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Development of aromatic ethers as solvents for a calix[6]arene derivative and extraction of amino acids and proteins

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Abstract

Calixarene derivatives are excellent host compounds for ionic species in liquid–liquid extraction. However, many studies using calixarene derivatives have been conducted using highly toxic chloroform as a solvent because of their poor solubility in typical hydrocarbons. In the present study, aromatic ethers were developed as solvents for calixarene derivatives to enhance their industrial applicability. The solubility of the calix[6]arene carboxylic acid derivative tOct[6]CH2COOH in 1-octoxybenzene (OB) and 1-butoxybenzene (BB) was 11.3 mM and 24.9 mM, respectively. The cationic guest molecule tryptophan methyl ester was extracted using the tOct[6]CH2COOH host in OB and BB. The cationic lysine-rich protein cytochrome c was also extracted using tOct[6]CH2COOH in BB as shown for tOct[6]CH2COOH in chloroform in previous studies. However, cytochrome c was not extracted using tOct[6]CH2COOH in OB and instead, precipitated. As tOct[6]CH2COOH stabilizes the ammonium group of biomolecules because of its suitable cavity size, the extraction of the tryptophan ester and cytochrome c using tOct[6]CH2COOH was much higher than those using the corresponding calix[4]arene and calix[8]arene derivatives. These results confirm that aromatic ethers are potential solvents for calixarene derivatives for the extraction of biomolecules.

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Acknowledgements

This research was supported by the Adaptable and Seamless Technology Transfer Program through Target-driven R&D (A-STEP, VP30118067391), of the Japan Science and Technology Agency (JST), Japan. We thank Renee Mosi, PhD, from Edanz (https://jp.edanz.com/ac) for editing a draft of this manuscript.

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  1. Department of Applied Chemistry, Faculty of Engineering, University of Miyazaki, 1-1 Gakuen Kibanadai-nishi, Miyazaki, 889-2192, Japan

    Tatsuya Oshima, Tokiya Asano & Asuka Inada

  2. Department of Chemistry and Applied Chemistry, Faculty of Science and Engineering, Saga University, 1-Honjo, Saga, 840-8502, Japan

    Keisuke Ohto

  3. Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta, 55281, Indonesia

    Jumina

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  1. Tatsuya Oshima
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Oshima, T., Asano, T., Inada, A. et al. Development of aromatic ethers as solvents for a calix[6]arene derivative and extraction of amino acids and proteins. J Incl Phenom Macrocycl Chem 102, 507–514 (2022). https://doi.org/10.1007/s10847-022-01132-7

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