A chiral phosphorous derivatizing agent prepared from PCl3 and (S)-BINOL was described. It is used to determine the enantiomeric excess of chiral alcohols and amines by 31P NMR.
Simulated enantiomeric excess of glutamic acid was determined by a lab-made sixteen-channel capillary array electrophoresis with confocal fluorescent rotary scanner. The experimental results indicated that the capilla...Simulated enantiomeric excess of glutamic acid was determined by a lab-made sixteen-channel capillary array electrophoresis with confocal fluorescent rotary scanner. The experimental results indicated that the capillary array electrophoresis method can accurately determine the enanfiomefic excess of glutamic acid and can be used for high-throughput screening system for combinatorial asymmetric catalysis.展开更多
Enantiomer of n-pyrrolidinyl phenylpropanol was studied by capillary electrophoresis using b-cyclodextrin polymer as chiral selector. We determined the enantiomeric excess value of n-pyrrolidinyl phenylpropanol with R...Enantiomer of n-pyrrolidinyl phenylpropanol was studied by capillary electrophoresis using b-cyclodextrin polymer as chiral selector. We determined the enantiomeric excess value of n-pyrrolidinyl phenylpropanol with RSD 0.48%.展开更多
Using four β-cyclodextrin derivatives, 2,6-di-O-benzyl-3-O-heptanonyl-β-CD, 2,6-di- O-benzyl-3-O-octanonyl-β-CD, 2,3-di-O-benzyl-6-O-heptanonyl-β-CD, and 2,3-di-O-benzyl -6-O- octanonyl-β-CD, as chiral stationary...Using four β-cyclodextrin derivatives, 2,6-di-O-benzyl-3-O-heptanonyl-β-CD, 2,6-di- O-benzyl-3-O-octanonyl-β-CD, 2,3-di-O-benzyl-6-O-heptanonyl-β-CD, and 2,3-di-O-benzyl -6-O- octanonyl-β-CD, as chiral stationary phases of capillary gas chromatography （CGC）, the enantiomers of Sharpless epoxides were well separated. The enantiomer excess values （e.e.%） of some chiral Sharpless epoxides were also determined successfully using these CDs.展开更多
Four types of chiral thiazolidine derivatives were synthesized conveniently from natural L-cysteine and showed good enantioselectivity in up to 90% ee in the addition of diethylzine to benzaldehyde. Their enantioselec...Four types of chiral thiazolidine derivatives were synthesized conveniently from natural L-cysteine and showed good enantioselectivity in up to 90% ee in the addition of diethylzine to benzaldehyde. Their enantioselectivity was affected by the bulkiness of R and the thiazolidine ring systems in their molecules.展开更多
Chiral tetraphenylethylene(TPE) dicycle tetraaldehyde and TPE dicycle tetraacids bearing optically pure groups on the cycles were designed and synthesized. Due to the propeller-like conformation immobilization of TPE ...Chiral tetraphenylethylene(TPE) dicycle tetraaldehyde and TPE dicycle tetraacids bearing optically pure groups on the cycles were designed and synthesized. Due to the propeller-like conformation immobilization of TPE unit, this new class of TPE dicycle was resolved into M-and P-enantiomers, which could emit strong circular polarized luminescence(CPL). Interestingly,these TPE helicates displayed exceptional ability of molecule recognition. While the TPE dicycle tetraaldehyde could detect the microscale water in anhydrous tetrahydrofuran, the chiral TPE dicycle tetraacid could display different fluorescent color after interacting with two enantiomers of a wide variety of chiral amines including monoamines, diamines, and aminols, which could be applied to chiral recognition of these chiral amines. Furthermore, the emission wavelength of TPE dicycle tetraacid was found to change linearly with the enantiomer purity of chiral amine from enantiomer excess(ee) percent-100% to +100%, for the first time showing the potential for quantitative chiral analysis of chiral amines based on emission wavelength change. The emission wavelength was affected less by environmental factors than fluorescence intensity, which would enable the chiral analysis based on wavelength change with higher accuracy and repeatability.展开更多
A novel BINOL-based fluorescence probe(S)-6 featuring a sodium sulfonate fragment at the 2'-position was designed and synthesized via simple synthetic procedures under mild reaction conditions.The watersoluble pro...A novel BINOL-based fluorescence probe(S)-6 featuring a sodium sulfonate fragment at the 2'-position was designed and synthesized via simple synthetic procedures under mild reaction conditions.The watersoluble probe(S)-6 displays excellent enantioselective recognition toward 15 common amino acids,and it can be used for enantiomeric excess determination of amino acids.The fluorescence intensity of(S)-6 treated with amino acids reaches the maximum after standing for only 30 min at room temperature and remains stable in the following 5.5 h,which has great potential in the application of chiral fluorescence analysis due to its timeliness and outstanding fluorescent stability.展开更多
基金We are very grateful for the financial support of the National Natural Science Foundation of China (No.29872016) and the Hong Kong Polytechnic University ASD Fund.
