{"title":"超声辅助固相多肽合成的绿色混合溶剂:一种快速多用途方法及其在流程和天然产物合成中的应用","authors":"Jingyuan Liao, Renrong Zhang, Xuelei Jia, Meiling Wang, Chaoyi Li, Juntao Wang, Renjin Tang, Junrong Huang, Hengzhi You, Fen-Er Chen","doi":"10.1039/d4gc03864a","DOIUrl":null,"url":null,"abstract":"Peptides and depsipeptides play a significant role in diverse fields. Solid-phase peptide synthesis (SPPS) is the most renowned protocol for peptide production and can be coordinated with several process intensification techniques such as microwave, ultrasound, and continuous-flow. Until recently, most SPPS was carried out in <em>N</em>,<em>N</em>-dimethylformamide (DMF). However, the use of DMF has been restricted in the European Union since December 2023. Here we introduce a versatile <em>N</em>-formylmorpholine (NFM)/anisole (An) 1 : 1 solvent mixture that meets all green solvent criteria for SPPS. This innovation enables the first green ultrasound-assisted SPPS (US-GSPPS) and uses OxymaB to avoid hazardous benzotriazole-based compounds or OxymaPure coupling additives. Broad feasibility is demonstrated by successful synthesis of challenging peptides and natural products through on-resin esterification and solution/on-resin macrocyclization under ultrasound in NFM/An. Additionally, this mixture also functions as the first green solvent for continuous-flow solid-phase protocols.","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":null,"pages":null},"PeriodicalIF":9.3000,"publicationDate":"2024-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Green solvent mixture for ultrasound-assisted solid-phase peptide synthesis: a fast and versatile method and its applications in flow and natural product synthesis\",\"authors\":\"Jingyuan Liao, Renrong Zhang, Xuelei Jia, Meiling Wang, Chaoyi Li, Juntao Wang, Renjin Tang, Junrong Huang, Hengzhi You, Fen-Er Chen\",\"doi\":\"10.1039/d4gc03864a\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Peptides and depsipeptides play a significant role in diverse fields. Solid-phase peptide synthesis (SPPS) is the most renowned protocol for peptide production and can be coordinated with several process intensification techniques such as microwave, ultrasound, and continuous-flow. Until recently, most SPPS was carried out in <em>N</em>,<em>N</em>-dimethylformamide (DMF). However, the use of DMF has been restricted in the European Union since December 2023. Here we introduce a versatile <em>N</em>-formylmorpholine (NFM)/anisole (An) 1 : 1 solvent mixture that meets all green solvent criteria for SPPS. This innovation enables the first green ultrasound-assisted SPPS (US-GSPPS) and uses OxymaB to avoid hazardous benzotriazole-based compounds or OxymaPure coupling additives. Broad feasibility is demonstrated by successful synthesis of challenging peptides and natural products through on-resin esterification and solution/on-resin macrocyclization under ultrasound in NFM/An. Additionally, this mixture also functions as the first green solvent for continuous-flow solid-phase protocols.\",\"PeriodicalId\":78,\"journal\":{\"name\":\"Green Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":9.3000,\"publicationDate\":\"2024-09-09\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Green Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d4gc03864a\",\"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://doi.org/10.1039/d4gc03864a","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Green solvent mixture for ultrasound-assisted solid-phase peptide synthesis: a fast and versatile method and its applications in flow and natural product synthesis
Peptides and depsipeptides play a significant role in diverse fields. Solid-phase peptide synthesis (SPPS) is the most renowned protocol for peptide production and can be coordinated with several process intensification techniques such as microwave, ultrasound, and continuous-flow. Until recently, most SPPS was carried out in N,N-dimethylformamide (DMF). However, the use of DMF has been restricted in the European Union since December 2023. Here we introduce a versatile N-formylmorpholine (NFM)/anisole (An) 1 : 1 solvent mixture that meets all green solvent criteria for SPPS. This innovation enables the first green ultrasound-assisted SPPS (US-GSPPS) and uses OxymaB to avoid hazardous benzotriazole-based compounds or OxymaPure coupling additives. Broad feasibility is demonstrated by successful synthesis of challenging peptides and natural products through on-resin esterification and solution/on-resin macrocyclization under ultrasound in NFM/An. Additionally, this mixture also functions as the first green solvent for continuous-flow solid-phase protocols.
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.