Solid phase peptide synthesis using side-chain unprotected arginine and histidine with Oxyma Pure/TBEC in green solvents†

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2024-09-18 DOI:10.1039/D4GC03209H

Tommaso Fantoni, Andrea Orlandin, Ilaria Di Stefano, Marco Macis, Alessandra Tolomelli, Antonio Ricci, Walter Cabri and Lucia Ferrazzano

引用次数: 0

Abstract

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.

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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†。

消除精氨酸和组氨酸的侧链正交保护基团对于提高固相肽合成（SPPS）的可持续性至关重要，因为这样可以提高肽原子的经济性（AE），减少最后裂解步骤中产生的杂质。将 Oxyma Pure 和叔丁基乙基碳二亚胺 (TBEC) 以正确的比例结合使用，可以在绿色溶剂中使用不含侧链的精氨酸和组氨酸。在优化的条件下，通过 SPPS 成功合成了依曲塞肽和血管加压素中间体以及利拉鲁肽和赛马鲁肽的关键关键片段。此外，Oxyma Pure/TBEC 方案在 NBP/DMC 中成功应用于含有侧链未受保护的精氨酸、组氨酸、色氨酸和酪氨酸的序列。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

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.