化学
劈理(地质)
环肽
水溶液
肽合成
三氟乙酸
肽
二硫键
键裂
组合化学
二甲基甲酰胺
固相合成
肽键
有机化学
化学合成
立体化学
氨基酸
寡肽
高分子化学
半胱氨酸
拟肽
有机合成
作者
Jan Pawlas,Thilda Qvist,Linda M. Haugaard‐Kedström
标识
DOI:10.1021/acs.joc.5c01493
摘要
Universal Fmoc/t-Bu solid-phase peptide synthesis (SPPS) has long been intertwined with harmful substances such as dimethylformamide (DMF) and PFAS-classified trifluoroacetic acid (TFA). Having eliminated DMF and TFA from peptide synthesis by aqueous SPPS (ASPPS) [Pawlas, J.; Rasmussen, J. H. Circular Aqueous Fmoc/t-Bu Solid-Phase Peptide Synthesis. ChemSusChem 2021, 14, 3231-3236] and Brønsted acid-Lewis acid-induced resin cleavage [Pawlas, J.; André, C.; Rasmussen, J. H.; Ludemann-Hombourger, O. Brønsted Acid-Lewis Acid (BA-LA) Induced Final Deprotection/Peptide Resin Cleavage in Fmoc/t-Bu Solid-Phase Peptide Synthesis: HCl/FeCl3 and AcOH/FeCl3 as Viable PFAS-Free Alternatives for TFA. Org. Lett. 2024, 26, 6787-6791], we now report that ASPPS can be integrated with disulfide formation and TFA/PFA-free cleavage toward a new platform for sustainable synthesis of cyclic peptides, illustrated by synthesizing labor suppressant atosiban by both on-resin cyclization/cleavage and cleavage/solution cyclization approaches.
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