文摘A chiral phosphorous derivatizing agent prepared from PCl3 and (S)-BINOL was described. It is used to determine the enantiomeric excess of chiral alcohols and amines by 31P NMR.
文摘Simulated enantiomeric excess of glutamic acid was determined by a lab-made sixteen-channel capillary array electrophoresis with confocal fluorescent rotary scanner. The experimental results indicated that the capillary array electrophoresis method can accurately determine the enanfiomefic excess of glutamic acid and can be used for high-throughput screening system for combinatorial asymmetric catalysis.
文摘Enantiomer of n-pyrrolidinyl phenylpropanol was studied by capillary electrophoresis using b-cyclodextrin polymer as chiral selector. We determined the enantiomeric excess value of n-pyrrolidinyl phenylpropanol with RSD 0.48%.
基金This work was kindly supported by the National Natural Science Foundation of China(No.30471153,30170621and 21023478).
文摘Using four β-cyclodextrin derivatives, 2,6-di-O-benzyl-3-O-heptanonyl-β-CD, 2,6-di- O-benzyl-3-O-octanonyl-β-CD, 2,3-di-O-benzyl-6-O-heptanonyl-β-CD, and 2,3-di-O-benzyl -6-O- octanonyl-β-CD, as chiral stationary phases of capillary gas chromatography （CGC）, the enantiomers of Sharpless epoxides were well separated. The enantiomer excess values （e.e.%） of some chiral Sharpless epoxides were also determined successfully using these CDs.
基金This work was financially supported by the State Key Laboratory of Elemento-Organic Chemistry,Nankai University.
文摘Four types of chiral thiazolidine derivatives were synthesized conveniently from natural L-cysteine and showed good enantioselectivity in up to 90% ee in the addition of diethylzine to benzaldehyde. Their enantioselectivity was affected by the bulkiness of R and the thiazolidine ring systems in their molecules.
基金the National Natural Science Foundation of China (22072050 and 22372066) for financial support。
文摘Chiral tetraphenylethylene(TPE) dicycle tetraaldehyde and TPE dicycle tetraacids bearing optically pure groups on the cycles were designed and synthesized. Due to the propeller-like conformation immobilization of TPE unit, this new class of TPE dicycle was resolved into M-and P-enantiomers, which could emit strong circular polarized luminescence(CPL). Interestingly,these TPE helicates displayed exceptional ability of molecule recognition. While the TPE dicycle tetraaldehyde could detect the microscale water in anhydrous tetrahydrofuran, the chiral TPE dicycle tetraacid could display different fluorescent color after interacting with two enantiomers of a wide variety of chiral amines including monoamines, diamines, and aminols, which could be applied to chiral recognition of these chiral amines. Furthermore, the emission wavelength of TPE dicycle tetraacid was found to change linearly with the enantiomer purity of chiral amine from enantiomer excess(ee) percent-100% to +100%, for the first time showing the potential for quantitative chiral analysis of chiral amines based on emission wavelength change. The emission wavelength was affected less by environmental factors than fluorescence intensity, which would enable the chiral analysis based on wavelength change with higher accuracy and repeatability.
基金financial support from the National Natural Science Foundation of China(Nos.21877087,22074114)Natural Science Foundation of Hubei Province of China(Nos.2020CFB623,2021CFB556)+3 种基金Key Laboratory for Green Chemical Process of Ministry of Education(No.GCP20200201)Hubei Key Laboratory of Novel Reactor and Green Chemical Technology(No.40201002)Wuhan Institute of Technology Graduate Education and Teaching Reform Research Project(Nos.2022JYXM09,2021JYXM07)Wuhan Institute of Technology Graduate Innovation Fund(Nos.CX2022450,CX2022009,CX2022058)are greatly appreciated.
文摘A novel BINOL-based fluorescence probe(S)-6 featuring a sodium sulfonate fragment at the 2'-position was designed and synthesized via simple synthetic procedures under mild reaction conditions.The watersoluble probe(S)-6 displays excellent enantioselective recognition toward 15 common amino acids,and it can be used for enantiomeric excess determination of amino acids.The fluorescence intensity of(S)-6 treated with amino acids reaches the maximum after standing for only 30 min at room temperature and remains stable in the following 5.5 h,which has great potential in the application of chiral fluorescence analysis due to its timeliness and outstanding fluorescent stability.
