Academic Journal
Efficient enantioresolution of aromatic α-hydroxy acids with Cinchona alkaloid-based zwitterionic stationary phases and volatile polar-ionic eluents
| العنوان: | Efficient enantioresolution of aromatic α-hydroxy acids with Cinchona alkaloid-based zwitterionic stationary phases and volatile polar-ionic eluents |
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| المؤلفون: | Varfaj I., Protti M., Di Michele A., Macchioni A., Lindner W., Carotti A., Sardella R., Mercolini L. |
| المساهمون: | Varfaj I., Protti M., Di Michele A., Macchioni A., Lindner W., Carotti A., Sardella R., Mercolini L. |
| سنة النشر: | 2021 |
| المجموعة: | IRIS Università degli Studi di Bologna (CRIS - Current Research Information System) |
| مصطلحات موضوعية: | Ab-initio simulation, Aromatic α-hydroxy acid, Dry urine spot |
| الوصف: | Single enantiomers of mandelic acid (1), 3-phenyllactic acid (2), and 3-(4-hydroxyphenyl)lactic acid (3) are the subject of many fields of investigation, spanning from the pharmaceutical synthesis to that of biocompatible and biodegradable polymers, while passing from the interest towards their antimicrobial activity to their role as biomarkers of particular pathological conditions or occupational exposures to specific xenobiotics. All above mentioned issues justify the need for accurate analytical methods enabling the correct determination of the individual enantiomers. So far, all the developed liquid chromatography (LC) methods were not or hardly compatible with mass spectrometry (MS) detection. In this paper, a commercially available Cinchona-alkaloid derivative zwitterionic chiral stationary phase [that is, the CHIRALPAK® ZWIX(−)] was successfully used to optimize the enantioresolution of compounds 1–3 under polar-ionic (PI) conditions with a mobile phase consisting of an acetonitrile/methanol 95/5 (v/v) mixture with 80 mM formic acid. With the optimized conditions, enantioseparation and enantioresolution values up to 1.46 and 4.41, respectively, were obtained. In order to assess the applicability of the optimized enantioselective chromatography conditions in real-life scenarios and on MS-based systems, a proof-of-concept application was efficiently carried out by analysing dry urine spot samples spiked with 1 by means of a LC-MS system. The (S)<(R) enantiomer elution order (EEO) was established for compounds 1 and 2 by analysing a pure enantiomeric standard of known configuration. This was not possible for 3 because not commercially available. For this compound, the same EEO was identified applying a procedure based on ab initio time-dependent density-functional theory simulations coupled to electronic circular dichroism analyses. Moreover, a molecular dynamics simulation unveiled the role of the phenolic OH in compound 3 in the retention mechanism. |
| نوع الوثيقة: | article in journal/newspaper |
| وصف الملف: | ELETTRONICO |
| اللغة: | English |
| Relation: | info:eu-repo/semantics/altIdentifier/pmid/34538320; info:eu-repo/semantics/altIdentifier/wos/WOS:000693024000001; volume:1180; firstpage:1; lastpage:10; numberofpages:10; journal:ANALYTICA CHIMICA ACTA; https://hdl.handle.net/11585/838681; info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-85112519719 |
| DOI: | 10.1016/j.aca.2021.338928 |
| الاتاحة: | https://hdl.handle.net/11585/838681 https://doi.org/10.1016/j.aca.2021.338928 |
| Rights: | info:eu-repo/semantics/openAccess |
| رقم الانضمام: | edsbas.6813BAD2 |
| قاعدة البيانات: | BASE |
| DOI: | 10.1016/j.aca.2021.338928 |
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