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Selective chiral recognition of alanine enantiomers by chiral calix[4]arene coated quartz crystal microbalance sensors

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Abstract

We describe the synthesis of new chiral calix[4]arene derivatives having (R)-1-phenylethylamine, (S)-1-phenylethylamine, (R)-2-phenylglycinol, and (S)-2-phenylglycinol moieties, and chiral recognition studies for enantiomers of some selected α-amino acid derivatives such as alanine, phenylalanine, serine, and tryptophan using a quartz crystal microbalance (QCM). Initial experiments indicated that the highest selective chiral recognition factor was 1.42 for alanine enantiomers. The sensitivity, limit of detection, and time constant for l-alanine were calculated as 0.028 Hz/μM, 60.9 μM, and 36.2 s, respectively. The results indicated that real-time, sensitive, selective, and effective chiral recognition of alanine enantiomers was achieved with a QCM sensor coated with a chiral calix[4]arene derivative having (R)-2-phenylglycinol moieties.

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Acknowledgements

We thank the Technical Research Council of Turkey (TUBITAK grant number 115Z249) and the Research Foundation of Selçuk University (SUBAP grant number 16401003), Konya, Turkey, and for financial support of this work produced from FT’s Ph.D. thesis.

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Authors and Affiliations

  1. Department of Chemical Engineering, Konya Technical University, 42130, Konya, Turkey

    Farabi Temel, Merve Akpinar & Mustafa Tabakci

  2. Department of Chemical Engineering, Selçuk University, 42130, Konya, Turkey

    Farabi Temel, Merve Akpinar & Mustafa Tabakci

  3. Department of Chemistry, Selçuk University, 42130, Konya, Turkey

    Serkan Erdemir & Begum Tabakci

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Temel, F., Erdemir, S., Tabakci, B. et al. Selective chiral recognition of alanine enantiomers by chiral calix[4]arene coated quartz crystal microbalance sensors. Anal Bioanal Chem 411, 2675–2685 (2019). https://doi.org/10.1007/s00216-019-01705-5

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