Yunting Liu , Jiajing Yan , Quan Yuan , Li Ma , Liya Zhou , Ying He , Guanhua Liu , Xiaoyang Yue , Yanjun Jiang
{"title":"在胶束水溶液中酶还原卤代芳基酮,提高催化性能","authors":"Yunting Liu , Jiajing Yan , Quan Yuan , Li Ma , Liya Zhou , Ying He , Guanhua Liu , Xiaoyang Yue , Yanjun Jiang","doi":"10.1039/d4gc00773e","DOIUrl":null,"url":null,"abstract":"<div><p>Enzymatic synthesis of enantiopure chiral halogenated aryl alcohols by ketoreductases (KREDs) is emerging but still challenging, due to the low solubility and slow mass transfer in aqueous media. As an eco-friendly tool for this issue, amphiphilic micelles are attractive. Herein, KRED-catalyzed reduction of halogenated aryl ketones in a TPGS-750-M formed aqueous micellar solution was conducted, achieving the corresponding chiral alcohols with moderate to excellent yields of up to 99% and remarkable enantioselectivities of >99% ee under the optimal conditions. Notably, the performance strengthening mechanisms of micelles in this process are illustrated, in which the solubilization position of the substrate plays an essential role and the substrates solubilized in the palisade layer of the micelles exhibit the highest increases in conversion and enantioselectivity. These findings provide guidance for rational design of enzyme catalysis in aqueous micellar media.</p></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":null,"pages":null},"PeriodicalIF":9.3000,"publicationDate":"2024-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Enzymatic reduction of halogenated aryl ketones in an aqueous micellar solution with enhanced catalytic performance†\",\"authors\":\"Yunting Liu , Jiajing Yan , Quan Yuan , Li Ma , Liya Zhou , Ying He , Guanhua Liu , Xiaoyang Yue , Yanjun Jiang\",\"doi\":\"10.1039/d4gc00773e\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Enzymatic synthesis of enantiopure chiral halogenated aryl alcohols by ketoreductases (KREDs) is emerging but still challenging, due to the low solubility and slow mass transfer in aqueous media. As an eco-friendly tool for this issue, amphiphilic micelles are attractive. Herein, KRED-catalyzed reduction of halogenated aryl ketones in a TPGS-750-M formed aqueous micellar solution was conducted, achieving the corresponding chiral alcohols with moderate to excellent yields of up to 99% and remarkable enantioselectivities of >99% ee under the optimal conditions. Notably, the performance strengthening mechanisms of micelles in this process are illustrated, in which the solubilization position of the substrate plays an essential role and the substrates solubilized in the palisade layer of the micelles exhibit the highest increases in conversion and enantioselectivity. These findings provide guidance for rational design of enzyme catalysis in aqueous micellar media.</p></div>\",\"PeriodicalId\":78,\"journal\":{\"name\":\"Green Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":9.3000,\"publicationDate\":\"2024-06-04\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Green Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1463926224004941\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Green Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1463926224004941","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Enzymatic reduction of halogenated aryl ketones in an aqueous micellar solution with enhanced catalytic performance†
Enzymatic synthesis of enantiopure chiral halogenated aryl alcohols by ketoreductases (KREDs) is emerging but still challenging, due to the low solubility and slow mass transfer in aqueous media. As an eco-friendly tool for this issue, amphiphilic micelles are attractive. Herein, KRED-catalyzed reduction of halogenated aryl ketones in a TPGS-750-M formed aqueous micellar solution was conducted, achieving the corresponding chiral alcohols with moderate to excellent yields of up to 99% and remarkable enantioselectivities of >99% ee under the optimal conditions. Notably, the performance strengthening mechanisms of micelles in this process are illustrated, in which the solubilization position of the substrate plays an essential role and the substrates solubilized in the palisade layer of the micelles exhibit the highest increases in conversion and enantioselectivity. These findings provide guidance for rational design of enzyme catalysis in aqueous micellar media.
期刊介绍:
Green Chemistry is a journal that provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998), which defines green chemistry as the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry aims to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. The journal welcomes submissions on all aspects of research relating to this endeavor and publishes original and significant cutting-edge research that is likely to be of wide general appeal. For a work to be published, it must present a significant advance in green chemistry, including a comparison with existing methods and a demonstration of advantages over those methods.