Green solvent mixture for ultrasound-assisted solid-phase peptide synthesis: a fast and versatile method and its applications in flow and natural product synthesis

IF 9.3 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY Green Chemistry Pub Date : 2024-09-09 DOI:10.1039/d4gc03864a

Jingyuan Liao, Renrong Zhang, Xuelei Jia, Meiling Wang, Chaoyi Li, Juntao Wang, Renjin Tang, Junrong Huang, Hengzhi You, Fen-Er Chen

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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 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.

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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

肽和副肽在不同领域发挥着重要作用。固相肽合成（SPPS）是最著名的肽生产方案，可与多种工艺强化技术（如微波、超声和连续流）配合使用。直到最近，大多数 SPPS 都是在 N,N-二甲基甲酰胺（DMF）中进行的。然而，欧盟自 2023 年 12 月起限制使用 DMF。在此，我们介绍一种多功能的 N-甲酰基吗啉（NFM）/苯甲醚（An）1 ：1 的混合溶剂，符合 SPPS 的所有绿色溶剂标准。这项创新首次实现了绿色超声辅助 SPPS（US-GSPPS），并使用 OxymaB 来避免使用有害的苯并三唑类化合物或 OxymaPure 偶联添加剂。通过在 NFM/An 中的超声条件下进行树脂上酯化和溶液/树脂上大环化，成功合成了具有挑战性的多肽和天然产物，证明了该方法的广泛可行性。此外，这种混合物还是第一种用于连续流固相方案的绿色溶剂。

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来源期刊

Green Chemistry 化学-化学综合

CiteScore

16.10

自引率

7.10%

发文量

677

审稿时长

1.4 months

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.

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