, Inc.     

Circularly polarized luminescence of Sm (III) and Eu (III) complexes with chiral ligand (R/S)‐BINAPO

Luminescent lanthanide (III) ions have been exploited for circularly polarized luminescence (CPL) for decades. However, very few of these studies have involved chiral samarium (III) complexes. Complexes are prepared by mixing axial chiral ligands (R/S))‐2,2’‐bis(diphenylphosphoryl)‐1,1′‐binaphthyl (BINAPO) with europium and samarium Tris (trifluoromethane sulfonate) (Eu (OTf)₃ and Sm (OTf)₃). Luminescence‐based titration shows that the complex formed is Ln((R/S)‐BINAPO)₂(OTf)₃, where Ln = Eu or Sm. The CPL spectra are reported for Eu((R/S)‐BINAPO)₂(OTf)₃ and Sm((R/S)‐BINAPO)₂(OTf)₃. The sign of the dissymmetry factors, g_em, was dependent upon the chirality of the BINAPO ligand, and the magnitudes were relatively large. Of all of the complexes in this study, Sm((S)‐BINAPO)₂(OTf)₃ has the largest g_em = 0.272, which is one of the largest recorded for a chiral Sm³⁺ complex. A theoretical three‐dimensional structural model of the complex that is consistent with the experimental observations is developed and refined. This report also shows that (R/S)‐BINAPO are the only reported ligands where g_em (Sm³⁺) > g_em (Eu³⁺).     

The determination of enantiomer composition of 1‐((3‐chlorophenyl)‐(phenyl)methyl) amine and 1‐((3‐chlorophenyl)(phenyl)‐methyl) urea (Galodif) by NMR spectroscopy,chiral HPLC,and polarimetry

For the first time, a method for enantiomer resolution of the anticonvulsant Galodif (1‐((3‐chlorophenyl)(phenyl)methyl) urea) by chiral HPLC was developed, whereas the enantiomeric composition of 1‐((3‐chlorophenyl)(phenyl)methyl) amine—precursor in Galodif synthesis—cannot be resolved by this method. However, starting 1‐((3‐chlorophenyl)(phenyl)methyl) amine quantitatively forms diastereomeric N‐((3‐chlorophenyl)(phenyl)methyl)‐1‐camphorsulfonamides in reaction with chiral (1R)‐(+)‐ or (1S)‐(?)‐camphor‐10‐sulfonyl chlorides. The diastereomeric ratio of obtained camphorsulfonamides can be easily determined by NMR ¹H and ¹³C spectroscopy. The DFT calculations of specific rotation of Galodif enantiomers showed good agreement with experimental data. The absolute configuration of enantiomers was proposed for the first time.     

Enantioselective Surface Plasmon Resonance Sensor Based on C60 Fullerene‐Glutathione Self‐Assembled Monolayer (SAM)

A novel enantioselective surface plasmon resonance (SPR) sensor based on a self‐assembled monolayer of C₆₀ fullerene as the chiral selector is proposed. A binding assay, apparent affinity constant, and apparent dissociation binding constant were used to analyze and study the enantioselectivity of C₆₀ fullerene‐glutathione film for L‐histidine, which was chosen as the model analyte. The apparent affinity constant for the complex formed by L‐histidine with C₆₀ fullerene‐glutathione film was 5.2 x 10⁹ M^‐1. The proposed SPR sensor can be used for the assay of L‐histidine in the 10^‐10 – 10^‐7 mol/L concentration range. Chirality 26:129–131, 2014. © 2014 Wiley Periodicals, Inc.     

A New Chiral Residue Analysis Method for Triazole Fungicides in Water Using Dispersive Liquid‐Liquid Microextraction (DLLME)

A rapid, simple, reliable, and environment‐friendly method for the residue analysis of the enantiomers of four chiral fungicides including hexaconazole, triadimefon, tebuconazole, and penconazole in water samples was developed by dispersive liquid–liquid microextraction (DLLME) pretreatment followed by chiral high‐performance liquid chromatography (HPLC)‐DAD detection. The enantiomers were separated on a Chiralpak IC column by HPLC applying n‐hexane or petroleum ether as mobile phase and ethanol or isopropanol as modifier. The influences of mobile phase composition and temperature on the resolution were investigated and most of the enantiomers could be completely separated in 20 min under optimized conditions. The thermodynamic parameters indicated that the separation was enthalpy‐driven. The elution orders were detected by both circular dichroism detector (CD) and optical rotatory dispersion detector (ORD). Parameters affecting the DLLME performance for pretreatment of the chiral fungicides residue in water samples, such as the extraction and dispersive solvents and their volume, were studied and optimized. Under the optimum microextraction condition the enrichment factors were over 121 and the linearities were 30–1500 µg L^?1 with the correlation coefficients (R²) over 0.9988 and the recoveries were between 88.7% and 103.7% at the spiking levels of 0.5, 0.25, and 0.05 mg L^?1(for each enantiomer) with relative standard deviations varying from 1.38% to 6.70% (n = 6) The limits of detection (LODs) ranged from 8.5 to 29.0 µg L^?1(S/N = 3). Chirality 25:567‐574, 2013. © 2013 Wiley Periodicals, Inc.     

