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

IF 2.3 4区 化学 Q2 Agricultural and Biological Sciences Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2022-02-21 DOI:10.1007/s10847-022-01132-7
Tatsuya Oshima, Tokiya Asano, Asuka Inada, Keisuke Ohto,  Jumina
{"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,&nbsp;Tokiya Asano,&nbsp;Asuka Inada,&nbsp;Keisuke Ohto,&nbsp; 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,&nbsp;Tokiya Asano,&nbsp;Asuka Inada,&nbsp;Keisuke Ohto,&nbsp; 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}
引用次数: 2

摘要

杯芳烃衍生物是液-液萃取中离子种类的优良宿主化合物。然而,由于杯芳烃衍生物在典型碳氢化合物中的溶解度差,许多使用杯芳烃衍生物的研究都是使用剧毒的氯仿作为溶剂进行的。本研究将芳香醚作为杯芳烃衍生物的溶剂,以提高其工业适用性。杯[6]芳烃羧酸衍生物tOct[6]CH2COOH在1-八苯(OB)和1-丁氧基苯(BB)中的溶解度分别为11.3 mM和24.9 mM。在OB和BB中用tOct[6]CH2COOH宿主提取阳离子客体分子色氨酸甲酯。在BB中用tOct[6]CH2COOH提取阳离子型富赖氨酸蛋白细胞色素c,如以往研究中在氯仿中用tOct[6]CH2COOH提取。然而,在OB中使用tOct[6]CH2COOH并没有提取细胞色素c,而是沉淀。由于tOct[6]CH2COOH因其适宜的腔体大小而稳定了生物分子的铵基,因此使用tOct[6]CH2COOH提取色氨酸酯和细胞色素c的效率远高于使用相应的杯[4]芳烃和杯[8]芳烃衍生物。这些结果证实芳香醚是杯芳烃衍生物萃取生物分子的潜在溶剂。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

摘要图片

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
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.

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
CiteScore
3.30
自引率
8.70%
发文量
0
审稿时长
3-8 weeks
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.
期刊最新文献
Development and characterization of a cyclodextrin-based delivery system for enhanced pharmacokinetic and safety profile of oseltamivir The host behaviour of 9-phenyl-9 H-xanthene derivatives in mixtures of cyclohexanone and the methylcyclohexanone isomers Pillar[5]arene-based thiazole NHC/Pd(II) supramolecular coordinated polymer: synthesis, structure and catalytic activity in Suzuki–Miyaura reaction Prediction of the free energy of binding for cyclodextrin-steroid complexes: phase solubility and molecular dynamics studies Solid-state structures of some fluorescent macrocyclic complexes of alkali metal ions studied by single-crystal X-ray diffraction studies, vibrational spectroscopy and NMR spectroscopy: a review
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1