避免多肽合成的隐性成本:DMI中的THIQ作为一种替代的fmoc脱保护试剂

IF 7.1 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Ming Chen, Fangxiang Sun, Gangqiang Yang
{"title":"避免多肽合成的隐性成本:DMI中的THIQ作为一种替代的fmoc脱保护试剂","authors":"Ming Chen, Fangxiang Sun, Gangqiang Yang","doi":"10.1021/acssuschemeng.5c02739","DOIUrl":null,"url":null,"abstract":"For over half a century, piperidine in <i>N</i>,<i>N</i>-dimethylformamide (PPR/DMF) has served as the gold standard for fluorenylmethyloxycarbonyl (Fmoc) deprotection in solid-phase peptide synthesis (SPPS), praised for its cost-effectiveness and robust performance. However, shifting priorities now place greater emphasis on occupational health, environmental impact, and production safety rather than simply minimizing raw material costs. As peptide synthesis scales up, it faces increasing global regulatory pressures. Traditional PPR/DMF reagents, known for their strong odor, instability, and poor material compatibility, are increasingly unsuited to modern peptide synthesis requirements. This study identifies tetrahydroisoquinoline in <i>N</i>,<i>N</i>′-dimethylimidazolidinone (THIQ/DMI) as a viable alternative, providing comparable deprotection efficiency while mitigating these drawbacks. Our findings suggest that, despite the apparent affordability and efficiency of PPR/DMF, the hidden costs associated with its use render THIQ/DMI a more sustainable and economically favorable choice.","PeriodicalId":25,"journal":{"name":"ACS Sustainable Chemistry & Engineering","volume":"145 1","pages":""},"PeriodicalIF":7.1000,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Avoiding the Hidden Costs of Peptide Synthesis: THIQ in DMI as an Alternative Fmoc-Deprotection Reagent\",\"authors\":\"Ming Chen, Fangxiang Sun, Gangqiang Yang\",\"doi\":\"10.1021/acssuschemeng.5c02739\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"For over half a century, piperidine in <i>N</i>,<i>N</i>-dimethylformamide (PPR/DMF) has served as the gold standard for fluorenylmethyloxycarbonyl (Fmoc) deprotection in solid-phase peptide synthesis (SPPS), praised for its cost-effectiveness and robust performance. However, shifting priorities now place greater emphasis on occupational health, environmental impact, and production safety rather than simply minimizing raw material costs. As peptide synthesis scales up, it faces increasing global regulatory pressures. Traditional PPR/DMF reagents, known for their strong odor, instability, and poor material compatibility, are increasingly unsuited to modern peptide synthesis requirements. This study identifies tetrahydroisoquinoline in <i>N</i>,<i>N</i>′-dimethylimidazolidinone (THIQ/DMI) as a viable alternative, providing comparable deprotection efficiency while mitigating these drawbacks. Our findings suggest that, despite the apparent affordability and efficiency of PPR/DMF, the hidden costs associated with its use render THIQ/DMI a more sustainable and economically favorable choice.\",\"PeriodicalId\":25,\"journal\":{\"name\":\"ACS Sustainable Chemistry & Engineering\",\"volume\":\"145 1\",\"pages\":\"\"},\"PeriodicalIF\":7.1000,\"publicationDate\":\"2025-06-18\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ACS Sustainable Chemistry & Engineering\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acssuschemeng.5c02739\",\"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":"ACS Sustainable Chemistry & Engineering","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acssuschemeng.5c02739","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0

摘要

半个多世纪以来,N,N-二甲基甲酰胺(PPR/DMF)中的哌啶一直是固相肽合成(SPPS)中氟酰甲基氧羰基(Fmoc)脱保护的金标准,因其成本效益和强大的性能而备受赞誉。然而,现在优先事项的变化更加强调职业健康、环境影响和生产安全,而不仅仅是尽量减少原材料成本。随着多肽合成规模的扩大,它面临着越来越大的全球监管压力。传统的PPR/DMF试剂因其强烈的气味、不稳定性和材料相容性差而越来越不适合现代肽合成的要求。本研究确定了N,N ' -二甲基咪唑烷酮(THIQ/DMI)中的四氢异喹啉作为可行的替代品,在减轻这些缺点的同时提供相当的去保护效率。我们的研究结果表明,尽管PPR/DMF具有明显的可负担性和效率,但与其使用相关的隐性成本使THIQ/DMI成为更可持续和经济上有利的选择。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Avoiding the Hidden Costs of Peptide Synthesis: THIQ in DMI as an Alternative Fmoc-Deprotection Reagent

Avoiding the Hidden Costs of Peptide Synthesis: THIQ in DMI as an Alternative Fmoc-Deprotection Reagent
For over half a century, piperidine in N,N-dimethylformamide (PPR/DMF) has served as the gold standard for fluorenylmethyloxycarbonyl (Fmoc) deprotection in solid-phase peptide synthesis (SPPS), praised for its cost-effectiveness and robust performance. However, shifting priorities now place greater emphasis on occupational health, environmental impact, and production safety rather than simply minimizing raw material costs. As peptide synthesis scales up, it faces increasing global regulatory pressures. Traditional PPR/DMF reagents, known for their strong odor, instability, and poor material compatibility, are increasingly unsuited to modern peptide synthesis requirements. This study identifies tetrahydroisoquinoline in N,N′-dimethylimidazolidinone (THIQ/DMI) as a viable alternative, providing comparable deprotection efficiency while mitigating these drawbacks. Our findings suggest that, despite the apparent affordability and efficiency of PPR/DMF, the hidden costs associated with its use render THIQ/DMI a more sustainable and economically favorable choice.
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
ACS Sustainable Chemistry & Engineering
ACS Sustainable Chemistry & Engineering CHEMISTRY, MULTIDISCIPLINARY-ENGINEERING, CHEMICAL
CiteScore
13.80
自引率
4.80%
发文量
1470
审稿时长
1.7 months
期刊介绍: ACS Sustainable Chemistry & Engineering is a prestigious weekly peer-reviewed scientific journal published by the American Chemical Society. Dedicated to advancing the principles of green chemistry and green engineering, it covers a wide array of research topics including green chemistry, green engineering, biomass, alternative energy, and life cycle assessment. The journal welcomes submissions in various formats, including Letters, Articles, Features, and Perspectives (Reviews), that address the challenges of sustainability in the chemical enterprise and contribute to the advancement of sustainable practices. Join us in shaping the future of sustainable chemistry and engineering.
×
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
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
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 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术官方微信