Chiral Resolution and Absolute Configuration of the Enantiomers of the Psychoactive “Designer Drug” 3,4‐Methylenedioxypyrovalerone

Illicit rac‐MDPV (3,4‐methylenedioxypyrovalerone), manufactured in clandestine labs, has become widely abused for its cocaine‐like stimulant properties. It has recently been found as one of the toxic materials in the so‐called “bath salts,” producing, among other effects, psychosis and tachycardia in humans when introduced by any of the several routes of administration (e.g., intravenous, oral, etc.). The considerable toxicity of this “designer drug” probably resides in one of the enantiomers of the racemate. In order to obtain a sufficient amount of the enantiomers of rac‐MDPV to determine their activity, we improved the known synthesis of rac‐MDPV and found chemical resolving agents, (+)‐ and (–)‐2’‐bromotetranilic acid, that gave the MDPV enantiomers in >96% enantiomeric excess as determined by ¹H nuclear magnetic resonance and chiral high‐performance liquid chromatography. The absolute stereochemistry of these enantiomers was determined by single‐crystal X‐ray diffraction studies. Chirality 27:287‐293, 2015. Published 2015. This article is a U.S. Government work and is in the public domain in the USA.     

Enantioselective recognition of carboxylic acids by novel fluorescent triazine‐based thiazoles

Hydrogen bonding and π‐π interactions take special part in the enantioselectivity task. In this regard, because of having both hydrogen acceptor and hydrogen donor groups, melamine derivatives become more of an issue for enantioselectivity. In the light of such information, triazine‐based chiral, fluorescence active novel thiazole derivatives L1 and L2 were designed and synthesized from (S)‐(?)‐2‐amino‐1‐butanol and (1S,2R)‐(+)‐2‐amino‐1,2‐diphenylethanol. The structural establishment of these compounds was made by spectroscopic methods such as FTIR, ¹H, and ¹³C NMR. While the solution of these compounds in DMSO did not show any fluorescence emission, it was observed that the emission increased 44‐fold for L1 and 55‐fold for L2 in 95% water, similar to the aggregation‐induced emission (AIE) characterized compounds. In this regard, enantioselective capabilities of these compounds against carboxylic acids were tested, and in experiments carried out at a ratio of 40/60 DMSO/H₂O, it was determined that R‐2ClMA increased the fluorescence emission of L1 chiral receptor by 2.59 times compared to S‐isomer.     

Comparative HPLC Enantioseparation of Thirty‐Six Aromatic Compounds on Four Columns of the Lux® Series: Impact of Substituents,Shapes and Electronic Properties

With the aim to define a combined computational/chromatographic empirical approach useful for the high‐performance liquid chromatography (HPLC) method development of new chiral compounds, 36 racemic aromatic compounds with different chemical structures were used as test probes on four polysaccharide‐based chiral stationary phases (CSPs) of the Lux series, namely Lux Cellulose‐1, Lux Cellulose‐2, Lux Cellulose‐4, and Lux Amylose‐2, using classical n‐hexane/2‐propanol mixtures as mobile phase. Electrostatic potential surfaces (EPSs) determined using Density Functional Theory (DFT) calculations were used to derive size, shape, and electronic properties of each analyte. Then a comparative HPLC screening was carried out in order to evaluate the impact of substituents, shapes, and electronic properties of the analytes on the chromatographic behavior as the column changes. The four CSPs showed good complementary recognition ability. The elution sequence was determined in 30 cases out of 36. The success rate to afford baseline separations (R_s ≥ 1.5) was estimated: 29 compounds out of 36 showed baseline enantioseparation on at least one of the four selected CSPs. The combined computational‐chromatographic screening furnished useful collective structure‐chromatographic behavior relationships and a map of the chiral discrimination abilities of the considered CSPs towards the analytes. On this basis, the chromatographic behavior of new analytes on a set of polysaccharide‐based CSPs can be mapped through the qualitative correlation of chromatographic parameters (k, α, R_s) to computed molecular properties of the analytes. Chirality 25:709–718, 2013. © 2013 Wiley Periodicals, Inc.     

Solid‐phase extraction with metal–organic frameworks for the analysis of chiral compounds

Metal–organic frameworks (MOFs) are excellent porous materials with nanoscale cavities and high surface areas, which make them promising as novel adsorbents in solid‐phase extraction (SPE). In this article we report a new application of the chiral MOF [Zn₂(D‐Cam)₂(4,4′‐bpy)]_n in SPE used for the measurement of the enantiomeric excess (ee) of (±)‐1,1′‐bi‐2‐naphthol. Several important experimental parameters that may influence the extraction efficiency were investigated and optimized. Under the optimum conditions, a good linearity (R² > 0.999) was found between the ee value and the reciprocal of the peak areas. When compared with the actual ee measured using chiral HPLC, the SPE‐based assay also showed good accuracy and precision. The results showed that SPE based on chiral MOFs as adsorbents is a simple and effective method for the determination of the ee values of chiral compounds.