{"title":"芳香醚作为杯[6]芳烃衍生物溶剂的发展及氨基酸和蛋白质的提取","authors":"Tatsuya Oshima, Tokiya Asano, Asuka Inada, Keisuke Ohto, Jumina","doi":"10.1007/s10847-022-01132-7","DOIUrl":null,"url":null,"abstract":"<div><p>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 <sup>t</sup>Oct[6]CH<sub>2</sub>COOH 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 <sup>t</sup>Oct[6]CH<sub>2</sub>COOH host in OB and BB. The cationic lysine-rich protein cytochrome <i>c</i> was also extracted using <sup>t</sup>Oct[6]CH<sub>2</sub>COOH in BB as shown for <sup>t</sup>Oct[6]CH<sub>2</sub>COOH in chloroform in previous studies. However, cytochrome <i>c</i> was not extracted using <sup>t</sup>Oct[6]CH<sub>2</sub>COOH in OB and instead, precipitated. As <sup>t</sup>Oct[6]CH<sub>2</sub>COOH stabilizes the ammonium group of biomolecules because of its suitable cavity size, the extraction of the tryptophan ester and cytochrome <i>c</i> using <sup>t</sup>Oct[6]CH<sub>2</sub>COOH 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.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.3000,"publicationDate":"2022-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s10847-022-01132-7.pdf","citationCount":"2","resultStr":"{\"title\":\"Development of aromatic ethers as solvents for a calix[6]arene derivative and extraction of amino acids and proteins\",\"authors\":\"Tatsuya Oshima, Tokiya Asano, Asuka Inada, Keisuke Ohto, Jumina\",\"doi\":\"10.1007/s10847-022-01132-7\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>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 <sup>t</sup>Oct[6]CH<sub>2</sub>COOH 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 <sup>t</sup>Oct[6]CH<sub>2</sub>COOH host in OB and BB. The cationic lysine-rich protein cytochrome <i>c</i> was also extracted using <sup>t</sup>Oct[6]CH<sub>2</sub>COOH in BB as shown for <sup>t</sup>Oct[6]CH<sub>2</sub>COOH in chloroform in previous studies. However, cytochrome <i>c</i> was not extracted using <sup>t</sup>Oct[6]CH<sub>2</sub>COOH in OB and instead, precipitated. As <sup>t</sup>Oct[6]CH<sub>2</sub>COOH stabilizes the ammonium group of biomolecules because of its suitable cavity size, the extraction of the tryptophan ester and cytochrome <i>c</i> using <sup>t</sup>Oct[6]CH<sub>2</sub>COOH 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.</p></div>\",\"PeriodicalId\":638,\"journal\":{\"name\":\"Journal of Inclusion Phenomena and Macrocyclic Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.3000,\"publicationDate\":\"2022-02-21\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://link.springer.com/content/pdf/10.1007/s10847-022-01132-7.pdf\",\"citationCount\":\"2\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Inclusion Phenomena and Macrocyclic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s10847-022-01132-7\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"Agricultural and Biological Sciences\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s10847-022-01132-7","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"Agricultural and Biological Sciences","Score":null,"Total":0}
Development of aromatic ethers as solvents for a calix[6]arene derivative and extraction of amino acids and proteins
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.
期刊介绍:
The Journal of Inclusion Phenomena and Macrocyclic Chemistry is the premier interdisciplinary publication reporting on original research into all aspects of host-guest systems. Examples of specific areas of interest are: the preparation and characterization of new hosts and new host-guest systems, especially those involving macrocyclic ligands; crystallographic, spectroscopic, thermodynamic and theoretical studies; applications in chromatography and inclusion polymerization; enzyme modelling; molecular recognition and catalysis by inclusion compounds; intercalates in biological and non-biological systems, cyclodextrin complexes and their applications in the agriculture, flavoring, food and pharmaceutical industries; synthesis, characterization and applications of zeolites.
The journal publishes primarily reports of original research and preliminary communications, provided the latter represent a significant advance in the understanding of inclusion science. Critical reviews dealing with recent advances in the field are a periodic feature of the journal.