Tommaso Fantoni, Andrea Orlandin, Ilaria Di Stefano, Marco Macis, Alessandra Tolomelli, Antonio Ricci, Walter Cabri and Lucia Ferrazzano
{"title":"使用 Oxyma Pure/TBEC 在绿色溶剂中合成侧链未受保护的精氨酸和组氨酸的固相肽†。","authors":"Tommaso Fantoni, Andrea Orlandin, Ilaria Di Stefano, Marco Macis, Alessandra Tolomelli, Antonio Ricci, Walter Cabri and Lucia Ferrazzano","doi":"10.1039/D4GC03209H","DOIUrl":null,"url":null,"abstract":"<p >The elimination of side-chain orthogonal protective groups of arginine and histidine is critical to improve solid phase peptide synthesis (SPPS) sustainability through an increase in the peptide atom economy (AE) and decrease in impurities generated during the final cleavage step. The combination of Oxyma Pure and tertbutyl ethyl carbodiimide (TBEC) in the correct ratio allowed the use of side-chain free arginine and histidine in green solvents. Etelcalcetide and vasopressin intermediates as well as critical key fragments of liraglutide and semaglutide were successfully synthetized <em>via</em> SPPS using optimized conditions. In addition, the Oxyma Pure/TBEC protocol in NBP/DMC was successfully applied to a sequence containing side-chain unprotected arginine, histidine, tryptophan and tyrosine.</p>","PeriodicalId":9,"journal":{"name":"ACS Catalysis ","volume":null,"pages":null},"PeriodicalIF":11.3000,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/gc/d4gc03209h?page=search","citationCount":"0","resultStr":"{\"title\":\"Solid phase peptide synthesis using side-chain unprotected arginine and histidine with Oxyma Pure/TBEC in green solvents†\",\"authors\":\"Tommaso Fantoni, Andrea Orlandin, Ilaria Di Stefano, Marco Macis, Alessandra Tolomelli, Antonio Ricci, Walter Cabri and Lucia Ferrazzano\",\"doi\":\"10.1039/D4GC03209H\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >The elimination of side-chain orthogonal protective groups of arginine and histidine is critical to improve solid phase peptide synthesis (SPPS) sustainability through an increase in the peptide atom economy (AE) and decrease in impurities generated during the final cleavage step. The combination of Oxyma Pure and tertbutyl ethyl carbodiimide (TBEC) in the correct ratio allowed the use of side-chain free arginine and histidine in green solvents. Etelcalcetide and vasopressin intermediates as well as critical key fragments of liraglutide and semaglutide were successfully synthetized <em>via</em> SPPS using optimized conditions. In addition, the Oxyma Pure/TBEC protocol in NBP/DMC was successfully applied to a sequence containing side-chain unprotected arginine, histidine, tryptophan and tyrosine.</p>\",\"PeriodicalId\":9,\"journal\":{\"name\":\"ACS Catalysis \",\"volume\":null,\"pages\":null},\"PeriodicalIF\":11.3000,\"publicationDate\":\"2024-09-18\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://pubs.rsc.org/en/content/articlepdf/2024/gc/d4gc03209h?page=search\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ACS Catalysis \",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.rsc.org/en/content/articlelanding/2024/gc/d4gc03209h\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Catalysis ","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2024/gc/d4gc03209h","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
Solid phase peptide synthesis using side-chain unprotected arginine and histidine with Oxyma Pure/TBEC in green solvents†
The elimination of side-chain orthogonal protective groups of arginine and histidine is critical to improve solid phase peptide synthesis (SPPS) sustainability through an increase in the peptide atom economy (AE) and decrease in impurities generated during the final cleavage step. The combination of Oxyma Pure and tertbutyl ethyl carbodiimide (TBEC) in the correct ratio allowed the use of side-chain free arginine and histidine in green solvents. Etelcalcetide and vasopressin intermediates as well as critical key fragments of liraglutide and semaglutide were successfully synthetized via SPPS using optimized conditions. In addition, the Oxyma Pure/TBEC protocol in NBP/DMC was successfully applied to a sequence containing side-chain unprotected arginine, histidine, tryptophan and tyrosine.
期刊介绍：
ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels.
The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.
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