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Enantiomeric separation of glycidyl tosylate by CE: application to the study of catalytic asymmetric epoxidation of allyl alcohol.
Electrophoresis. 2008 Nov; 29(22):4575-82.E

Abstract

A CE method using CDs as chiral selectors was developed and validated to achieve the separation of glycidyl tosylate enantiomers originated by in situ derivatization of glycidol enantiomers obtained in asymmetric epoxidation of allyl alcohol with chiral titanium-tartrate complexes as catalysts. The effects of the nature, pH and concentration of the buffer, the nature and concentration of chiral selector, the addition of SDS, methanol, ethanol or 2-propanol, the capillary temperature, the effective capillary length and the applied voltage on the chiral resolution of glycidyl tosylate enantiomers were investigated. The best separation conditions were achieved using a Tris-borate buffer mixture (50 and 25 mM, respectively) at pH=9.3 with a dual CD system consisting of 2.5% succinyl-beta-CD and 1.0% beta-CD w/v at 15 degrees C. A baseline separation (resolution approximately 2.0) of the glycidyl tosylate enantiomers was obtained in a relatively short time (less than 12 min). Satisfactory results were obtained in terms of linearity (r>0.99) and intermediate precision (RSD below 8.5%). The LOD and LOQ were 3.0 and 10.0 mg/L, respectively, and the recoveries ranged from 99.8 to 108.8%. Finally, the method was applied to the determination of the enantiomeric excess and the yield obtained in the asymmetric epoxidation of allyl alcohol employing chiral titanium-tartrate complexes as catalysts after an in situ derivatization of glycidol enantiomers to glycidyl tosylate.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Morante-Zarcero S
Departamento de Química Analítica, Facultad de Química, Universidad de Alcalá, Madrid, Spain.
Crego AL
No affiliation info available
del Hierro I
No affiliation info available
Sierra I
No affiliation info available
Marina ML
No affiliation info available

MeSH

AlgorithmsAnalysis of VarianceBuffersCatalysisCyclodextrinsElectrophoresis, CapillaryLinear ModelsReproducibility of ResultsSensitivity and SpecificityStereoisomerismTosyl Compounds

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19035381

Citation

Morante-Zarcero, Sonia, et al. "Enantiomeric Separation of Glycidyl Tosylate By CE: Application to the Study of Catalytic Asymmetric Epoxidation of Allyl Alcohol." Electrophoresis, vol. 29, no. 22, 2008, pp. 4575-82.
Morante-Zarcero S, Crego AL, del Hierro I, et al. Enantiomeric separation of glycidyl tosylate by CE: application to the study of catalytic asymmetric epoxidation of allyl alcohol. Electrophoresis. 2008;29(22):4575-82.
Morante-Zarcero, S., Crego, A. L., del Hierro, I., Sierra, I., & Marina, M. L. (2008). Enantiomeric separation of glycidyl tosylate by CE: application to the study of catalytic asymmetric epoxidation of allyl alcohol. Electrophoresis, 29(22), 4575-82. https://doi.org/10.1002/elps.200800162
Morante-Zarcero S, et al. Enantiomeric Separation of Glycidyl Tosylate By CE: Application to the Study of Catalytic Asymmetric Epoxidation of Allyl Alcohol. Electrophoresis. 2008;29(22):4575-82. PubMed PMID: 19035381.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantiomeric separation of glycidyl tosylate by CE: application to the study of catalytic asymmetric epoxidation of allyl alcohol. AU - Morante-Zarcero,Sonia, AU - Crego,Antonio L, AU - del Hierro,Isabel, AU - Sierra,Isabel, AU - Marina,Maria Luisa, PY - 2008/11/28/pubmed PY - 2009/4/21/medline PY - 2008/11/28/entrez SP - 4575 EP - 82 JF - Electrophoresis JO - Electrophoresis VL - 29 IS - 22 N2 - A CE method using CDs as chiral selectors was developed and validated to achieve the separation of glycidyl tosylate enantiomers originated by in situ derivatization of glycidol enantiomers obtained in asymmetric epoxidation of allyl alcohol with chiral titanium-tartrate complexes as catalysts. The effects of the nature, pH and concentration of the buffer, the nature and concentration of chiral selector, the addition of SDS, methanol, ethanol or 2-propanol, the capillary temperature, the effective capillary length and the applied voltage on the chiral resolution of glycidyl tosylate enantiomers were investigated. The best separation conditions were achieved using a Tris-borate buffer mixture (50 and 25 mM, respectively) at pH=9.3 with a dual CD system consisting of 2.5% succinyl-beta-CD and 1.0% beta-CD w/v at 15 degrees C. A baseline separation (resolution approximately 2.0) of the glycidyl tosylate enantiomers was obtained in a relatively short time (less than 12 min). Satisfactory results were obtained in terms of linearity (r>0.99) and intermediate precision (RSD below 8.5%). The LOD and LOQ were 3.0 and 10.0 mg/L, respectively, and the recoveries ranged from 99.8 to 108.8%. Finally, the method was applied to the determination of the enantiomeric excess and the yield obtained in the asymmetric epoxidation of allyl alcohol employing chiral titanium-tartrate complexes as catalysts after an in situ derivatization of glycidol enantiomers to glycidyl tosylate. SN - 1522-2683 UR - https://www.unboundmedicine.com/medline/citation/19035381/Enantiomeric_separation_of_glycidyl_tosylate_by_CE:_application_to_the_study_of_catalytic_asymmetric_epoxidation_of_allyl_alcohol_ L2 - https://doi.org/10.1002/elps.200800162 DB - PRIME DP - Unbound Medicine ER -